Rh-Catalyzed Formal [3 + 2] Cycloaddition Reactions with Cyclopropenones via Sequential C-H/C-C Bond Activation
Qing-Long Qu1, Yu-Tong Ren1, Jun-Tao Cao1
1Key Laboratory of Synthetic and Natural Functional Molecule of Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an 710127, China.
Abstract:
The utilization of high-valent metal catalysts to promote cycloaddition reactions involving π bonds through C-C bond activation remains challenging. Despite extensive research, the cycloaddition of aldehydes with cyclopropenones catalyzed by metal complexes has not been documented. Herein, we disclose a novel Rh(III)-catalyzed cycloaddition reaction between cyclopropenones and aldehydes, enabling the efficient synthesis of highly functionalized furanones. A detailed mechanistic investigation was conducted, revealing the likely involvement of a tripodal Rh-carbene intermediate in the catalytic cycle, which facilitates the product release pathway. This reaction exhibits a broad substrate scope, good functional group compatibility, and high atom economy, thereby offering a versatile and general approach to the construction of furanones.
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