Cascade bicyclizations of o-alkynyl aldehydes with thiazolium salts: a new access toward poly-functionalized indeno[2,1-b]pyrroles.

A new cascade bicyclization of o-alkynyl aldehydes with thiazolium salts is described, in which 25 examples of densely functionalized indeno[2,1-b]pyrroles are achieved in a functional-group-compatible manner. Thiazole carbenes generated in situ from thiazolium salts play dual roles as reaction partners and as NHC catalysts. The synthetic utility of these bicyclization reactions results in subsequent C-C bond-forming events to rapidly build up molecular complexity.