Rhodium(III)-Catalyzed Sequential Cyclization of N-Boc Hydrazones with Propargylic Monofluoroalkynes via C-H Activation/C-F Cleavage for the Synthesis of Spiro[cyclobutane-1,9'-indeno[1,2-a]indenes].

Cheng Deng, Lu Jiang, Jinzhong Yao, Qian Liang, Lin Miao, Changchang Li, Maozhong Miao, Hongwei Zhou

The Journal of organic chemistry 2022 May 06

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An effective rhodium(III) catalysis for the construction of valuable tetracyclic compounds is described herein. This domino process involving the C-H activation/[3 + 2] annulation/intramolecular Friedel-Crafts reaction sequences of simple and readily available N-Boc hydrazones and propargylic monofluoroalkynes afforded fused tetracyclic spiro[cyclobutane-1,9'-indeno[1,2-a]indenes] in moderate to good yields, featuring three C-C bond formation. Moreover, control experiments indicated that the C-H activation might be involved in the rate-determining step.

Citation

Cheng Deng, Lu Jiang, Jinzhong Yao, Qian Liang, Lin Miao, Changchang Li, Maozhong Miao, Hongwei Zhou. Rhodium(III)-Catalyzed Sequential Cyclization of N-Boc Hydrazones with Propargylic Monofluoroalkynes via C-H Activation/C-F Cleavage for the Synthesis of Spiro[cyclobutane-1,9'-indeno[1,2-a]indenes]. The Journal of organic chemistry. 2022 May 06;87(9):6105-6114