Angewandte Chemie. International edition in English 2015-05-04

Rhodium(I)-catalyzed regiospecific dimerization of aromatic acids: two direct ch bond activations in water.

Hang Gong, Huiying Zeng, Feng Zhou, Chao-Jun Li

Index: Angew. Chem. Int. Ed. Engl. 54 , 5718-21, (2015)

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Abstract

2,2'-Diaryl acids are key building blocks for some of the most important and high-performance polymers such as polyesters and polyamides (imides), as well as structural motifs of MOFs (metal-organic frameworks) and biological compounds. In this study, a direct, regiospecific and practical dimerization of simple aromatic acids to generate 2,2'-diaryl acids has been discovered, which proceeds through two rhodium-catalyzed CH activations in water. This reaction can be easily scaled up to gram level by using only 0.4-0.6 mol % of the rhodium catalyst. As a proof-of-concept, the natural product ellagic acid was synthesized in two steps by this method. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.