Pinacol boronates by direct arene borylation with borenium cations

Alessandro Del Grosso; Paul J. Singleton; Christopher A. Muryn; Michael J. Ingleson

doi:10.1002/anie.201006196

Pinacol boronates by direct arene borylation with borenium cations

Alessandro Del Grosso, Paul J. Singleton, Christopher A. Muryn, Michael J. Ingleson

School of Chemistry

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

Abstract

Borenium does it direct: A boron analogue of the Friedel-Crafts reaction uses inexpensive catecholatoborenium cations that are sufficiently electrophilic to borylate arenes by electrophilic aromatic substitution. The direct arene borylation proceeds with high regioselectivity for a range of anilines, N-heterocycles, and thiophenes. Subsequent one-pot transesterification provides the synthetically useful pinacol boronate esters (see scheme).

Original language	English
Pages (from-to)	2102-2106
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	9
DOIs	https://doi.org/10.1002/anie.201006196
Publication status	Published - 25 Feb 2011

Keywords

borenium ions
borocations
boronate esters
borylation
electrophilic substitution

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10.1002/anie.201006196

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title = "Pinacol boronates by direct arene borylation with borenium cations",

abstract = "Borenium does it direct: A boron analogue of the Friedel-Crafts reaction uses inexpensive catecholatoborenium cations that are sufficiently electrophilic to borylate arenes by electrophilic aromatic substitution. The direct arene borylation proceeds with high regioselectivity for a range of anilines, N-heterocycles, and thiophenes. Subsequent one-pot transesterification provides the synthetically useful pinacol boronate esters (see scheme).",

keywords = "borenium ions, borocations, boronate esters, borylation, electrophilic substitution",

author = "{Del Grosso}, Alessandro and Singleton, {Paul J.} and Muryn, {Christopher A.} and Ingleson, {Michael J.}",

year = "2011",

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doi = "10.1002/anie.201006196",

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T1 - Pinacol boronates by direct arene borylation with borenium cations

AU - Del Grosso, Alessandro

AU - Singleton, Paul J.

AU - Muryn, Christopher A.

AU - Ingleson, Michael J.

PY - 2011/2/25

Y1 - 2011/2/25

N2 - Borenium does it direct: A boron analogue of the Friedel-Crafts reaction uses inexpensive catecholatoborenium cations that are sufficiently electrophilic to borylate arenes by electrophilic aromatic substitution. The direct arene borylation proceeds with high regioselectivity for a range of anilines, N-heterocycles, and thiophenes. Subsequent one-pot transesterification provides the synthetically useful pinacol boronate esters (see scheme).

AB - Borenium does it direct: A boron analogue of the Friedel-Crafts reaction uses inexpensive catecholatoborenium cations that are sufficiently electrophilic to borylate arenes by electrophilic aromatic substitution. The direct arene borylation proceeds with high regioselectivity for a range of anilines, N-heterocycles, and thiophenes. Subsequent one-pot transesterification provides the synthetically useful pinacol boronate esters (see scheme).

KW - borenium ions

KW - borocations

KW - boronate esters

KW - borylation

KW - electrophilic substitution

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JO - Angewandte Chemie International Edition

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