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Copper(I)‐Catalyzed Regioselective Addition of Nucleophilic Silicon Across Terminal and Internal Carbon–Carbon Triple Bonds
Author(s) -
Hazra Chinmoy K.,
Fopp Carolin,
Oestreich Martin
Publication year - 2014
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201402643
Subject(s) - regioselectivity , chemistry , reagent , alkyl , alkoxide , catalysis , triple bond , carbon fibers , aryl , copper , nucleophile , silicon , combinatorial chemistry , organic chemistry , double bond , materials science , composite number , composite material
The copper(I) alkoxide‐catalyzed release of a silicon‐based cuprate reagent from a silicon–boron pronucleophile is applied to the addition across carbon–carbon triple bonds. Commercially available CuBr⋅Me 2 S was found to be a general precatalyst that secures high regiocontrol for both aryl‐ and alkyl‐substituted terminal as well as internal alkynes. The solvent greatly influences the regioisomeric ratio, favoring the linear regioisomer with terminal acceptors. This facile protocol even allows for the transformation of internal acceptors with remarkable levels of regio‐ and diastereocontrol.