Regio- and Stereoselective Synthesis of Tetrasubstituted Alkenes via Ruthenium(II)-Catalyzed C-H Alkenylation/Directing Group Migration

Herein we report the regio- and stereoselective synthesis of tetrasubstituted alkenes from N-carbamoyl indoles and alkynes via ruthenium(II)-catalyzed C-H alkenylation/directing group migration, in which the carbamoyl directing group is endowed with a dual role of auxiliary group and migrating acylation reagent via C-N bond cleavage. This method features broad substrate scope, high atom- and step-economy, good functional group tolerance and mild redox-neutral conditions at room temperature. A series of structurally diverse tetrasubstituted alkenes were synthesized in good to excellent yields, highlighting the efficiency of this method.

Automated summary

We report the regio- and stereoselective synthesis of tetrasubstituted alkenes using N-carbamoyl indoles and alkynes via ruthenium(II)-catalyzed C-H alkenylation/directing group migration. The carbamoyl directing group serves as both an auxiliary group and migrating acylation reagent through C-N bond cleavage. This method shows broad substrate scope, high atom and step economy, good functional group tolerance, and mild conditions at room temperature, allowing for the efficient synthesis of structurally diverse tetrasubstituted alkenes.