Substrate-Assisted, Transition-Metal-Free Diboration of Alkynamides with Mixed Diboron: Regio- and Stereoselective Access to trans-1,2-Vinyldiboronates

Astha Verma; Russell F Snead; Yumin Dai; Carla Slebodnick; Yinuo Yang; Haizhu Yu; Fu Yao; Webster L Santos

doi:10.1002/anie.201700946

Substrate-Assisted, Transition-Metal-Free Diboration of Alkynamides with Mixed Diboron: Regio- and Stereoselective Access to trans-1,2-Vinyldiboronates

Angew Chem Int Ed Engl. 2017 Apr 24;56(18):5111-5115. doi: 10.1002/anie.201700946. Epub 2017 Mar 29.

Authors

Astha Verma¹, Russell F Snead¹, Yumin Dai¹, Carla Slebodnick¹, Yinuo Yang², Haizhu Yu², Fu Yao³, Webster L Santos¹

Affiliations

¹ Department of Chemistry, Virginia Tech, 900 West Campus Drive, Blacksburg, VA, 24061, USA.
² Department of Chemistry and Center for Atomic Engineering of Advanced Materials, Anhui University, Hefei, Anhui, 230601, P.R. China.
³ Department of Chemistry and Materials Science, University of Science and Technology of China, Hefei, Anhui, 230026, P.R. China.

PMID: 28371182
DOI: 10.1002/anie.201700946

Abstract

A substrate-assisted diboration of alkynamides using the unsymmetrical pinacolato-1,8-diaminonaphthalenato diboron (pinBBdan) is described. The transition-metal-free reaction proceeds in a regio- and stereoselective fashion to exclusively afford trans-vinyldiboronates in good to excellent yields. Notably, Bdan and Bpin are installed on the α- and β-carbon atoms, respectively.

Keywords: alkenes; boron; chemoselectivity; cross-coupling; synthetic methods.

Publication types

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