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

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...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2015-09, Vol.54 (38), p.11245-11249
Main Authors: Warner, Andrew J., Lawson, James R., Fasano, Valerio, Ingleson, Michael J.
Format: Article
Language:English
Subjects:
alkynes
boron
Communication
Communications
cyclizations
heterocycles
synthetic methods
Online Access:Get full text
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Summary: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. Alkyne+BCl3→Cyclization (A+B=C): BCl3 is a simple and inexpensive electrophile which induces a functional‐group‐tolerant borylative cyclization of aryl‐substituted alkynes and dialkynes. The reaction affords useful and regioselectively borylated polycycles.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201505810