Regioselective Construction of Indolylated Cyclic Tetrasubstituted Carbon Centers through Brønsted Acid-Catalyzed Dearomative Skeletal Rearrangement of Azofurans

Yin Zhang, An-Qi Bao, Ming Wu, Qian Rao, Man-Su Tu,* Wen-Juan Hao,* Bo Jiang*

A Brønsted acid-catalyzed dearomative skeletal rearrangement of azofurans with indoles is reported, enabling a regioselective 1,6-addition, ring-opening and 1,4-addition cascade to produce 26 examples of indolylated pyrrol-2-ones with a cyclic tetrasubstituted stereocenter in good yields. This protocol demonstrates remarkable compatibility regarding azofurans and indoles with different substitution patterns, featuring complete regioselectivity, good functional group tolerance and mild conditions.

Adv. Synth. Catal. 2023, 365, 3718-3723; DOI: 10.1002/adsc.202300948