Literature DB >> 25308802

Copper-catalyzed reductive cross-coupling of nonactivated alkyl tosylates and mesylates with alkyl and aryl bromides.

Jing-Hui Liu1, Chu-Ting Yang, Xiao-Yu Lu, Zhen-Qi Zhang, Ling Xu, Mian Cui, Xi Lu, Bin Xiao, Yao Fu, Lei Liu.   

Abstract

A copper-catalyzed reductive cross-coupling reaction of nonactivated alkyl tosylates and mesylates with alkyl and aryl bromides was developed. It provides a practical method for efficient and cost-effective construction of aryl-alkyl and alkyl-alkyl CC bonds with stereocontrol from readily available substrates. When used in an intramolecular fashion, the reaction enables convenient access to various substituted carbo- or heterocycles, such as 2,3-dihydrobenzofuran and benzochromene derivatives.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CC bond formation; catalysis; copper; cross-coupling; cyclization

Year:  2014        PMID: 25308802     DOI: 10.1002/chem.201405223

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


  15 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

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.  Nickel-Catalyzed Alkyl-Alkyl Cross-Electrophile Coupling Reaction of 1,3-Dimesylates for the Synthesis of Alkylcyclopropanes.

Authors:  Amberly B Sanford; Taylor A Thane; Tristan M McGinnis; Pan-Pan Chen; Xin Hong; Elizabeth R Jarvo
Journal:  J Am Chem Soc       Date:  2020-03-04       Impact factor: 15.419

4.  Harnessing Alkyl Amines as Electrophiles for Nickel-Catalyzed Cross Couplings via C-N Bond Activation.

Authors:  Corey H Basch; Jennie Liao; Jianyu Xu; Jacob J Piane; Mary P Watson
Journal:  J Am Chem Soc       Date:  2017-04-05       Impact factor: 15.419

5.  Alcohols as Latent Coupling Fragments for Metallaphotoredox Catalysis: sp3-sp2 Cross-Coupling of Oxalates with Aryl Halides.

Authors:  Xiaheng Zhang; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2016-10-17       Impact factor: 15.419

6.  Stereospecific Nickel-Catalyzed Reductive Cross-Coupling of Alkyl Tosylate and Allyl Alcohol Electrophiles.

Authors:  Quentin D Tercenio; Erik J Alexanian
Journal:  Org Lett       Date:  2021-08-31       Impact factor: 6.072

7.  The N,N,O-Trisubstituted Hydroxylamine Isostere and Its Influence on Lipophilicity and Related Parameters.

Authors:  Jarvis Hill; David Crich
Journal:  ACS Med Chem Lett       Date:  2022-04-20       Impact factor: 4.632

8.  Electrochemically driven cross-electrophile coupling of alkyl halides.

Authors:  Wen Zhang; Lingxiang Lu; Wendy Zhang; Yi Wang; Skyler D Ware; Jose Mondragon; Jonas Rein; Neil Strotman; Dan Lehnherr; Kimberly A See; Song Lin
Journal:  Nature       Date:  2022-02-21       Impact factor: 69.504

9.  Chromium-catalyzed cyclopropanation of alkenes with bromoform in the presence of 2,3,5,6-tetramethyl-1,4-bis(trimethylsilyl)-1,4-dihydropyrazine.

Authors:  Hideaki Ikeda; Kohei Nishi; Hayato Tsurugi; Kazushi Mashima
Journal:  Chem Sci       Date:  2020-03-11       Impact factor: 9.825

10.  Nickel-catalyzed migratory alkyl-alkyl cross-coupling reaction.

Authors:  Yangyang Li; Yuqiang Li; Long Peng; Dong Wu; Lei Zhu; Guoyin Yin
Journal:  Chem Sci       Date:  2020-09-09       Impact factor: 9.825

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