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Paper | Regular issue | Vol 104, No. 4, 2022, pp.764-775
Published online, 24th January, 2022
DOI: 10.3987/COM-21-14618
Rh(III)-Catalyzed Cascade C-H Activation/Annulation of Cyclic 2-Diazo-1,3-diketones with Benzoylacetonitriles to Polycyclic Benzo[de]chromenes

Lili Yuan, Lanlan Zhang, Youpeng Zuo, Guang Han, Xinwei He,* and Yongjia Shang*

*College of Chemistry and Materials Science, Anhui Normal University, No. 189 Jiuhua South Road, China

Abstract

The Rh(III)-catalyzed cascade C-H activation/benzannulation reactions of cyclic 2-diazo-1,3-diketones with benzoylacetonitriles leading to a simple and efficient strategy for the synthesis of polycyclic benzo[de]chromenes in good-to-high yields has been described. Four new bonds and two rings are generated through sequential C-H activation, carbenoid insertion, migratory insertion, and intramolecular annulation process in a single procedure. This protocol is features with readily available starting materials, favorable functional group compatibility, and high efficiency, atom- and step-economy.