Formation of C(sp(2))-boronate esters by borylative cyclization of alkynes using BCl3

Andrew J Warner; James R Lawson; Valerio Fasano; Michael J Ingleson

doi:10.1002/anie.201505810

Formation of C(sp(2))-boronate esters by borylative cyclization of alkynes using BCl3

Angew Chem Int Ed Engl. 2015 Sep 14;54(38):11245-9. doi: 10.1002/anie.201505810. Epub 2015 Jul 31.

Authors

Andrew J Warner¹, James R Lawson¹, Valerio Fasano¹, Michael J Ingleson²

Affiliations

¹ School of Chemistry, University of Manchester, Manchester, M13 9PL (UK).
² School of Chemistry, University of Manchester, Manchester, M13 9PL (UK). Michael.ingleson@manchester.ac.uk.

Abstract

BCl3 is an inexpensive electrophile which induces the borylative cyclization of a wide range of substituted alkynes to regioselectively form polycycles containing synthetically versatile C(sp(2) )boronate esters. It proceeds rapidly, with good yields and is compatible with a range of functional groups and substitution patterns. Intermolecular 1,2-carboboration of alkynes is also achieved using BCl3 to generate trisubstituted vinyl boronate esters.

Keywords: alkynes; boron; cyclizations; heterocycles; synthetic methods.