Novel Bifunctional Synthetic Reagents: gem-Dimetallic Compounds Derived from Carbenoid Reagents and Interelement Compounds.

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  • Shimizu Masaki
    Department of Material Chemistry, Graduate School of EngineeringKyoto University
  • Kurahashi Takuya
    Department of Material Chemistry, Graduate School of EngineeringKyoto University
  • Hiyama Tamejiro
    Department of Material Chemistry, Graduate School of EngineeringKyoto University

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Novel synthetic reagents with gem-silylboryl and gem-diboryls have been prepared through formation of an ate complex from a lithium carbenoid and an interelement compound such as (dimethylphenylsilyl) (pinacolato) borane or bis (pinacolato) diboron, followed by 1, 2-migration of the silyl or boryl group from a negatively charged boron to the carbenoid carbon. Alkenylidene-type carbenoids afforded 1-boryl-1-silyl-1-alkenes and 1, 1-diboryl-1-alkenes, applicable to boron-mediated coupling reactions. Reaction of α-chloroallyllithiums with the silylborane gave 1-boryl-1-silyl-2-alkenes, which were shown to serve as a versatile reagent for stereodivergent allylation leading to 4-oxy-(E)-alkenylboronates and 4-oxy-(Z)- alkenylsilanes. 1-Boryl-1-silylallenes were synthesized from 3-acyloxy- or 3-chloroalkynyllithium and the silylborane. Furthermore, novel synthesis and application of 2, 3-diboryl-1, 3-dienes are presented.

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