Divergent reaction pathways for phenol arylation by arynes: synthesis of helicenes and 2-arylphenols?

Chemical Science Pub Date: 2012-10-18 DOI: 10.1039/C2SC21288A

Abstract

Two reactions of phenols with arynes have been developed. If LiTMP base is employed, arynes generated from aryl chlorides react with phenols to form helicenes. o-Arylation of phenols can be achieved by employing tBuONa base in the presence of AgOAc. Direct arylation of binol was achieved leading to the shortest pathway to o,o′-diarylbinols.

Graphical abstract: Divergent reaction pathways for phenol arylation by arynes: synthesis of helicenes and 2-arylphenols
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