Process for the synthesis of phenols from arenes

US6828466B2 · kind B2 · utility

Assignee

• BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITY · US

Inventors

• Robert E. Maleczka · Lansing, US
• Milton R. Smith, III · East Lansing, US
• Daniel Holmes · Lansing, US
• Feng Shi · Beijing, CN

Key dates

• Filing date: Jul 15, 2003
• Grant date: Dec 7, 2004
• Expiry date: Oct 10, 2023

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C213/00
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A process to synthesize substituted phenols such as those of the general formula RR′R″Ar(OH) wherein R, R′, and R″ are each independently hydrogen or any group which does not interfere in the process for synthesizing the substituted phenol including, but not limited to, halo, alkyl, alkoxy, carboxylic ester, amine, amide; and Ar is any variety of aryl or hetroaryl by means of oxidation of substituted arylboronic esters is described. In particular, a metal-catalyzed C—H activation/borylation reaction is described, which when followed by direct oxidation in a single or separate reaction vessel affords phenols without the need for any intermediate manipulations. More particularly, a process wherein Ir-catalyzed borylation of arenes using pinacolborane (HBPin) followed by oxidation of the intermediate arylboronic ester by OXONE is described.