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1,8-Addition/[3,3]-Rearrangement in the Functionalization of Unactivated Indole C(sp³)-H Bonds

Shao-Shuai Chen¹, Xue Huang¹, Zheng-Xian Peng¹

¹School of Pharmacy and Food Engineering, Wuyi University, Jiangmen, Guangdong 529020, China.

The Journal of Organic Chemistry

|March 27, 2026

Abstract:

We have developed a Brønsted acid-catalyzed 1,8-conjugate addition/[3,3]-rearrangement between propargylic p-QMs and 2,3-disubstituted indoles, achieving the direct functionalization of unactivated C(sp³)-H bonds of indoles. This method provides efficient access to a series of indole derivatives bearing an all-carbon quaternary center. The resulting indole products containing an alkynyl moiety can be readily transformed to indole-fused pyridine tricycles under gold catalysis, demonstrating the synthetic utility of this methodology. The mechanism of the reaction is proposed from several control experiments.

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