Synthesis of 1,1,1-Tris(boronates) from Vinylarenes by Co-Catalyzed Dehydrogenative Borylations-Hydroboration

Lei Zhang; Zheng Huang

doi:10.1021/jacs.5b11366

Synthesis of 1,1,1-Tris(boronates) from Vinylarenes by Co-Catalyzed Dehydrogenative Borylations-Hydroboration

J Am Chem Soc. 2015 Dec 23;137(50):15600-3. doi: 10.1021/jacs.5b11366. Epub 2015 Dec 10.

Authors

Lei Zhang¹, Zheng Huang¹

Affiliation

¹ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry , 345 Lingling Road, Shanghai 200032, China.

PMID: 26651355
DOI: 10.1021/jacs.5b11366

Abstract

The selective preparation of 1,1,1-tris(boronates) from vinylarenes and bis(pinacolato)diboron is described. The reactions occur at ambient temperature with excellent selectivity, high yields, and good functional group tolerance. Mechanistic studies suggest that Co(I)-catalyzed double dehydrogenative borylations generate a 1,1-diborylalkene intermediate, which undergoes hydroboration with pinacolborane formed in situ to yield 1,1,1-tris(boronate).

Publication types

Research Support, Non-U.S. Gov't