Palladium-Catalyzed Reaction of 2-Alkynylanilines with 2-Vinylaziridines─Access to 3-Allylated Indoles

Xian Xiao; Zhong-Xia Wang

doi:10.1021/acs.joc.5c02278

Palladium-Catalyzed Reaction of 2-Alkynylanilines with 2-Vinylaziridines─Access to 3-Allylated Indoles

J Org Chem. 2025 Nov 21;90(46):16594-16606. doi: 10.1021/acs.joc.5c02278. Epub 2025 Nov 12.

Authors

Xian Xiao¹, Zhong-Xia Wang¹

Affiliation

¹ Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China.

PMID: 41222400
DOI: 10.1021/acs.joc.5c02278

Abstract

Reaction of 2-alkynylanilines with 2-vinylaziridines in dichloroethane in the presence of (CF₃COO)₂Pd (5 mol %), CF₃COONa (2.0 equiv), and N,N-diisopropylethylamine (0.5 equiv) at 80 °C for 12 h produces 3-allylated indoles in 26 to 97% yields with E-configurated C-C double bonds. This protocol is air compatible, applicable for a wide range of substrates and tolerates functional groups including OMe, F, Cl, CF₃, COOMe, NO₂, SiMe₃, and cyclopropyl groups.