Ligand-Controlled Regiodivergent Copper-Catalyzed Alkylboration of Unactivated Terminal Alkynes

A ligand-controlled regiodivergent and stereospecific copper-catalyzed alkylboration of unactivated terminal alkynes has been developed. Anti-Markovnikov alkylboration products were obtained with dppbz as ligand; conversely, Markovnikov alkylboration products were obtained with DMAP as ligand. This...

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Bibliographic Details
Published in:ACS catalysis 2016-10, Vol.6 (10), p.6417-6421
Main Authors: Su, Wei, Gong, Tian-Jun, Zhang, Qi, Zhang, Qing, Xiao, Bin, Fu, Yao
Format: Article
Language:English
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Summary:A ligand-controlled regiodivergent and stereospecific copper-catalyzed alkylboration of unactivated terminal alkynes has been developed. Anti-Markovnikov alkylboration products were obtained with dppbz as ligand; conversely, Markovnikov alkylboration products were obtained with DMAP as ligand. This reaction not only presents a direct route to construct a vinyl C­(sp2)–C­(sp3) bond but also provides an efficient way to synthesize both internal and external vinylboronic esters regiodivergently from a single unactivated terminal alkyne.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.6b02039