Literature DB >> 22697415

Nickel-catalyzed reductive coupling of aryl halides with secondary alkyl bromides and allylic acetate.

Shulin Wang1, Qun Qian, Hegui Gong.   

Abstract

A room-temperature Ni-catalyzed reductive method for the coupling of aryl bromides with secondary alkyl bromides has been developed, providing C(sp(2))-C(sp(3)) products in good to excellent yields. Slight modification of this protocol allows efficient coupling of activated aryl chlorides with cyclohexyl bromide and aryl bromides with allylic acetate.

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Year:  2012        PMID： 22697415     DOI： 10.1021/ol3013342

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  35 in total

1.  Metallaphotoredox-Catalyzed Cross-Electrophile Csp3-Csp3 Coupling of Aliphatic Bromides.

Authors:  Russell T Smith; Xiaheng Zhang; Juan A Rincón; Javier Agejas; Carlos Mateos; Mario Barberis; Susana García-Cerrada; Oscar de Frutos; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2018-12-10       Impact factor: 15.419

2.  Nickel-catalyzed reductive conjugate addition to enones via allylnickel intermediates.

Authors:  Ruja Shrestha; Stephanie C M Dorn; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2013-01-08       Impact factor: 15.419

3.  Nickel-catalyzed cross-electrophile coupling of 2-chloropyridines with alkyl bromides.

Authors:  Daniel A Everson; Joseph A Buonomo; Daniel J Weix
Journal:  Synlett       Date:  2014-01       Impact factor: 2.454

4.  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

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.  Mechanism and selectivity in nickel-catalyzed cross-electrophile coupling of aryl halides with alkyl halides.

Authors:  Soumik Biswas; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2013-10-21       Impact factor: 15.419

7.  A Dual Palladium and Copper Hydride Catalyzed Approach for Alkyl-Aryl Cross-Coupling of Aryl Halides and Olefins.

Authors:  Stig D Friis; Michael T Pirnot; Lauren N Dupuis; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-16       Impact factor: 15.336

8.  Selective cross-coupling of organic halides with allylic acetates.

Authors:  Lukiana L Anka-Lufford; Michael R Prinsell; Daniel J Weix
Journal:  J Org Chem       Date:  2012-11-06       Impact factor: 4.354

9.  Nickel-Catalyzed Cross-Coupling of Aryl Halides with Alkyl Halides: Ethyl 4-(4-(4-methylphenylsulfonamido)-phenyl)butanoate.

Authors:  Daniel A Everson; David T George; Daniel J Weix; Jonas F Buergler; John L Wood
Journal:  Organic Synth       Date:  2013

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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