Leveraging the Persistent Radical Effect in the Synthesis of Trans-2,3-Diaryl Dihydrobenzofurans

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2023 Jun 30

PMID 37390358

Authors

Bec J Roldan

Travis A Hammerstad

Matthew S Galliher

Mitchell H Keylor

Derek A Pratt

Corey R J Stephenson

Affiliations

Soon will be listed here.

Abstract

A simple method for accessing trans-2,3-diaryl dihydrobenzofurans is reported. This approach leverages the equilibrium between quinone methide dimers and their persistent radicals. This equilibrium is disrupted by phenols that yield comparatively transient phenoxyl radicals, leading to cross-coupling between the persistent and transient radicals. The resultant quinone methides with pendant phenols rapidly cyclize to form dihydrobenzofurans (DHBs). This putative biomimetic access to dihydrobenzofurans provides superb functional group tolerance and a unified approach for the synthesis of resveratrol-based natural products.

Citing Articles

Novel transition metal-free synthetic protocols toward the construction of 2,3-dihydrobenzofurans: a recent update.

Mushtaq A, Irfan M, Haq A, Mansha A, Khan S, Zahoor A Front Chem. 2024; 12:1470861.

PMID: 39734577 PMC: 11672212. DOI: 10.3389/fchem.2024.1470861.

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