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meso-Tetraphenylporphyrin Iron Chloride Catalyzed Selective Oxidative Cross-Coupling of Phenols

Hadas Shalit, Anna Libman, Doron Pappo

J Am Chem Soc. 2017 Sep 27;139(38):13404-13413.

PMID: 28862442

Abstract:

A novel catalytic system for oxidative cross-coupling of readily oxidized phenols with poor nucleophilic phenolic partners based on an iron meso-tetraphenylporphyrin chloride (Fe[TPP]Cl) complex in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) was developed. The unique chemoselectivity of this reaction is attributed to the coupling between a liberated phenoxyl radical with an iron-ligated phenolic coupling partner. The conditions are scalable for preparing a long list of unsymmetrical biphenols assembled from a less reactive phenolic unit substituted with alkyl or halide groups.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP917237-A meso-Tetraphenylporphyrin meso-Tetraphenylporphyrin 917-23-7 Price
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