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Copper‐Catalyzed Stereoselective Defluorinative Borylation and Silylation of gem ‐Difluoroalkenes
Author(s) -
Tan DongHang,
Lin E,
Ji WeiWei,
Zeng YaoFu,
Fan WenXin,
Li Qingjiang,
Gao Hui,
Wang Honggen
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701497
Subject(s) - borylation , chemistry , silylation , stereoselectivity , silanes , catalysis , substrate (aquarium) , olefin fiber , silylene , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , silicon , aryl , alkyl , oceanography , silane , geology
The copper‐catalyzed stereoselective defluorinative borylation and silylation of gem ‐difluoroalkenes was developed. The protocol led to the exclusive formation of Z type monofluoroalkenyl borons and silanes in generally good efficiency with broad substrate scope. The products formed could be readily transformed to other F‐containing molecules by taking advantage of the versatile reactivities of C−B and C−Si bonds. Experimental and theoretical mechanistic studies were conducted which support an olefin insertion/ syn ‐planar β‐F elimination pathway.