Rh(II)-catalyzed Denitrogenative Cascade of 1,2,3-Triazolyl Propiolates and Indoles: Access to Butenolide Tethered Homotryptamines.

Abstract

An efficient Rh(II)-catalyzed denitrogenative reaction of indoles with 1,2,3-triazolyl propiolates has been developed. This methodology provides facile access to butenolide tethered homotryptamines in good to excellent yields under operationally simple conditions and features a broad substrate scope. Overall, the reaction sequence involves the formation of three new bonds (two C-C and one C-O) in a nucleophilic cascade manner. Additionally, an intramolecular rearrangement of these derivatives to thermodynamically more stable butenolides is also demonstrated.