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

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

Research output: Contribution to journal › Article › peer-review

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(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 BCl3 to 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 https://doi.org/10.1002/anie.201505810
Publication status	Published - 14 Sept 2015

Keywords

alkynes
boron
cyclizations
heterocycles
synthetic methods

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title = "Formation of C(sp(2))-Boronate Esters by Borylative Cyclization of Alkynes Using BCl3",

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(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 BCl3 to generate trisubstituted vinyl boronate esters.",

keywords = "alkynes, boron, cyclizations, heterocycles, synthetic methods",

author = "Warner, \{Andrew J.\} and Lawson, \{James R.\} and Valerio Fasano and Ingleson, \{Michael J.\}",

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AU - Warner, Andrew J.

AU - Lawson, James R.

AU - Fasano, Valerio

AU - Ingleson, Michael J.

N1 - Times Cited: 0

PY - 2015/9/14

Y1 - 2015/9/14

N2 - 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(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 BCl3 to generate trisubstituted vinyl boronate esters.

AB - 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(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 BCl3 to generate trisubstituted vinyl boronate esters.

KW - alkynes

KW - boron

KW - cyclizations

KW - heterocycles

KW - synthetic methods

U2 - 10.1002/anie.201505810

DO - 10.1002/anie.201505810

M3 - Article

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JO - ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

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IS - 38

ER -

Formation of C(sp(2))-Boronate Esters by Borylative Cyclization of Alkynes Using BCl3

Abstract

Keywords

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