Decarboxylative Suzuki-Miyaura coupling of (hetero)aromatic carboxylic acids using iodine as the terminal oxidant

Quibell, Jacob M., Duan, Guojian, Perry, Gregory J.P. and Larrosa, Igor (2019) Decarboxylative Suzuki-Miyaura coupling of (hetero)aromatic carboxylic acids using iodine as the terminal oxidant. Chemical Communications, 55 (45), 6445-6448. (doi:10.1039/c9cc01817d).

Record type: Article

Abstract

A novel methodology for the decarboxylative Suzuki-Miyaura-type coupling has been established. This process uses iodine or a bromine source as both the decarboxylation mediator and the terminal oxidant, thus avoiding the need for stoichiometric amounts of transition metal salts previously required. Our new protocol allows for the construction of valuable biaryl architectures through the coupling of (hetero)aromatic carboxylic acids with arylboronic acids. The scope of this decarboxylative Suzuki reaction has been greatly diversified, allowing for previously inaccessible non-ortho-substituted aromatic acids to undergo this transformation. The procedure also benefits from low catalyst loadings and the absence of stoichiometric transition metal additives.

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Published date: 2019

Additional Information: Funding Information: We gratefully acknowledge the University of Manchester School of Chemistry for funding (to G. J. P. P.). We also thank the National Natural Science Foundation of China (No. 21762001) and the China Scholarship Council for a visiting scholarship (to G. D.). Publisher Copyright: © 2019 The Royal Society of Chemistry.