Formation of C(sp2)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(sp²)Boronate Esters by Borylative Cyclization of Alkynes Using BCl₃

Andrew J. Warner, James R. Lawson, Valerio Fasano, Michael J. Ingleson^*

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

92 Citations (Scopus)

Abstract

BCl₃is an inexpensive electrophile which induces the borylative cyclization of a wide range of substituted alkynes to regioselectively form polycycles containing synthetically versatile C(sp²)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 BCl₃to generate trisubstituted vinyl boronate esters.

Original language	English
Pages (from-to)	11245-11249
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	54
Issue number	38
DOIs	https://doi.org/10.1002/anie.201505810
Publication status	Published - 1 Jan 2015

Keywords

alkynes
boron
cyclizations
heterocycles
synthetic methods

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abstract = "BCl3is an inexpensive electrophile which induces the borylative cyclization of a wide range of substituted alkynes to regioselectively form polycycles containing synthetically versatile C(sp2)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 BCl3to generate trisubstituted vinyl boronate esters.",

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KW - boron

KW - cyclizations

KW - heterocycles

KW - synthetic methods

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