Copper-Catalyzed Double Borylation of Silylacetylenes: Highly Regio- and Stereoselective Synthesis of Syn-Vicinal Diboronates
摘要：
Phosphite-copper(I) complexes efficiently catalyzed the double borylation of internal silylated alkynes to provide vicinal diboronates with excellent regio- and stereoselectivity. The copper-catalyzed reaction between bis(pinacolato)diboron (B2pin2) and aryl-substituted silylacetylenes in the presence of MeOH resulted in double syn addition of the pinacolboronate moiety (Bpin) and H across the triple bond with complete selectivity. While the double borylation was highly efficient for aryl-substituted alkynylsilanes and silylacetylene, only monoborylation took place with alkyl-substituted alkynylsilanes to yield (Z)-(β-borylvinyl)silanes under the developed catalytic conditions.
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关键词：
organo‐boron compounds diastereoselective syntheses, enantioselective syntheses (incl. cis/trans﹊somerism)
DOI：
10.1021/ol300909k
被引量：
年份：
2012
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