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Direct C-Arylation of Free (NH)-Indoles and Pyrroles Catalyzed by Ar−Rh(III) Complexes Assembled In Situ

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journal contribution
posted on 13.04.2005, 00:00 authored by Xiang Wang, Benjamin S. Lane, Dalibor Sames
Ar−Rh(III) pivalate complexes assembled in situ from the reaction of [RhCl(coe)2]2 (coe = cis-cyclooctene), [p-(CF3)C6H4]3P, and CsOPiv effectively catalyzed the direct C-arylation of free (NH)-indoles and (NH)-pyrroles in good yields and with high regioselectivity. The reaction displayed excellent functional group compatibility and low moisture sensitivity. Kinetics studies support a mechanism involving phosphine displacement by indole in complex 2 (resting state of the catalyst), followed by a rate-limiting C−H bond metalation.