Literature DB >> 25143210

The electron is a catalyst.

Armido Studer1, Dennis P Curran2.   

Abstract

The electron is an efficient catalyst for conducting various types of radical cascade reaction that proceed by way of radical and radical ion intermediates. But because electrons are omnipresent, catalysis by electrons often passes unnoticed. In this Review, a simple analogy between acid/base catalysis and redox catalysis is presented. Conceptually, the electron is a catalyst in much the same way that a proton is a catalyst. The 'electron is a catalyst' paradigm unifies mechanistically an assortment of synthetic transformations that otherwise have little or no apparent relationship. Diverse radical cascades, including unimolecular radical substitution reactions (SRN1-type chemistry), base-promoted homolytic aromatic substitutions (BHAS), radical Heck-type reactions, radical cross-dehydrogenative couplings (CDC), direct arene trifluoromethylations and radical alkoxycarbonylations, can all be viewed as electron-catalysed reactions.

Entities:  

Mesh:

Substances:

Year:  2014        PMID: 25143210     DOI: 10.1038/nchem.2031

Source DB:  PubMed          Journal:  Nat Chem        ISSN: 1755-4330            Impact factor:   24.427


  44 in total

1.  Novel 10-I-3 hypervalent iodine-based compounds for electrophilic trifluoromethylation.

Authors:  Patrick Eisenberger; Sebastian Gischig; Antonio Togni
Journal:  Chemistry       Date:  2006-03-08       Impact factor: 5.236

Review 2.  Palladium-catalyzed cross-dehydrogenative functionalization of C(sp(2))-H Bonds.

Authors:  Yinuo Wu; Jun Wang; Fei Mao; Fuk Yee Kwong
Journal:  Chem Asian J       Date:  2013-10-02

Review 3.  Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Authors:  Christopher K Prier; Danica A Rankic; David W C MacMillan
Journal:  Chem Rev       Date:  2013-03-19       Impact factor: 60.622

4.  Potassium tert-butoxide mediated Heck-type cyclization/isomerization-benzofurans from organocatalytic radical cross-coupling reactions.

Authors:  Magnus Rueping; Matthias Leiendecker; Arindam Das; Thomas Poisson; Lan Bui
Journal:  Chem Commun (Camb)       Date:  2011-09-05       Impact factor: 6.222

5.  Tin-free radical chemistry using the persistent radical effect: alkoxyamine isomerization, addition reactions and polymerizations.

Authors:  Armido Studer
Journal:  Chem Soc Rev       Date:  2004-05-18       Impact factor: 54.564

6.  Synthesis of carbazoles by intramolecular arylation of diarylamide anions.

Authors:  María E Budén; Victoria A Vaillard; Sandra E Martin; Roberto A Rossi
Journal:  J Org Chem       Date:  2009-06-19       Impact factor: 4.354

7.  Transition-metal-free alkoxycarbonylation of aryl halides.

Authors:  Hua Zhang; Renyi Shi; Anxing Ding; Lijun Lu; Borui Chen; Aiwen Lei
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-05       Impact factor: 15.336

8.  Synthesis of alkyl aryl ketones by Pd/light induced carbonylative cross-coupling of alkyl iodides and arylboronic acids.

Authors:  Shuhei Sumino; Takahito Ui; Ilhyong Ryu
Journal:  Org Lett       Date:  2013-06-03       Impact factor: 6.005

9.  Single electron transfer-induced Grignard cross-coupling involving ion radicals as exclusive intermediates.

Authors:  Nanase Uchiyama; Eiji Shirakawa; Tamio Hayashi
Journal:  Chem Commun (Camb)       Date:  2012-11-27       Impact factor: 6.222

10.  6-Aroylated phenanthridines via base promoted homolytic aromatic substitution (BHAS).

Authors:  Dirk Leifert; Constantin Gabriel Daniliuc; Armido Studer
Journal:  Org Lett       Date:  2013-11-25       Impact factor: 6.005

View more
  64 in total

1.  Domino reactions: More than just a game.

Authors:  Thomas Broja; Patrick J W Fuchs; Kirsten Zeitler
Journal:  Nat Chem       Date:  2015-12       Impact factor: 24.427

2.  Asymmetric photoredox transition-metal catalysis activated by visible light.

Authors:  Haohua Huo; Xiaodong Shen; Chuanyong Wang; Lilu Zhang; Philipp Röse; Liang-An Chen; Klaus Harms; Michael Marsch; Gerhard Hilt; Eric Meggers
Journal:  Nature       Date:  2014-11-06       Impact factor: 49.962

3.  Concepts and tools for mechanism and selectivity analysis in synthetic organic electrochemistry.

Authors:  Cyrille Costentin; Jean-Michel Savéant
Journal:  Proc Natl Acad Sci U S A       Date:  2019-05-17       Impact factor: 11.205

4.  Metal-free defluorinative arylation of trifluoromethyl alkenes via photoredox catalysis.

Authors:  Rebecca J Wiles; James P Phelan; Gary A Molander
Journal:  Chem Commun (Camb)       Date:  2019-06-14       Impact factor: 6.222

5.  Aliphatic Radical Relay Heck Reaction at Unactivated C(sp3 )-H Sites of Alcohols.

Authors:  Padon Chuentragool; Dongari Yadagiri; Taiki Morita; Sumon Sarkar; Marvin Parasram; Yang Wang; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-17       Impact factor: 15.336

Review 6.  Concerted Nucleophilic Aromatic Substitution Reactions.

Authors:  Simon Rohrbach; Andrew J Smith; Jia Hao Pang; Darren L Poole; Tell Tuttle; Shunsuke Chiba; John A Murphy
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-13       Impact factor: 15.336

7.  Mechanistic insights into the potassium tert-butoxide-mediated synthesis of N-heterobiaryls.

Authors:  David E Stephens; Johant Lakey-Beitia; Jessica E Burch; Hadi D Arman; Oleg V Larionov
Journal:  Chem Commun (Camb)       Date:  2016-08-02       Impact factor: 6.222

8.  Main Group Redox Catalysis of Organopnictogens: Vertical Periodic Trends and Emerging Opportunities in Group 15.

Authors:  Jeffrey M Lipshultz; Gen Li; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2021-01-19       Impact factor: 15.419

9.  Recent advances in the chemistry of ketyl radicals.

Authors:  Áron Péter; Soumitra Agasti; Oliver Knowles; Emma Pye; David J Procter
Journal:  Chem Soc Rev       Date:  2021-03-23       Impact factor: 54.564

10.  Testing the limits of radical-anionic CH-amination: a 10-million-fold decrease in basicity opens a new path to hydroxyisoindolines via a mixed C-N/C-O-forming cascade.

Authors:  Quintin Elliott; Gabriel Dos Passos Gomes; Christopher J Evoniuk; Igor V Alabugin
Journal:  Chem Sci       Date:  2020-02-21       Impact factor: 9.825

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.