Skip to main content
U.S. Department of Energy
Office of Scientific and Technical Information

Regioselective Radical Alkylation of Arenes Using Evolved Photoenzymes

Journal Article · · Journal of the American Chemical Society
DOI:https://doi.org/10.1021/jacs.3c03607· OSTI ID:2421185
 [1];  [2];  [3];  [4];  [4];  [5];  [5];  [3];  [4]
  1. Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14850, United States; Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States; OSTI
  2. Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14850, United States; Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States
  3. Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States
  4. Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14850, United States
  5. Prozomix, Building 4, West End Ind. Estate, Haltwhistle, Northumberland, NE49 9HN, U.K.

Not provided.

Research Organization:
Princeton Univ., NJ (United States)
Sponsoring Organization:
USDOE Office of Science (SC)
DOE Contract Number:
SC0019370
OSTI ID:
2421185
Journal Information:
Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 21 Vol. 145; ISSN 0002-7863
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English

References (47)

Transition-Metal-Catalyzed Site-Selective C–H Functionalization of Quinolines beyond C2 Selectivity journal July 2015
Late‐Stage 18F‐Difluoromethyl Labeling of N‐Heteroaromatics with High Molar Activity for PET Imaging journal August 2019
Radical-based regioselective cross-coupling of indoles and cycloalkanes journal January 2016
Quaternary Charge-Transfer Complex Enables Photoenzymatic Intermolecular Hydroalkylation of Olefins journal December 2020
Biocatalytic control of site-selectivity and chain length-selectivity in radical amino acid halogenases journal March 2023
Photoexcitation of flavoenzymes enables a stereoselective radical cyclization journal June 2019
Innate and Guided C–H Functionalization Logic journal October 2011
Palladium-Catalyzed Cross-Coupling Reactions in Total Synthesis journal July 2005
Pd-catalyzed cross-coupling reactions of alkyl halides journal January 2011
Fresh Look at Electron-Transfer Mechanisms via the Donor/Acceptor Bindings in the Critical Encounter Complex journal May 2008
Hydrogen Atom Transfer Driven Enantioselective Minisci Reaction of Alcohols journal April 2022
Structures of Complexes Formed by Halogen Molecules with Aromatic and with Oxygenated Solvents 1 journal January 1950
Charge-transfer complexes: new perspectives on an old class of compounds journal January 2014
Selectivity in the Addition of Electron‐Deficient Radicals to the C2 Position of Indoles journal September 2020
Beyond Friedel and Crafts: Innate Alkylation of C−H Bonds in Arenes journal June 2019
Nucleophilic character of alkyl radicals—II journal January 1970
Synthetic Methods Driven by the Photoactivity of Electron Donor–Acceptor Complexes journal March 2020
Transition-Metal-Catalyzed Arene Alkylation and Alkenylation: Catalytic Processes for the Generation of Chemical Intermediates journal November 2020
Arene diversification through distal C(sp 2 )−H functionalization journal May 2021
Benzophenone triplet properties in acetonitrile and water. Reduction by lactams
  • Bensasson, René V.; Gramain, Jean-Claude
  • Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases, Vol. 76, Issue 0 https://doi.org/10.1039/F19807601801
journal January 1980
Engineering a Non‐Natural Photoenzyme for Improved Photon Efficiency** journal December 2021
Photoredox Cyanomethylation of Indoles: Catalyst Modification and Mechanism journal June 2018
Direct transition metal-catalyzed functionalization of heteroaromatic compounds journal January 2007
Hydrodecarboxylation of Carboxylic and Malonic Acid Derivatives via Organic Photoredox Catalysis: Substrate Scope and Mechanistic Insight journal August 2015
A comprehensive overview of directing groups applied in metal-catalysed C–H functionalisation chemistry journal January 2018
The role of threonine 37 in flavin reactivity of the old yellow enzyme journal March 1999
Ground-State Electron Transfer as an Initiation Mechanism for Biocatalytic C–C Bond Forming Reactions journal June 2021
Ground-state charge transfer for NIR absorption with donor/acceptor molecules: interactions mediated via energetics and orbital symmetries journal January 2017
Undirected, Homogeneous C–H Bond Functionalization: Challenges and Opportunities journal May 2016
Tuning P450 Enzymes as Oxidation Catalysts journal March 2012
Strong electronic coupling in intermolecular (charge-transfer) complexes. Mechanistic relevance to thermal and optical electron transfer from aromatic donors journal June 2002
Secondary Alkyl Halides in Transition-Metal-Catalyzed Cross-Coupling Reactions journal January 2009
Enhancing electron affinity and tuning band gap in donor–acceptor organic semiconductors by benzothiadiazole directed C–H borylation journal January 2015
Asymmetric redox-neutral radical cyclization catalysed by flavin-dependent ‘ene’-reductases journal December 2019
An asymmetric sp3–sp3 cross-electrophile coupling using ‘ene’-reductases journal August 2022
Potentiometric studies of native and flavin-substituted Old Yellow Enzyme. journal November 1985
Advancements in Visible-Light-Enabled Radical C(sp)2–H Alkylation of (Hetero)arenes journal January 2019
Intermolecular oxidative cross-coupling of arenes journal January 2010
Photoenzymatic Synthesis of α-Tertiary Amines by Engineered Flavin-Dependent “Ene”-Reductases journal November 2021
Directed evolution of RebH for catalyst-controlled halogenation of indole C–H bonds journal January 2016
From C4 to C7: Innovative Strategies for Site-Selective Functionalization of Indole C–H Bonds journal March 2021
Radical-Based Regioselective C–H Functionalization of Electron-Deficient Heteroarenes: Scope, Tunability, and Predictability journal July 2013
Electrochemical reactor dictates site selectivity in N-heteroarene carboxylations journal January 2023
Photoenzymatic Generation of Unstabilized Alkyl Radicals: An Asymmetric Reductive Cyclization journal August 2020
Molecular editing of aza-arene C–H bonds by distance, geometry and chirality journal August 2022
Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance journal October 2017
Catalytic enantioselective Minisci-type addition to heteroarenes journal April 2018

Similar Records

Engineering a photoenzyme to use red light
Journal Article · 2024 · Chem · OSTI ID:2477666

Radical Termination via β-Scission Enables Photoenzymatic Allylic Alkylation Using “Ene”-Reductases
Journal Article · 2022 · ACS Catalysis · OSTI ID:1978320

Regioselective Arene C−H Alkylation Enabled by Organic Photoredox Catalysis
Journal Article · 2020 · Angewandte Chemie · OSTI ID:1605039

Related Subjects