Access to Stereodefined (E)-2-Silylallylboronates via Regioselective Chloroboration of Allenylsilanes

Zhantao Yang; Tingjie Liu; Xixi Chen; Ranran Wan; Yang Li; Xianzhen Wang; Chun-Hua Yang; Junbiao Chang

doi:10.1021/acs.orglett.9b03720

Access to Stereodefined (E)-2-Silylallylboronates via Regioselective Chloroboration of Allenylsilanes

Org Lett. 2019 Dec 6;21(23):9541-9544. doi: 10.1021/acs.orglett.9b03720. Epub 2019 Nov 12.

Authors

Zhantao Yang^{1

2}, Tingjie Liu¹, Xixi Chen¹, Ranran Wan¹, Yang Li¹, Xianzhen Wang¹, Chun-Hua Yang¹, Junbiao Chang²

Affiliations

¹ Henan Key Laboratory of New Optoelectronic Functional Materials, College of Chemistry and Chemical Engineering , Anyang Normal University , 436 Xian'ge Road , Anyang 455000 , P. R. China.
² School of Pharmaceutical Sciences , Zhengzhou University , Zhengzhou , Henan 450001 , P. R. China.

PMID: 31713429
DOI: 10.1021/acs.orglett.9b03720

Abstract

A catalyst-free method for the highly regioselective chloroboration of allenylsilanes is described. In the presence of BCl₃ and 2,6-lutidine, chloroboration of allenylsilanes proceeds smoothly without any catalyst, and the product could be treated with pinacol to afford the corresponding pinacol borates in one-pot reaction. This reaction provides a direct approach to construct valuable 2-silylallylboronate frameworks with operational simplicity and high atom-economy.