Synthesis of pyrrolo[2,1,5-cd]indolizines through dehydrogenative Heck annelation of indolizines with diaryl acetylenes using dioxygen as an oxidant

Huayou Hu; Guodong Li; Weiming Hu; Yun Liu; Xiang Wang; Yuhe Kan; Min Ji

doi:10.1021/ol503681n

Synthesis of pyrrolo[2,1,5-cd]indolizines through dehydrogenative Heck annelation of indolizines with diaryl acetylenes using dioxygen as an oxidant

Org Lett. 2015 Mar 6;17(5):1114-7. doi: 10.1021/ol503681n. Epub 2015 Feb 20.

Authors

Huayou Hu¹, Guodong Li, Weiming Hu, Yun Liu, Xiang Wang, Yuhe Kan, Min Ji

Affiliation

¹ Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University , Huaian 223300, China.

PMID: 25699418
DOI: 10.1021/ol503681n

Abstract

A dehydrogenative Heck annelation reaction of indolizine with diaryl acetylene via dual C-H bond cleavage was developed. Oxygen gas was employed as a clean oxidant in this catalysis under base-free conditions. Diarylpyrrolo[2,1,5-cd]indolizines were synthesized with high atom economy. In addition, kinetic isotope experiments provided evidence for C-H bond metalation of the 5-position of the indolizine as the rate-limiting step.

Publication types

Research Support, Non-U.S. Gov't