Rhodium-Catalyzed Dealkenylative Arylation of Alkenes with Arylboronic Compounds

Tan, G.; Das, M.; Maisuls, I.; Strassert, C. A.; Glorius, F.

Abstract

Abstract The C?C bond formation reaction represents a fundamental and important transformation in synthetic chemistry, and exploring new types of C?C bond formation reactions is recognized as appealing, yet challenging. Herein, we disclose the first example of rhodium-catalyzed dealkenylative arylation of alkenes with arylboronic compounds, thereby providing an unconventional access to bi(hetero)aryls with excellent chemoselectivity. In this method, C(aryl)?C(alkenyl) and C(alkenyl)?C(alkenyl) bonds in various alkenes and 1,3-dienes can be cleaved via a hydrometalation and followed by ?-carbon elimination pathway for Suzuki?Miyaura reactions. Furthermore, a series of novel organic fluorescent molecules with excellent photophysical properties has been efficiently constructed with this protocol.