Synthesis 2018; 50(09): 1737-1749
DOI: 10.1055/s-0036-1591777
review
© Georg Thieme Verlag Stuttgart · New York

Cu-Catalyzed Borylative and Silylative Transformations of Allenes: Use of β-Functionalized Allyl Copper Intermediates in Organic Synthesis

Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan   Email: tfuji@scl.kyoto-u.ac.jp   Email: ytsuji@scl.kyoto-u.ac.jp
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Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan   Email: tfuji@scl.kyoto-u.ac.jp   Email: ytsuji@scl.kyoto-u.ac.jp
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Further Information

Publication History

Received: 29 September 2017

Accepted after revision: 21 November 2017

Publication Date:
20 March 2018 (online)


Abstract

Herein, copper-catalyzed borylative and silylative transformations of allenes using borylcopper or silylcopper as the active catalytic species are described. First, the synthesis and characterization of borylcopper and silylcopper complexes are briefly introduced. Next, the borylative transformations of allenes are summarized including hydro­boration, carboboration, and borylative allylation of carbonyl compounds. We next deal with the silylative transformations of allenes such as hydrosilylation, carbosilylation, and silylative allylation of carbonyl compounds.

1 Introduction

2 Synthesis of Borylcopper and Silylcopper Complexes

3 Borylative Transformations

4 Silylative Transformations

5 Conclusions and Future Outlook