A modular synthesis of functionalised phenols enabled by controlled boron speciation

John J. Molloy; Robert P. Law; James W.B. Fyfe; Ciaran P. Seath; David J. Hirst; Allan J.B. Watson

doi:10.1039/C5OB00078E

A modular synthesis of functionalised phenols enabled by controlled boron speciation

John J. Molloy, Robert P. Law, James W.B. Fyfe, Ciaran P. Seath, David J. Hirst, Allan J.B. Watson

Pure And Applied Chemistry

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Abstract

A modular synthesis of functionalised biaryl phenols from two boronic acid derivatives has been developed via one-pot Suzuki-Miyaura cross-coupling, chemoselective control of boron solution speciation to generate a reactive boronic ester in situ, and oxidation. The utility of this method has been further demonstrated by application in the synthesis of drug molecules and components of organic electronics, as well as within iterative cross-coupling.

Original language	English
Number of pages	10
Journal	Organic and Biomolecular Chemistry
Early online date	21 Jan 2015
DOIs	https://doi.org/10.1039/C5OB00078E
Publication status	E-pub ahead of print - 21 Jan 2015

Keywords

boronic acid
chemoselective control
boron
phenols

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10.1039/C5OB00078E

Molloy-etal-OBC-2015-A-modular-synthesis-of-functionalised-phenolsAccepted author manuscript, 571 KB

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abstract = "A modular synthesis of functionalised biaryl phenols from two boronic acid derivatives has been developed via one-pot Suzuki-Miyaura cross-coupling, chemoselective control of boron solution speciation to generate a reactive boronic ester in situ, and oxidation. The utility of this method has been further demonstrated by application in the synthesis of drug molecules and components of organic electronics, as well as within iterative cross-coupling.",

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AU - Molloy, John J.

AU - Law, Robert P.

AU - Fyfe, James W.B.

AU - Seath, Ciaran P.

AU - Hirst, David J.

AU - Watson, Allan J.B.

PY - 2015/1/21

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N2 - A modular synthesis of functionalised biaryl phenols from two boronic acid derivatives has been developed via one-pot Suzuki-Miyaura cross-coupling, chemoselective control of boron solution speciation to generate a reactive boronic ester in situ, and oxidation. The utility of this method has been further demonstrated by application in the synthesis of drug molecules and components of organic electronics, as well as within iterative cross-coupling.

AB - A modular synthesis of functionalised biaryl phenols from two boronic acid derivatives has been developed via one-pot Suzuki-Miyaura cross-coupling, chemoselective control of boron solution speciation to generate a reactive boronic ester in situ, and oxidation. The utility of this method has been further demonstrated by application in the synthesis of drug molecules and components of organic electronics, as well as within iterative cross-coupling.

KW - boronic acid

KW - chemoselective control

KW - boron

KW - phenols

U2 - 10.1039/C5OB00078E

DO - 10.1039/C5OB00078E

M3 - Article

SN - 1477-0520

JO - Organic and Biomolecular Chemistry

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A modular synthesis of functionalised phenols enabled by controlled boron speciation

Abstract

Keywords

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