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Synthesis 2012; 44(10): 1535-1541
DOI: 10.1055/s-0031-1290818
DOI: 10.1055/s-0031-1290818
special topic
Functional Group Tolerable Synthesis of Allylsilanes through Copper-Catalyzed γ-Selective Allyl–Alkyl Coupling between Allylic Phosphates and Alkylboranes
Weitere Informationen
Publikationsverlauf
Received: 06. März 2012
Accepted after revision: 13. März 2012
Publikationsdatum:
19. April 2012 (online)
Abstract
A copper-catalyzed γ-selective allyl–alkyl coupling between γ-silylated allylic phosphates and alkylboron compounds (alkyl-9-BBN, prepared by hydroboration of alkenes with 9-BBN-H) produced allylsilanes. The reaction tolerated various functional groups in both the alkylboranes and the allylic phosphates, and afforded functionalized allylsilanes.
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For copper-catalyzed silylation of allylic chlorides with a silylboronate:
For related studies from our group on transition metal catalyzed γ-selective and stereospecific allylic substitutions:
For Cu-catalyzed carboxylations with alkylboron compounds (alkyl-9-BBN) to CO2:
For Cu-catalyzed γ-selective coupling between alkylboron compounds (alkyl-9-BBN) and propargylic phosphates: