Alkene Dialkylation by Triple Radical Sorting
Publications
2025
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Aminoalkylation of Alkenes Enabled by Triple Radical Sorting.
2024
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Parallel Proteomic and Transcriptomic Microenvironment Mapping (µMap) of Nuclear Condensates in Living Cells
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Iron-Catalyzed Cross-Electrophile Coupling for the Formation of All-Carbon Quaternary Centers
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μMap-Interface: Temporal Photoproximity Labeling Identifies F11R as a Functional Member of the Transient Phagocytic Surfaceome
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µMap proximity labeling in living cells reveals stress granule disassembly mechanism.
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Unlocking Carbene Reactivity by Metallaphotoredox α-Elimination.
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Engaging Alkenes in Metallaphotoredox: A Triple Catalytic, Radical Sorting Approach to Olefin-Alcohol Cross Coupling
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Current advances in photocatalytic proximity labeling
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Triple Radical Sorting: Aryl-Alyklation of Alkenes
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Free-Radical Deoxygenative Amination of Alcohols via Copper Metallaphotoredox Catalysis
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Development of a General Organophosphorus Radical Trap: Deoxyphosphonylation of Alcohols
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Direct Bioisostere Replacement Enabled by Metallaphotoredox Deoxydifluoromethylation
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Couple-close Construction of Polycyclic Rings from Diradicals
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Alcohol-alcohol cross-coupling enabled by SH2 radical sorting
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Redefining the Synthetic Logic of Medicinal Chemistry. Photoredox- Catalyzed Reactions as a General Tool for Aliphatic Core Functionalization
2023
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Exploiting the Marcus inverted region for first-row transition metal–based photoredox catalysis
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One-Pot Synthesis of Sulfonamides from Unactivated Acids and Amines via Aromatic Decarboxylative Halosulfonylation
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Photoredox Catalysis-Enabled Sulfination of Alcohols and Bromides
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Rapid and Modular Access to Quaternary Carbons from Tertiary Alcohols via Bimolecular Homolytic Substitution
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μMap Photoproximity Labeling Enables Small Molecule Binding Site Mapping
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General Access to Cubanes as Benzene Bioisosteres
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Tracking chromatin state changes using nanoscale photo-proximity labelling
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Expedient Access to Underexplored Chemical Space: Deoxygenative C(sp3)–C(sp3) Cross-Coupling
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Late-Stage C(sp3)−H Methylation of Drug Molecules
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Rapid Access to 2‐Substituted Bicyclo[1.1.1]pentanes
2022
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Photoproximity Labeling of Sialylated Glycoproteins (GlycoMap) Reveals Sialylation-Dependent Regulation of Ion Transport
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Carboxylic Acids as Adaptive Functional Groups in Metallaphotoredox Catalysis
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Nickel Catalysis via SH2 Homolytic Substitution: The Double Decarboxylative Cross-Coupling of Aliphatic Acids
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Photochemical Identification of Auxiliary Severe Acute Respiratory Syndrome Coronavirus 2 Host Entry Factors Using μMap
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Radius measurement via super-resolution microscopy enables the development of a variable radii proximity labeling platform
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Deoxytrifluoromethylation of Alcohols
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Alcohols as Alkylating Agents: Photoredox-Catalyzed Conjugate Alkylation via In Situ Deoxygenation
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Bioinspired Supercharging of Photoredox Catalysis for Applications in Energy and Chemical Manufacturing
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Accelerating reaction generality and mechanistic insight through additive mapping
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A Unified Approach to Decarboxylative Halogenation of (Hetero)aryl Carboxylic Acids
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Decarboxylative Borylation and Cross-Coupling of (Hetero)aryl Acids Enabled by Copper Charge Transfer Catalysis
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μMap-Red: Proximity Labeling by Red Light Photocatalysis
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Nontraditional Fragment Couplings of Alcohols and Carboxylic Acids: C(sp3)–C(sp3) Cross-Coupling via Radical Sorting
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Metallaphotoredox: The Merger of Photoredox and Transition Metal Catalysis
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Selective Isomerization via Transient Thermodynamic Control: Dynamic Epimerization of trans to cis Diols
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Small molecule photocatalysis enables drug target identification via energy transfer
2021
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A biohybrid strategy for enabling photoredox catalysis with low-energy light
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A biomimetic SH2 cross-coupling mechanism for quaternary sp3-carbon formation
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Metallaphotoredox-enabled deoxygenative arylation of alcohols
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Synthesis of Enantiopure Unnatural Amino Acids by Metallaphotoredox Catalysis
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Site-selective tyrosine bioconjugation via photoredox catalysis for native-to-bioorthogonal protein transformation
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Decatungstate-Catalyzed C(sp3)−H Sulfinylation: Rapid Access to Diverse Organosulfur Functionality
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A general N-alkylation platform via copper metallaphotoredox and silyl radical activation of alkyl halides
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The Application of Pulse Radiolysis to the Study of Ni(I) Intermediates in Ni-Catalyzed Cross-Coupling Reactions
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Rapid Optimization of Photoredox Reactions for Continuous-Flow Systems Using Microscale Batch Technology
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Reactive intermediates for interactome mapping
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Metallaphotoredox aryl and alkyl radiomethylation for PET ligand discovery
2020
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Site-Selective Functionalization of Methionine Residues via Photoredox Catalysis
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Metallaphotoredox Perfluoroalkylation of Organobromide
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Decarboxylative Oxygenation via Photoredox Catalysis
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Mechanistic Analysis of Metallaphotoredox C−N Coupling:Photocatalysis Initiates and Perpetuates Ni(I)/Ni(III) Coupling Activity
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Static to inducibly dynamic stereocontrol: The convergent use of racemic β-substituted ketones
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HARC as an open-shell strategy to bypass oxidative addition in Ullmann–Goldberg couplings
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Cross-Electrophile Coupling of Unactivated Alkyl Chlorides
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The merger of decatungstate and copper catalysis to enable aliphatic C(sp3)–H trifluoromethylation
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Microenvironment mapping via Dexter energy transfer on immune cells
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Copper-mediated synthesis of drug-like bicyclopentanes
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Transient Absorption Spectroscopy Offers Mechanistic Insights for an Iridium/Nickel-Catalyzed C−O Coupling
2019
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Open-Shell Fluorination of Alkyl Bromides: Unexpected Selectivity in a Silyl Radical-Mediated Chain Process
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A Metallaphotoredox Strategy for the Cross-Electrophile Coupling of Alpha-Chloro Carbonyls with Aryl Halides
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Photoredox-catalyzed deoxyfluorination of activated alcohols with Selectfluor
**Tetrahedron Prize for Creativity in Organic Chemistry, Steve Buchwald
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Copper-Catalyzed Trifluoromethylation of Alkyl Bromides
2018
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Metallaphotoredox-Catalyzed Cross-Electrophile Csp3−Csp3 Coupling of Aliphatic Bromides
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Metallaphotoredox Difluoromethylation of Aryl Bromides
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Direct arylation of strong aliphatic C–H bonds
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Decarboxylative sp3 C–N coupling via dual copper and photoredox catalysis
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A radical approach to the copper oxidative addition problem: Trifluoromethylation of bromoarenes
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Decarboxylative Trifluoromethylation of Aliphatic Carboxylic Acids
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Decarboxylative Hydroalkylation of Alkynes
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Selective Hydrogen Atom Abstraction through Induced Bond Polarization: Direct α-Arylation of Alcohols through Photoredox, HAT, and Nickel Catalysis
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Sulfonamidation of Aryl and Heteroaryl Halides through Photosensitized Nickel Catalysis
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Spin-Center Shift-Enabled Direct Enantioselective α-Benzylation of Aldehydes with Alcohols
2017
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Decarboxylative alkylation for site-selective bioconjugation of native proteins via oxidation potentials
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Photoredox-catalyzed deuteration and tritiation of pharmaceutical compounds
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Direct Aldehyde C–H Arylation and Alkylation via the Combination of Nickel, Hydrogen Atom Transfer, and Photoredox Catalysis
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Catalyst-Controlled Oligomerization for the Collective Synthesis of Polypyrroloindoline Natural Products
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The Merger of Transition Metal and Photocatalysis
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Direct, Enantioselective α-Alkylation of Aldehydes using Simple Olefins
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Selective sp3 C–H Alkylation via Polarity-Match-Based Cross-Coupling
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A General Small-Scale Reactor to Enable Standardization and Acceleration of Photocatalytic Reactions
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Photosensitized, Energy Transfer-Mediated Organometallic Catalysis Through Electronically Excited Nickel(II)
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Decarboxylative Peptide Macrocyclization through Photoredox Catalysis
2016
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Alcohols as Latent Coupling Fragments for Metallaphotoredox Catalysis: sp3–sp2 Cross-Coupling of Oxalates with Aryl Halides
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Metallaphotoredox-Catalysed sp3–sp3 Cross-Coupling of Carboxylic Acids with Alkyl Halides
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Photoredox Catalysis in Organic Chemistry
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Aryl Amination Using Ligand-Free Ni(II) Salts and Photoredox Catalysis
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Silyl Radical Activation of Alkyl Halides in Metallaphotoredox Catalysis: A Unique Pathway for Cross-Electrophile Coupling
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Native Functionality in Triple Catalytic Cross-Coupling: sp3 C–H Bonds as Latent Nucleophiles
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Oxy-Allyl Cation Catalysis: An Enantioselective Electrophilic Activation Mode
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Enantioselective Decarboxylative Arylation of α-Amino Acids via the Merger of Photoredox and Nickel Catalysis
2015
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Fragment Couplings via CO2 Extrusion−Recombination: Expansion of a Classic Bond-Forming Strategy via Metallaphotoredox
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Oxalates as Activating Groups for Alcohols in Visible Light Photoredox Catalysis: Formation of Quaternary Centers by Redox-Neutral Fragment Coupling
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O–H Hydrogen Bonding Promotes H-Atom Transfer from a C–H bonds for α-Alkylation of Alcohols
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Alcohols as Alkylating Agents in Heteroarene C–H Functionalization
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Switching on Elusive Organometallic Mechanisms with Photoredox Catalysis
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Enantioselective α-Alkylation of Aldehydes by Photoredox Organocatalysis: Rapid Access to Pharmacophore Fragments from β-Cyanoaldehydes
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Selective Radical−Radical Cross-Couplings: Design of a Formal β‑Mannich Reaction
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Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones by the Decarboxylative Arylation of α-Oxo Acids
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Decarboxylative Fluorination of Aliphatic Carboxylic Acids via Photoredox Catalysis
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The Direct Arylation of Allylic sp3 C–H Bonds via Organic and Photoredox Catalysis
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Merging Photoredox and Nickel Catalysis: Decarboxylative Cross-Coupling of Carboxylic Acids with Vinyl Halides
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Direct α-Arylation of Ethers through the Combination of Photoredox–Mediated C–H Functionalization and the Minisci Reaction
2014
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Activation of C−H Bonds via the Merger of Photoredox and Organocatalysis: A Coupling of Benzylic Ethers with Schiff Bases
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Amine α-Heteroarylation via Photoredox Catalysis: A Homolytic Aromatic Substitution Pathway
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Photoredox α‑Vinylation of α‑Amino Acids and N‑Aryl Amines
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Carboxylic Acids as A Traceless Activation Group for Conjugate Additions: A Three-Step Synthesis of (±)-Pregabalin
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Merging Photoredox with Nickel Catalysis: Coupling of α-Carboxyl sp3-Carbons with Aryl Halides
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Direct β‑Alkylation of Aldehydes via Photoredox Organocatalysis
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A General and Enantioselective Approach to Pentoses: A Rapid Synthesis of PSI-6130, the Nucleoside Core of Sofosbuvir
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Decarboxylative Arylation of α‑Amino Acids via Photoredox Catalysis: A One-Step Conversion of Biomass to Drug Pharmacophore
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A General Strategy for Organocatalytic Activation of C−H Bonds via Photoredox Catalysis: Direct Arylation of Benzylic Ethers
2013
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Direct β‑Functionalization of Cyclic Ketones with Aryl Ketones via the Merger of Photoredox and Organocatalysis
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Simple Catalytic Mechanism for the Direct Coupling of α‑Carbonyls with Functionalized Amines: A One-Step Synthesis of Plavix
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Enantioselective Total Synthesis of (−)-Minovincine in Nine Chemical Steps: An Approach to Ketone Activation in Cascade Catalysis
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Enantioselective α‑Alkenylation of Aldehydes with Boronic Acids via the Synergistic Combination of Copper(II) and Amine Catalysis
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Enantioselective Direct α‑Amination of Aldehydes via a Photoredox Mechanism: A Strategy for Asymmetric Amine Fragment Coupling
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Enantioselective Intramolecular Aldehyde α‑Alkylation with Simple Olefins: Direct Access to Homo-Ene Products
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Development of a generic activation mode: nucleophilic α-substitution of ketones via oxy-allyl cations
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Nine-Step Enantioselective Total Synthesis of (−)-Vincorine
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Photoredox Activation for the Direct β-Arylation of Ketones and Aldehydes
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Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis
2012
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Enantioselective Organo-SOMO Cycloadditions: A Catalytic Approach to Complex Pyrrolidines from Olefins and Aldehydes
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Enantioselective Copper-Catalyzed Construction of Aryl Pyrroloindolines via an Arylation−Cyclization Cascade
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Enantioselective α-Vinylation of Aldehydes via the Synergistic Combination of Copper and Amine Catalysis
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Synergistic Catalysis: A Powerful Synthetic Strategy for New Reaction Development
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A General Approach to the Enantioselective α-Oxidation of Aldehydes via Synergistic Catalysis
2011
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Trifluoromethylation of arenes and heteroarenes by means of photoredox catalysis
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Discovery of an α-Amino C–H Arylation Reaction Using the Strategy of Accelerated Serendipity
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Enantioselective α-Arylation of Carbonyls via Cu(I)-Bisoxazoline Catalysis
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Collective Synthesis of Natural Products By Means of Organocascade Catalysis
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Photoredox Catalysis: A Mild, Operationally Simple Approach to the Synthesis of α-Trifluoromethyl Carbonyl Compounds
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The Intramolecular Asymmetric Allylation of Aldehydes via Organo-SOMO Catalysis: A Novel Approach to Ring Construction
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Enantioselective α-Arylation of Aldehydes via the Productive Merger of Iodonium Salts and Organocatalysis
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Enantioselective Organocatalytic α-Fluorination of Cyclic Ketones
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Total Synthesis of Diazonamide A
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The Preparation of (2R,5S)-2-t-butyl-3,5- Dimethylimidazolidin-4-one
2010
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Direct and Enantioselective α-Allylation of Ketones via Singly Occupied Molecular Orbital (SOMO) Catalysis
*** Special Issue on Organocatalysis
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Enantioselective α-Benzylation of Aldehydes via Photoredox Organocatalysis
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Mechanistic Complexity in Organo–SOMO Activation
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Enantioselective Organo-SOMO Cascade Cycloadditions: A Rapid Approach to Molecular Complexity from Simple Aldehydes and Olefins
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Concerning the Mechanism of the FeCl3-Catalyzed α–Oxyamination of Aldehydes: Evidence for a Non-SOMO Activation Pathway
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The Organocatalytic Three-Step Total Synthesis of (+)-Frondosin B
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Nature of Intermediates in Organo-SOMO Catalysis of α-Arylation of Aldehydes
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Enantioselective Polyene Cyclization via Organo-SOMO Catalysis
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The Productive Merger of Iodonium Salts and Organocatalysis: A Non-photolytic Approach to the Enantioselective α-Trifluoromethylation of Aldehydes
2009
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Nine-Step Enantioselective Total Synthesis of (+)-Minfiensine
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Development of a General, Enantioselective Organocatalytic Mukaiyama–Michael Reaction with α,β-Unsaturated Aldehydes
*** Tetrahedron Prize for Creativity in Organic Chemistry, Larry Overman
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Enantioselective Aldehyde α-Nitroalkylation via Oxidative Organocatalysis
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Enantioselective α-Arylation of Aldehydes via Organo-SOMO Catalysis. An Ortho-Selective Arylation Reaction Based on an Open-Shell Pathway
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Enantioselective α-Trifluoromethylation of Aldehydes via Photoredox Organocatalysis
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Enantioselective Linchpin Catalysis by SOMO Catalysis: An Approach to the Asymmetric α-Chlorination of Aldehydes and Terminal Epoxide Formation
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Cycle-Specific Organocascade Catalysis: Application to Olefin Hydroamination, Hydro-oxidation, and Amino-oxidation, and to Natural Product Synthesis
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A Process for the Rapid Removal of Dialkylamino-Substituents From Aromatic Rings. Application to the Expedient Synthesis of (R)-Tolterodine
*** Tetrahedron Young Investigator Award, Justin Du Bois
2008
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Enantioselective Organo-Singly Occupied Molecular Orbital Catalysis: The Carbo-oxidation of Styrenes
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The Advent and Development of Organocatalysis
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Merging Photoredox Catalysis with Organocatalysis: The Direct Asymmetric Alkylation of Aldehydes
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Total Synthesis and Structural Revision of Callipeltoside C
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Enantioselective Organo-SOMO Catalysis: The α-Vinylation of Aldehydes
2007
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Enantioselective Organocatalytic Transfer Hydrogenation Reactions using Hantzsch Esters
*** Special Issue on Hydrogenation & Transfer Hydrogenation
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Organocatalytic Vinyl and Friedel–Crafts Alkylations with Trifluoroborate Salts
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Strategies to Bypass the Taxol Problem. Enantioselective Cascade Catalysis, a New Approach for the Efficient Construction of Molecular Complexity
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Enantioselective Organocatalytic Singly Occupied Molecular Orbital Activation: The Enantioselective α-Enolation of Aldehydes
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Enantioselective Organocatalysis Using SOMO Activation
2006
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Organocatalytic Transfer Hydrogenation of Cyclic Enones
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Enantioselective Organocatalytic Epoxidation Using Hypervalent Iodine Reagents
***Tetrahedron Young Investigator Award, David MacMillan
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Enantioselective Organocatalytic Amine Conjugate Addition
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Modern Strategies in Organic Catalysis: The Advent and Development of Iminium Activation
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Enantioselective Organocatalytic Reductive Amination
2005
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Enantioselective Organo-Cascade Catalysis
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Enantioselective Organocatalytic Intramolecular Diels-Alder Reactions. The Asymmetric Synthesis of Solanapyrone D
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Enantioselective Organocatalytic α-Fluorination of Aldehydes
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Total Synthesis of Brasoside and Littoralisone
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Enantioselective Organocatalytic Cyclopropanations. The Identification of a New Class of Iminium Catalyst Based upon Directed Electrostatic Activation
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Enantioselective Organocatalytic Hydride Reduction
2004
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The Importance of Iminium Geometry Control in Enamine Catalysis: Identification of a New Catalyst Architecture for Aldehyde–Aldehyde Couplings
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Two Step Synthesis of Carbohydrates by Selective Aldol Reactions
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Enantioselective Organocatalytic Aldehyde–Aldehyde Cross-Aldol Couplings. The Broad Utility of α-Thioacetal Aldehydes
*** Tetrahedron Prize for Creativity in Organic Chemistry, Dieter Seebach
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Enantioselective Organocatalytic Construction of Pyrroloindolines by a Cascade Addition–Cyclization Strategy: Synthesis of (–)-Flustramine B
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Direct and Enantioselective Organocatalytic α-Chlorination of Aldehydes
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Enantioselective Organocatalytic Direct Aldol Reactions of α-Oxyaldehydes: Step One in a Two Step Synthesis of Carbohydrates
2003
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The Direct and Enantioselective Organocatalytic α-Oxidation of Aldehydes
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The First Suzuki Cross-Couplings of Aryltrimethylammonium Salts
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The First Enantioselective Organocatalytic Mukaiyama-Michael Reaction: A Direct Method for the Synthesis of Enantioenriched γ-Butenolide Architecture
2002
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Development of a New Lewis Acid-Catalyzed [3,3]-Sigmatropic Rearrangement: The Allenoate-Claisen Rearrangement
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The Enantioselective Organocatalytic 1,4-Addition of Electron-Rich Benzenes to α,β-Unsaturated Aldehydes
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The First Direct and Enantioselective Cross-Aldol Reaction of Aldehydes
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The First General Enantioselective Catalytic Diels-Alder Reaction with Simple α,β-Unsaturated Ketones
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Enantioselective Organocatalytic Indole Alkylations. Design of a New and Highly Effective Chiral Amine for Iminium Catalysis
2001
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New Strategies in Organic Catalysis: The First Enantioselective Organocatalytic Friedel-Crafts Alkylation
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Enantioselective Claisen Rearrangements: Development of a First Generation Asymmetric Acyl-Claisen Reaction
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Design of a New Cascade Reaction for the Construction of Complex Acyclic Architecture: The Tandem Acyl-Claisen Rearrangement
2000
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New Strategies for Organic Catalysis: The First Enantioselective Organocatalytic 1,3-Dipolar Cycloaddition
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New Strategies for Organic Catalysis: The First Highly Enantioselective Organocatalytic Diels-Alder Reaction
1999
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Development of a New Lewis Acid-Catalyzed Claisen Rearrangement
Book Chapters
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Lelais, G.; MacMillan, D. W. C. History and Perspective of Chiral Organic Catalysts. In New Frontiers in Asymmetric Catalysis; Mikami, K., Lautens, M., Eds.; Wiley: Hoboken, New Jersey, 2007; pp 313–358.
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Lelais, G.; MacMillan, D. W. C. Iminium Catalysis. In Enantioselective Organocatalysis: Reactions and Experimental Procedures; Dalko, P. I., Ed.; Wiley-VCH: Weinheim, 2007; pp 95–120.
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Watson, A. J. B.; MacMillan, D. W. C. Enantioselective Organocatalysis Involving Iminium, Enamine, SOMO, and Photoredox Activation. In Catalytic Asymmetric Synthesis, 3rd ed.; Ojima, I., Ed.; Wiley: Hoboken, New Jersey, 2010, Chapter 2A, pp 39–57.
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MacMillan, D. W. C.; Watson, A. J. B. Photoredox Organocatalysis Mediated Enantioselective α-Functionalization. In Science of Synthesis: Stereoselective Synthesis 3. Evans, P.A., Ed.; Thieme: New York, New York, 2011, Chapter 16, pp 675-746.
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Prier, C. K.; MacMillan, D. W. C. Dual Photoredox Catalysis: The Merger of Photoredox Catalysis with Other Catalytic Activation Modes. In Visible Light Photocatalysis in Organic Chemistry; Stephenson, C. R. J., Yoon, T. P., MacMillan, D. W. C., Eds.; Wiley: Hoboken, New Jersey, 2018, Chapter 10, pp 299-333.