An efficient method for C7-position-selective alkenylation of N-substituted indolines with alkenes is reported. Various 7-alkenylindolines were obtained in moderate to excellent yields in air in the presence of catalytic amounts of [CpIrCl2]2, AgOTf, and Cu(OAc)2. The protocol relies on the use of a carbonyl or carbamoyl group on the nitrogen atom of indoline as a directing group and is potentially applicable to the synthesis of 7-alkenylindoles and 7-alkylindoles. Lettin the cat outta the bag: An efficient IrIII-catalyzed oxidative coupling of N-substituted indolines with various alkenes at the C7-position in air assisted by a carbonyl or carbamoyl group as a directing group is reported. The catalyst was prepared from [CpIrCl2]2 and AgOTf. A variety of 7-alkenylindolines were obtained in moderated to high yields. The reaction is potentially applicable to the synthesis of 7-alkylindoles and 7-alkenylindoles.
ASJC Scopus subject areas
- Organic Chemistry