Copper(I)-Catalyzed Regio- and Stereoselective Silaboration of Terminal Allenes

Yu Ozawa; Hisao Koriyama; Yuma Shiratori; Hajime Ito

doi:10.1021/acsorginorgau.2c00057

Copper(I)-Catalyzed Regio- and Stereoselective Silaboration of Terminal Allenes

ACS Org Inorg Au. 2023 Jan 4;3(2):104-108. doi: 10.1021/acsorginorgau.2c00057. eCollection 2023 Apr 5.

Authors

Yu Ozawa¹, Hisao Koriyama¹, Yuma Shiratori¹, Hajime Ito^{1

2}

Affiliations

¹ Division of Applied Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan.
² Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Sapporo, Hokkaido 060-8628, Japan.

Abstract

Organic compounds bearing both silyl and boryl groups are important building blocks in organic synthesis because of the adequate reactivity of the silyl and boryl groups and high stereospecificity in their derivatization reactions. The difference in reactivity between the silyl and boryl groups enables stepwise derivatization of these groups to afford complex molecules. Here, we report the copper(I)-catalyzed silaboration of terminal allenes to produce multisubstituted allylic boronates embedded with an alkenyl silane structure. The reaction can proceed with a variety of allenes and silylboranes. Furthermore, the silyl and boryl groups were successfully converted into other functional groups, while retaining the stereochemistry of the alkene moiety.