Synthesis 2012; 44(10): 1535-1541
DOI: 10.1055/s-0031-1290818
special topic
© Georg Thieme Verlag Stuttgart · New York

Functional Group Tolerable Synthesis of Allylsilanes through Copper-Catalyzed γ-Selective Allyl–Alkyl Coupling between Allylic Phosphates and Alkylboranes

Kazunori Nagao
Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan, Fax: +81(11)7063749   Email: ohmiya@sci.hokudai.ac.jp   Email: sawamura@sci.hokudai.ac.jp
,
Hirohisa Ohmiya*
Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan, Fax: +81(11)7063749   Email: ohmiya@sci.hokudai.ac.jp   Email: sawamura@sci.hokudai.ac.jp
,
Masaya Sawamura*
Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan, Fax: +81(11)7063749   Email: ohmiya@sci.hokudai.ac.jp   Email: sawamura@sci.hokudai.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 06 March 2012

Accepted after revision: 13 March 2012

Publication Date:
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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