Synthesis of Multisubstituted Benzenes from Phenols via Multisubstituted Benzynes

Abstract

A new method to synthesize multifunctionalized arenes from simple phenols through aryne intermediates is described. Multisubstituted aryne precursors were prepared from phenols by Ir-catalyzed C–H borylation, deborylthiolation, O-triflylation, S-oxidation, and further modification through ortho-deprotonation directed by the sulfoxide moiety. Various multisubstituted arenes were synthesized by transformations of highly functionalized aryne intermediates generated from the o-sulfinylaryl triflates.

Key words

aryne intermediates - sulfoxides - Knochel–Hauser base - Grignard reagents - triazoles

Publication History

Received: 17 March 2022

Accepted after revision: 25 April 2022

Accepted Manuscript online:
25 April 2022

Article published online:
09 June 2022

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