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Issue 28, 2016
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Regioselective routes to orthogonally-substituted aromatic MIDA boronates

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Abstract

A series of tetrasubstituted aromatics has been synthesized, many of which are based on elaborated N-methyliminodiacetic acid (MIDA)-boronates. A sequence employing nitration, bromination, stepwise Suzuki–Miyaura (SM) coupling with a boronic acid, then base-mediated unmasking of the boronic acid from the MIDA-boronate and a second SM-coupling has led to our desired, mainly 1,2,4,5-substituted tetrasubstituted aromatic targets.

Graphical abstract: Regioselective routes to orthogonally-substituted aromatic MIDA boronates

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Article information


Submitted
25 May 2016
Accepted
14 Jun 2016
First published
14 Jun 2016

This article is Open Access

Org. Biomol. Chem., 2016,14, 6751-6756
Article type
Paper

Regioselective routes to orthogonally-substituted aromatic MIDA boronates

A. J. Close, P. Kemmitt, S. Mark Roe and J. Spencer, Org. Biomol. Chem., 2016, 14, 6751
DOI: 10.1039/C6OB01141A

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