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Gold(III)-Catalyzed Decarboxylative C3-Benzylation of Indole-3-carboxylic Acids with Benzylic Alcohols in Water

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journal contribution
posted on 23.01.2019, 00:00 by Hidemasa Hikawa, Fumiya Kotaki, Shoko Kikkawa, Isao Azumaya
A strategy for the gold­(III)-catalyzed decarboxylative coupling reaction of indole-3-carboxylic acids with benzylic alcohols has been developed. This cascade reaction is devised as a straightforward and efficient synthetic route for 3-benzylindoles in moderate to excellent yields (50–93%). A Hammett study of the protodecarboxylation gives a negative ρ value, suggesting that there is a buildup of positive charge on the indole ring in the transition state. Furthermore, comparison of initial rates in H2O and in D2O reveals an observed kinetic solvent isotope effect (KSIE = 2.7). This simple protocol, which affords the desired products with CO2 and water as the coproducts, can be achieved under mild conditions without the need for base or other additives in water.