Synthesis of Terminal Vinylindoles via RhIII -Catalyzed Direct C-H Alkenylation with Potassium Vinyltrifluoroborate

Chemistry. 2018 Apr 11;24(21):5469-5473. doi: 10.1002/chem.201706025. Epub 2018 Mar 23.

Abstract

An efficient RhIII -catalyzed direct C2-alkenylation of indoles using readily available potassium vinyltrifluoroborate under mild conditions has been developed. This protocol features wide substrate scope and excellent functional group compatibility, enabling a facile access to diverse terminal vinylindoles in moderate to good yields. Furthermore, the C2-alkenylated indole can be easily transformed into 9H-carbazole through a ring-closing metathesis/aromatization cascade.

Keywords: C−H alkenylation; heterocycles; indoles; rhodium; terminal vinylindole.