Quantum Mechanical Prediction and Experimental Verification of Au(I)-Catalyzed Substitution-Controlled Syntheses of 1<i>H</i>-Pyrido[4,3-<i>b</i>]indole and Spiro[indoline-3,3′-pyridine] Derivatives

Abstract

Density functional theory calculations were applied to predict the pathways of gold(I)-catalyzed cycloisomerization of the indole substrates with 1,6-enynes, which were consistent with the ensuing experimental results. The substitution-controlled synthesis led to the formation of 1 H -pyrido[4,3- b ]indole and spiro[indoline-3,3′-pyridine] derivatives in a tunable way. The reactions had good functional group tolerances, and a possible mechanism was proposed based on the computational and experimental results.