Literature DB >> 33712612

Dual Ni/photoredox-catalyzed asymmetric cross-coupling to access chiral benzylic boronic esters.

Purui Zheng1,2, Pan Zhou1, Dong Wang1, Wenhao Xu1, Hepan Wang1, Tao Xu3.   

Abstract

The flourishing Ni/photoredox-catalyzed asymmetric couplings typically rely on redox-neutral reactions. In this work, we report a reductive cross-coupling of aryl iodides and α-chloroboranes under a dual catalytic regime to further enrich the metallaphotoredox chemistry. This approach proceeds under mild conditions (visible light, ambient temperature, no strong base) to access the versatile benzylic boronic esters with good functional group tolerance and excellent enantioselectivities.

Entities:  

Year:  2021        PMID: 33712612     DOI: 10.1038/s41467-021-21947-1

Source DB:  PubMed          Journal:  Nat Commun        ISSN: 2041-1723            Impact factor:   14.919


  27 in total

1.  Enantioselective Electroreductive Coupling of Alkenyl and Benzyl Halides via Nickel Catalysis.

Authors:  Travis J DeLano; Sarah E Reisman
Journal:  ACS Catal       Date:  2019-07-25       Impact factor: 13.084

Review 2.  Transition metal-catalyzed alkyl-alkyl bond formation: Another dimension in cross-coupling chemistry.

Authors:  Junwon Choi; Gregory C Fu
Journal:  Science       Date:  2017-04-14       Impact factor: 47.728

3.  Asymmetric copper-catalyzed C-N cross-couplings induced by visible light.

Authors:  Quirin M Kainz; Carson D Matier; Agnieszka Bartoszewicz; Susan L Zultanski; Jonas C Peters; Gregory C Fu
Journal:  Science       Date:  2016-02-12       Impact factor: 47.728

4.  Asymmetric Propargylic Radical Cyanation Enabled by Dual Organophotoredox and Copper Catalysis.

Authors:  Fu-Dong Lu; Dan Liu; Lei Zhu; Liang-Qiu Lu; Qian Yang; Quan-Quan Zhou; Yi Wei; Yu Lan; Wen-Jing Xiao
Journal:  J Am Chem Soc       Date:  2019-04-02       Impact factor: 15.419

5.  Nickel-Catalyzed Enantioselective Reductive Cross-Coupling Reactions.

Authors:  Kelsey E Poremba; Sara E Dibrell; Sarah E Reisman
Journal:  ACS Catal       Date:  2020-06-24       Impact factor: 13.084

6.  Enantioselective Allylic Alkylation with 4-Alkyl-1,4-dihydro-pyridines Enabled by Photoredox/Palladium Cocatalysis.

Authors:  Hong-Hao Zhang; Jia-Jia Zhao; Shouyun Yu
Journal:  J Am Chem Soc       Date:  2018-11-30       Impact factor: 15.419

7.  Dual catalysis. Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis.

Authors:  John C Tellis; David N Primer; Gary A Molander
Journal:  Science       Date:  2014-06-05       Impact factor: 47.728

8.  Enantioselective Decarboxylative Arylation of α-Amino Acids via the Merger of Photoredox and Nickel Catalysis.

Authors:  Zhiwei Zuo; Huan Cong; Wei Li; Junwon Choi; Gregory C Fu; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2016-02-05       Impact factor: 15.419

9.  Photoredox Catalysis in Organic Chemistry.

Authors:  Megan H Shaw; Jack Twilton; David W C MacMillan
Journal:  J Org Chem       Date:  2016-08-01       Impact factor: 4.354

10.  Single-Electron Transmetalation via Photoredox/Nickel Dual Catalysis: Unlocking a New Paradigm for sp(3)-sp(2) Cross-Coupling.

Authors:  John C Tellis; Christopher B Kelly; David N Primer; Matthieu Jouffroy; Niki R Patel; Gary A Molander
Journal:  Acc Chem Res       Date:  2016-07-05       Impact factor: 22.384

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  2 in total

1.  Asymmetric synthesis of aryl/vinyl alkyl carbinol esters via Ni-catalyzed reductive arylation/vinylation of 1-chloro-1-alkanol esters.

Authors:  Deli Sun; Xianghua Tao; Guobin Ma; Jifen Wang; Yunrong Chen
Journal:  Chem Sci       Date:  2022-06-27       Impact factor: 9.969

Review 2.  The Impact of Boron Hybridisation on Photocatalytic Processes.

Authors:  Alessandro Marotta; Callum E Adams; John J Molloy
Journal:  Angew Chem Int Ed Engl       Date:  2022-08-10       Impact factor: 16.823

  2 in total

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