Literature DB >> 35499249

Directed Ni-Catalyzed Reductive Arylation of Aliphatic C-H Bonds.

Zhi-Yun Liu1, Silas P Cook1.   

Abstract

Herein, we describe the nickel-catalyzed reductive arylation of remote C(sp3)-H bonds with aryl electrophiles. The reaction targets secondary and tertiary C(sp3)-H bonds to deliver all-carbon quaternary centers. The success of this method relies on a novel amidyl radical precursor that tolerates reducing conditions, namely O-oxalate hydroxamic acid esters.

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Year:  2022        PMID: 35499249      PMCID: PMC9558148          DOI: 10.1021/acs.orglett.2c00447

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.072


  58 in total

Review 1.  Aryl-aryl bond formation by transition-metal-catalyzed direct arylation.

Authors:  Dino Alberico; Mark E Scott; Mark Lautens
Journal:  Chem Rev       Date:  2007-01       Impact factor: 60.622

2.  Transition metal-catalyzed arylation of unactivated C(sp3)-H bonds.

Authors:  Olivier Baudoin
Journal:  Chem Soc Rev       Date:  2011-04-20       Impact factor: 54.564

3.  Visible light photoredox-catalysed remote C-H functionalisation enabled by 1,5-hydrogen atom transfer (1,5-HAT).

Authors:  Weisi Guo; Qian Wang; Jieping Zhu
Journal:  Chem Soc Rev       Date:  2021-05-20       Impact factor: 54.564

Review 4.  Complementary Strategies for Directed C(sp3 )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Authors:  John C K Chu; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2017-12-05       Impact factor: 15.336

Review 5.  Transition-metal-catalyzed direct arylation of (hetero)arenes by C-H bond cleavage.

Authors:  Lutz Ackermann; Rubén Vicente; Anant R Kapdi
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

6.  Radical-Mediated Remote Functional Group Migration.

Authors:  Xinxin Wu; Chen Zhu
Journal:  Acc Chem Res       Date:  2020-07-24       Impact factor: 22.384

7.  Iron-Catalyzed, Fluoroamide-Directed C-H Fluorination.

Authors:  Brian J Groendyke; Deyaa I AbuSalim; Silas P Cook
Journal:  J Am Chem Soc       Date:  2016-09-27       Impact factor: 15.419

8.  Catalytic functionalization of C(sp2)-H and C(sp3)-H bonds by using bidentate directing groups.

Authors:  Guy Rouquet; Naoto Chatani
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-17       Impact factor: 15.336

9.  Copper-Catalyzed, Chloroamide-Directed Benzylic C-H Difluoromethylation.

Authors:  Xiaojun Zeng; Wenhao Yan; Matthew Paeth; Samson B Zacate; Pei-Hsun Hong; Yufei Wang; Dongqi Yang; Kundi Yang; Tao Yan; Chang Song; Zhi Cao; Mu-Jeng Cheng; Wei Liu
Journal:  J Am Chem Soc       Date:  2019-12-06       Impact factor: 15.419

10.  Palladium- and copper-catalyzed arylation of carbon-hydrogen bonds.

Authors:  Olafs Daugulis; Hien-Quang Do; Dmitry Shabashov
Journal:  Acc Chem Res       Date:  2009-08-18       Impact factor: 22.384

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