Literature DB >> 28984886

Copper(i)-catalyzed 5-exo-trig radical cyclization/borylation of alkyl halides: access to functionalized pyrrolidine derivatives.

Jie Cui1, Hui Wang, Jian Song, Xiaochen Chi, Long Meng, Qing Liu, Daopeng Zhang, Yunhui Dong, Hui Liu.   

Abstract

This work reports the copper(i)-catalyzed 5-exo-trig radical cyclization/borylation of alkyl halides bearing an alkene moiety, during which a C-C bond and a C-B bond were formed in one step. Various functionalized pyrrolidine derivatives bearing a quaternary carbon center were obtained, and they showed good functional group tolerance and high chemoselectivity. This transformation was highly efficient and could be finished in 20 minutes. A radical mechanism has been proposed.

Entities:  

Year:  2017        PMID: 28984886     DOI: 10.1039/c7ob01831b

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  2 in total

Review 1.  New avenues for C-B bond formation via radical intermediates.

Authors:  Florian W Friese; Armido Studer
Journal:  Chem Sci       Date:  2019-09-03       Impact factor: 9.825

2.  Construction of congested Csp3-Csp3 bonds by a formal Ni-catalyzed alkylboration.

Authors:  Amit Kumar Simlandy; Stephen R Sardini; M Kevin Brown
Journal:  Chem Sci       Date:  2021-03-09       Impact factor: 9.825

  2 in total

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