Organic Chemistry Laboratory, Nagoya University

Kazuhiro Hata, Yasutomo Segawa, and Kenichiro Itami

Chem. Commun. 2012, Accepted Manuscript. DOI: 10.1039/C2CC33184E

We herein report a base-promoted generation of sterically hindered 1,3,5-triaryl 2-pyridylidene from the corresponding pyridinium salt. The thus-generated 2-pyridylidene was trapped by S8 and Me2SAuCl to form 2-pyridinethione and a 2-pyridylidene-gold(I) complex, respectively. Rearrangement of pyridylidene to pyrido[1,2-a]indole indicates high reactivity of the carbene center of 2-pyridylidene.