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

98 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

Access to Document

10.1002/anie.201505810

Handle.net

Persistent link

Cite this

@article{fe758b1c5e48494294980fd4e6705f1a,

title = "Formation of C(sp2)Boronate Esters by Borylative Cyclization of Alkynes Using BCl3",

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.",

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

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

year = "2015",

month = jan,

day = "1",

doi = "10.1002/anie.201505810",

language = "English",

volume = "54",

pages = "11245--11249",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley \& Sons, Ltd.",

number = "38",

}

TY - JOUR

T1 - Formation of C(sp2)Boronate Esters by Borylative Cyclization of Alkynes Using BCl3

AU - Warner, Andrew J.

AU - Lawson, James R.

AU - Fasano, Valerio

AU - Ingleson, Michael J.

PY - 2015/1/1

Y1 - 2015/1/1

N2 - 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.

AB - 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.

KW - alkynes

KW - boron

KW - cyclizations

KW - heterocycles

KW - synthetic methods

UR - https://www.scopus.com/pages/publications/84950328483

U2 - 10.1002/anie.201505810

DO - 10.1002/anie.201505810

M3 - Article (Academic Journal)

C2 - 26237115

AN - SCOPUS:84950328483

SN - 1433-7851

VL - 54

SP - 11245

EP - 11249

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 38

ER -