Hydrogen Peroxide/Boric Acid: An Efficient System for Oxidation of Aromatic Aldehydes and Ketones to Phenols

Abstract

and-conditions-of-access.pdf This article may be used for research, teaching and private study purposes. Any substantial or systematic reproduction, redistribution , reselling , loan or sub-licensing, systematic supply or distribution in any form to anyone is expressly forbidden. The publisher does not give any warranty express or implied or make any representation that the contents will be complete or accurate or up to date. The accuracy of any instructions, formulae and drug doses should be independently verified with primary sources. The publisher shall not be liable for any loss, actions, claims, proceedings, demand or costs or damages whatsoever or howsoever caused arising directly or indirectly in connection with or arising out of the use of this material.

Evolution of an oxidative dearomatization enabled total synthesis of vinigrol

“…We chose a trifluoroethyl group for this purpose ( 75 ). Dakin oxidation of 75 proceeded fantastically well when boronic acid 26 was used as an additive ( 76 ). The proposed oxidative dearomatization/Diels-Alder cycloaddition cascade proceeded favorably to form desired product 77 using trifluoroethyl ether as a deactivating group.…”

Oxidation of aromatic aldehydes and ketones by H2O2/CH3ReO3 in ionic liquids: a catalytic efficient reaction to achieve dihydric phenols

“…9 However, under these conditions, reactions were too slow to be commercially attractive. Hydrogen peroxide/boric acid, 10 hydrogen peroxide/selenium compounds, 11 sodium perborate and sodium percarbonate, 12 m-chloroperbenzoic acid 13 were other useful reagents to convert aromatic aldehydes to the corresponding phenols, but these procedures required long reactions time, in some cases up to 30 h. Recently, Sn-Beta zeolites were used to activate hydrogen peroxide 14 providing an interesting example of good reactivity of aromatic aldehydes in short reaction times.…”

Boric Acid as Highly Efficient Catalyst for the Synthesis of Phenols from Arylboronic Acids

“…A probable mechanistic pathway has been proposed for the ipso ‐hydroxylation of arylboronic acids (Scheme ) following the literature report . Hydrogen peroxide in presence of boric acid is a known system for oxidation reactions .…”