A Concise Route to Keto-Bridged Polyphenols by Photo-Fries Rearrangement in Flow

Xin-Jie Lin; Chien-Lung Wang; Chi-How Peng; Hsueh-Ju Liu; Yen-Ku Wu

doi:10.1002/asia.202400269

A Concise Route to Keto-Bridged Polyphenols by Photo-Fries Rearrangement in Flow

Chem Asian J. 2024 Jul 2;19(13):e202400269. doi: 10.1002/asia.202400269. Epub 2024 May 28.

Authors

Xin-Jie Lin¹, Chien-Lung Wang², Chi-How Peng², Hsueh-Ju Liu¹, Yen-Ku Wu¹

Affiliations

¹ Department of Applied Chemistry, National Yang Ming Chiao Tung University, No. 1001 University Road, Hsinchu, 30010, Taiwan.
² Department of Chemistry, National Taiwan University, No. 1, Sec. 4, Roosevelt Rd., Taipei, 10617, Taiwan.

PMID: 38619083
DOI: 10.1002/asia.202400269

Abstract

Described is a new synthetic route to bis(2-hydroxy-3,5-di-t-butylphenyl)methanone and its derivatives. The combined esterification/photo-Fries rearrangement approach enables a modular preparation of keto-bridged polyphenols. This protecting group-free process is highly atom- and step-economic, and a scalable production was easily achieved in the continuous-flow mode.

Keywords: hydroxybenzophenone; oxygen donor ligand; phenol; photo-Fries rearrangement; photoflow synthesis.

Abstract

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