Palladium-Catalyzed Dearomative Heck/C(sp)-H Activation/Decarboxylative Cyclization of C2-Tethered Indoles.

Until now, palladium-catalyzed dearomative Heck reactions of indoles were largely limited to β-H elimination and nucleophilic capture of the transient alkyl-Pd(II) species. Herein, we disclose a novel palladium-catalyzed dearomative Heck/C(sp)-H activation/decarboxylative cyclization of C2-tethered indoles. In this protocol, the alkyl-Pd(II) species formed by dearomatization of C2-tethered indoles is not terminated by common β-H elimination or nucleophilic capture, but rather generates ,-palladacycle via C-H activation.