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Highly Regio- and Stereoselective Synthesis of Boron-Substituted Enynes via Copper-Catalyzed Borylation of Conjugated Diynes

Author:
Li, DingXi, Kim, Yeong Eun, Yun, Jaesook
Source:
Organic letters 2015 v.17 no.4 pp. 860-863
ISSN:
1523-7052
Subject:
chemical reactions, chemical structure, organic compounds, regioselectivity, stereoselective synthesis, stereoselectivity
Abstract:
A mild copper-catalyzed regio- and stereoselective monoborylation of conjugated diynes with bis(pinacolato)diboron that affords enynylboronates is reported. The reaction is efficient for different types of conjugated diynes including unsymmetrical diynes and produces enynylboron compounds with high and complementary regioselectivity compared with classical hydrometalation reactions. In particular, the reactions of internal conjugated diynes with a silyl substitution produced highly functionalized enynes with high regio- and stereoselectivity, which can be used in further transformations.
Agid:
5790243