Literature DB >> 29911724

Electrochemical strategies for C-H functionalization and C-N bond formation.

Markus D Kärkäs1.   

Abstract

Conventional methods for carrying out carbon-hydrogen functionalization and carbon-nitrogen bond formation are typically conducted at elevated temperatures, and rely on expensive catalysts as well as the use of stoichiometric, and perhaps toxic, oxidants. In this regard, electrochemical synthesis has recently been recognized as a sustainable and scalable strategy for the construction of challenging carbon-carbon and carbon-heteroatom bonds. Here, electrosynthesis has proven to be an environmentally benign, highly effective and versatile platform for achieving a wide range of nonclassical bond disconnections via generation of radical intermediates under mild reaction conditions. This review provides an overview on the use of anodic electrochemical methods for expediting the development of carbon-hydrogen functionalization and carbon-nitrogen bond formation strategies. Emphasis is placed on methodology development and mechanistic insight and aims to provide inspiration for future synthetic applications in the field of electrosynthesis.

Entities:  

Year:  2018        PMID: 29911724     DOI: 10.1039/c7cs00619e

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  56 in total

1.  Modifying Positional Selectivity in C-H Functionalization Reactions with Nitrogen-Centered Radicals: Generalizable Approaches to 1,6-Hydrogen-Atom Transfer Processes.

Authors:  Melanie A Short; J Miles Blackburn; Jennifer L Roizen
Journal:  Synlett       Date:  2019-11-27       Impact factor: 2.454

2.  Combined Photoredox/Enzymatic C-H Benzylic Hydroxylations.

Authors:  Rick C Betori; Catherine M May; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-26       Impact factor: 15.336

Review 3.  Catalyzing Electrosynthesis: A Homogeneous Electrocatalytic Approach to Reaction Discovery.

Authors:  Juno C Siu; Niankai Fu; Song Lin
Journal:  Acc Chem Res       Date:  2020-02-20       Impact factor: 22.384

Review 4.  A Survival Guide for the "Electro-curious".

Authors:  Cian Kingston; Maximilian D Palkowitz; Yusuke Takahira; Julien C Vantourout; Byron K Peters; Yu Kawamata; Phil S Baran
Journal:  Acc Chem Res       Date:  2019-12-11       Impact factor: 22.384

5.  Electrochemical C-C bond cleavage of cyclopropanes towards the synthesis of 1,3-difunctionalized molecules.

Authors:  Pan Peng; Xingxiu Yan; Ke Zhang; Zhao Liu; Li Zeng; Yixuan Chen; Heng Zhang; Aiwen Lei
Journal:  Nat Commun       Date:  2021-05-24       Impact factor: 14.919

6.  Metal-free electrochemical fluorodecarboxylation of aryloxyacetic acids to fluoromethyl aryl ethers.

Authors:  Michael Berger; John D Herszman; Yuji Kurimoto; Goswinus H M de Kruijff; Aaron Schüll; Sven Ruf; Siegfried R Waldvogel
Journal:  Chem Sci       Date:  2020-06-01       Impact factor: 9.825

7.  Carboxylate breaks the arene C-H bond via a hydrogen-atom-transfer mechanism in electrochemical cobalt catalysis.

Authors:  Xin-Ran Chen; Shuo-Qing Zhang; Tjark H Meyer; Chun-Hui Yang; Qin-Hao Zhang; Ji-Ren Liu; Hua-Jian Xu; Fa-He Cao; Lutz Ackermann; Xin Hong
Journal:  Chem Sci       Date:  2020-05-19       Impact factor: 9.825

8.  Oxoiron(v) mediated selective electrochemical oxygenation of unactivated C-H and C[double bond, length as m-dash]C bonds using water as the oxygen source.

Authors:  Bittu Chandra; Hellan K M; Santanu Pattanayak; Sayam Sen Gupta
Journal:  Chem Sci       Date:  2020-09-24       Impact factor: 9.825

9.  Mangana(iii/iv)electro-catalyzed C(sp3)-H azidation.

Authors:  Tjark H Meyer; Ramesh C Samanta; Antonio Del Vecchio; Lutz Ackermann
Journal:  Chem Sci       Date:  2020-12-28       Impact factor: 9.825

Review 10.  Direct Photocatalyzed Hydrogen Atom Transfer (HAT) for Aliphatic C-H Bonds Elaboration.

Authors:  Luca Capaldo; Davide Ravelli; Maurizio Fagnoni
Journal:  Chem Rev       Date:  2021-08-06       Impact factor: 60.622

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