Literature DB >> 24825799

Reductive cross-coupling reactions between two electrophiles.

Christiane E I Knappke1, Sabine Grupe, Dominik Gärtner, Martin Corpet, Corinne Gosmini, Axel Jacobi von Wangelin.   

Abstract

Reductive cross-electrophile coupling reactions have recently been developed to a versatile and sustainable synthetic tool for selective C-C bond formation. The employment of cheap and abundant electrophiles avoids the pre-formation and handling of organometallic reagents. In situ reductive coupling is effected in the presence of a transition-metal catalyst (Ni, Co, Pd, Fe) and a suitable metallic reductant (Mn, Zn, Mg). This Concept article assesses the current state of the art and summarizes recent protocols with various combinations of alkyl, alkenyl, allyl, and aryl reagents and highlights key mechanistic studies.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  biaryls; cross-coupling; metalation; reduction; sustainable chemistry

Year:  2014        PMID: 24825799     DOI: 10.1002/chem.201402302

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  62 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

2.  Synthesis of Tetrasubstituted Alkenes by Tandem Metallacycle Formation/Cross-Electrophile Coupling.

Authors:  Kirk W Shimkin; John Montgomery
Journal:  J Am Chem Soc       Date:  2018-05-31       Impact factor: 15.419

3.  Cross-Electrophile Coupling of Vinyl Halides with Alkyl Halides.

Authors:  Keywan A Johnson; Soumik Biswas; Daniel J Weix
Journal:  Chemistry       Date:  2016-04-28       Impact factor: 5.236

Review 4.  Cross-Coupling of Heteroatomic Electrophiles.

Authors:  Katerina M Korch; Donald A Watson
Journal:  Chem Rev       Date:  2019-06-11       Impact factor: 60.622

5.  Reductive Decarboxylative Alkynylation of N-Hydroxyphthalimide Esters with Bromoalkynes.

Authors:  Liangbin Huang; Astrid M Olivares; Daniel J Weix
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-17       Impact factor: 15.336

6.  Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future.

Authors:  Louis-Charles Campeau; Nilay Hazari
Journal:  Organometallics       Date:  2018-11-27       Impact factor: 3.876

7.  Cross-Electrophile Coupling of Unactivated Alkyl Chlorides.

Authors:  Holt A Sakai; Wei Liu; Chi Chip Le; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2020-06-26       Impact factor: 15.419

8.  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

9.  Nickel/Photoredox-Catalyzed Amidation via Alkylsilicates and Isocyanates.

Authors:  Shuai Zheng; David N Primer; Gary A Molander
Journal:  ACS Catal       Date:  2017-10-25       Impact factor: 13.084

10.  Nickel-Catalyzed Asymmetric Reductive Cross-Coupling between Heteroaryl Iodides and α-Chloronitriles.

Authors:  Nathaniel T Kadunce; Sarah E Reisman
Journal:  J Am Chem Soc       Date:  2015-08-13       Impact factor: 15.419

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