Rhodium-Catalyzed Annulative Coupling Using Vinylene Carbonate as an Oxidizing Acetylene Surrogate

Transition-metal-catalyzed C–H activation and subsequent oxidative cyclization with alkynes has been a pow-erful tool for the synthesis of polycyclic aromatic compounds. Despite the substantial progress in this field, it is still a significant challenge to establish synthetic methodologies for the construction of non-substituted vinylene-fused aromatics. We herein report a Rh(III)-catalyzed C–H/N–H annulation with vinylene carbonate as an acetylene surrogate. Vinylene carbonate also acts as an internal oxidant to regenerate the Rh(III) species in situ; thus no external oxidant is required to trigger the oxidative annulation. This protocol is applicable to the direct synthesis of various N-heteroaromatics.Ghosh K., Nishii Y., Miura M.. Rhodium-Catalyzed Annulative Coupling Using Vinylene Carbonate as an Oxidizing Acetylene Surrogate. ACS Catalysis. 9(12), 11455-11460, (2019), 6 December 2019; ©2019 American Chemical Society. https://doi.org/10.1021/acscatal.9b04254