skip to main content
DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

This content will become publicly available on March 17, 2021

Title: Regioselective Arene C−H Alkylation Enabled by Organic Photoredox Catalysis

Authors:
 [1];  [1]; ORCiD logo [1]
  1. Department of ChemistryUniversity of North Carolina at Chapel Hill Chapel Hill NC 27599-3290 USA
Publication Date:
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1605039
Grant/Contract Number:  
[SC0001011]
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Angewandte Chemie
Additional Journal Information:
[Journal Name: Angewandte Chemie]; Journal ID: ISSN 0044-8249
Publisher:
Wiley Blackwell (John Wiley & Sons)
Country of Publication:
Germany
Language:
English

Citation Formats

Holmberg‐Douglas, Natalie, Onuska, Nicholas P. R., and Nicewicz, David A. Regioselective Arene C−H Alkylation Enabled by Organic Photoredox Catalysis. Germany: N. p., 2020. Web. doi:10.1002/ange.202000684.
Holmberg‐Douglas, Natalie, Onuska, Nicholas P. R., & Nicewicz, David A. Regioselective Arene C−H Alkylation Enabled by Organic Photoredox Catalysis. Germany. doi:10.1002/ange.202000684.
Holmberg‐Douglas, Natalie, Onuska, Nicholas P. R., and Nicewicz, David A. Tue . "Regioselective Arene C−H Alkylation Enabled by Organic Photoredox Catalysis". Germany. doi:10.1002/ange.202000684.
@article{osti_1605039,
title = {Regioselective Arene C−H Alkylation Enabled by Organic Photoredox Catalysis},
author = {Holmberg‐Douglas, Natalie and Onuska, Nicholas P. R. and Nicewicz, David A.},
abstractNote = {},
doi = {10.1002/ange.202000684},
journal = {Angewandte Chemie},
number = ,
volume = ,
place = {Germany},
year = {2020},
month = {3}
}

Journal Article:
Free Publicly Available Full Text
This content will become publicly available on March 17, 2021
Publisher's Version of Record

Save / Share:

Works referenced in this record:

Direct C–H Cyanation of Arenes via Organic Photoredox Catalysis
journal, February 2017

  • McManus, Joshua B.; Nicewicz, David A.
  • Journal of the American Chemical Society, Vol. 139, Issue 8
  • DOI: 10.1021/jacs.6b12708

Iron and Manganese Catalysts for the Selective Functionalization of Arene C(sp 2 )−H Bonds by Carbene Insertion
journal, April 2016

  • Conde, Ana; Sabenya, Gerard; Rodríguez, Mònica
  • Angewandte Chemie International Edition, Vol. 55, Issue 22
  • DOI: 10.1002/anie.201601750

Direct Aryl C−H Amination with Primary Amines Using Organic Photoredox Catalysis
journal, November 2017

  • Margrey, Kaila A.; Levens, Alison; Nicewicz, David A.
  • Angewandte Chemie International Edition, Vol. 56, Issue 49
  • DOI: 10.1002/anie.201709523

Kinetic Separation and Asymmetric Reactions of Norcaradiene Cycloadducts: Facilitated Access via H 2 O-Accelerated Cycloaddition
journal, January 2016


Photocatalytic Alkylation of Pyrroles and Indoles with α-Diazo Esters
journal, August 2019


Copper(II) Triflate Catalyzed Intermolecular Aromatic Substitution of N,N-Disubstituted Anilines with Diazo Esters
journal, November 2010

  • Tayama, Eiji; Yanaki, Tomoyo; Iwamoto, Hajime
  • European Journal of Organic Chemistry, Vol. 2010, Issue 35
  • DOI: 10.1002/ejoc.201001083

Catalytic Carbene Insertion into C−H Bonds
journal, February 2010

  • Doyle, Michael P.; Duffy, Richard; Ratnikov, Maxim
  • Chemical Reviews, Vol. 110, Issue 2
  • DOI: 10.1021/cr900239n

Metal-Free, Visible-Light-Mediated Direct C–H Arylation of Heteroarenes with Aryl Diazonium Salts
journal, February 2012

  • Hari, Durga Prasad; Schroll, Peter; König, Burkhard
  • Journal of the American Chemical Society, Vol. 134, Issue 6
  • DOI: 10.1021/ja212099r

Radical Cation Cyclopropanations via Chromium Photooxidative Catalysis
journal, May 2017


The Conversion of tert- Butyl Esters to Acid Chlorides Using Thionyl Chloride
journal, February 2017

  • Greenberg, Jacob A.; Sammakia, Tarek
  • The Journal of Organic Chemistry, Vol. 82, Issue 6
  • DOI: 10.1021/acs.joc.6b02931

Rhodium(II)-Catalyzed Enantioselective C−H Functionalization of Indoles
journal, February 2011

  • DeAngelis, Andrew; Shurtleff, Valerie W.; Dmitrenko, Olga
  • Journal of the American Chemical Society, Vol. 133, Issue 6
  • DOI: 10.1021/ja1093309

Hydrodecarboxylation of Carboxylic and Malonic Acid Derivatives via Organic Photoredox Catalysis: Substrate Scope and Mechanistic Insight
journal, August 2015

  • Griffin, Jeremy D.; Zeller, Mary A.; Nicewicz, David A.
  • Journal of the American Chemical Society, Vol. 137, Issue 35
  • DOI: 10.1021/jacs.5b07770

Rhodium( iii )-catalyzed CF 3 -carbenoid C–H functionalization of 6-arylpurines
journal, January 2018

  • Vorobyeva, Daria V.; Vinogradov, Mikhail M.; Nelyubina, Yulia V.
  • Organic & Biomolecular Chemistry, Vol. 16, Issue 16
  • DOI: 10.1039/C8OB00645H

Generating carbyne equivalents with photoredox catalysis
journal, February 2018

  • Wang, Zhaofeng; Herraiz, Ana G.; del Hoyo, Ana M.
  • Nature, Vol. 554, Issue 7690
  • DOI: 10.1038/nature25185

Ligand and counteranion enabled regiodivergent C–H bond functionalization of naphthols with α-aryl-α-diazoesters
journal, January 2019

  • Yu, Zhunzhun; Li, Yongfeng; Zhang, Peichao
  • Chemical Science, Vol. 10, Issue 26
  • DOI: 10.1039/C9SC01657K

Iron and Manganese Catalysts for the Selective Functionalization of Arene C(sp 2 )−H Bonds by Carbene Insertion
journal, April 2016

  • Conde, Ana; Sabenya, Gerard; Rodríguez, Mònica
  • Angewandte Chemie, Vol. 128, Issue 22
  • DOI: 10.1002/ange.201601750

Reaction pathways of the cation radicals of aromatic compounds related to the anthracenes
journal, July 1984


Pd−C-Induced Catalytic Transfer Hydrogenation with Triethylsilane
journal, August 2007

  • Mandal, Pijus K.; McMurray, John S.
  • The Journal of Organic Chemistry, Vol. 72, Issue 17
  • DOI: 10.1021/jo0706123

Highly Site-Selective Direct C–H Bond Functionalization of Phenols with α-Aryl-α-diazoacetates and Diazooxindoles via Gold Catalysis
journal, May 2014

  • Yu, Zhunzhun; Ma, Ben; Chen, Mingjin
  • Journal of the American Chemical Society, Vol. 136, Issue 19
  • DOI: 10.1021/ja503163k

Das Norcaradien-Problem
journal, May 1967


Blue light-promoted photolysis of aryldiazoacetates
journal, January 2018

  • Jurberg, Igor D.; Davies, Huw M. L.
  • Chemical Science, Vol. 9, Issue 22
  • DOI: 10.1039/C8SC01165F

Site-selective arene C-H amination via photoredox catalysis
journal, September 2015


Direct Aryl C−H Amination with Primary Amines Using Organic Photoredox Catalysis
journal, November 2017

  • Margrey, Kaila A.; Levens, Alison; Nicewicz, David A.
  • Angewandte Chemie, Vol. 129, Issue 49
  • DOI: 10.1002/ange.201709523

C–H bond functionalization based on metal carbene migratory insertion
journal, January 2015

  • Hu, Fangdong; Xia, Ying; Ma, Chen
  • Chemical Communications, Vol. 51, Issue 38
  • DOI: 10.1039/C5CC00497G

Rhodium(III)-Catalyzed Azacycle-Directed Intermolecular Insertion of Arene C–H Bonds into α-Diazocarbonyl Compounds
journal, May 2013

  • Yu, Xinzhang; Yu, Songjie; Xiao, Jian
  • The Journal of Organic Chemistry, Vol. 78, Issue 11
  • DOI: 10.1021/jo400572h

The Norcaradiene Problem
journal, May 1967


Visible light C–H amidation of heteroarenes with benzoyl azides
journal, January 2015

  • Brachet, E.; Ghosh, T.; Ghosh, I.
  • Chemical Science, Vol. 6, Issue 2
  • DOI: 10.1039/C4SC02365J