Catalytic 4-exo-dig carbocyclization for the construction of furan-fused cyclobutanones and synthetic applications

Kemiao Hong, Yi Zhou, Haoxuan Yuan, Zhijing Zhang, Jingjing Huang, Shanliang Dong, Wenhao Hu, Zhi-Xiang Yu () and Xinfang Xu ()
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Kemiao Hong: Sun Yat-sen University
Yi Zhou: Peking University
Haoxuan Yuan: Sun Yat-sen University
Zhijing Zhang: Sun Yat-sen University
Jingjing Huang: Sun Yat-sen University
Shanliang Dong: Sun Yat-sen University
Wenhao Hu: Sun Yat-sen University
Zhi-Xiang Yu: Peking University
Xinfang Xu: Sun Yat-sen University

Nature Communications, 2023, vol. 14, issue 1, 1-11

Abstract: Abstract Cyclobutanone is a strained motif with broad applications, while direct assembly of the aromatic ring fused cyclobutanones beyond benzocyclobutenone (BCB) skeletons remains challenging. Herein, we report a Rh-catalyzed formal [3+2] annulation of diazo group tethered alkynes involving a 4-exo-dig carbocyclization process, providing a straightforward access to furan-fused cyclobutanones. DFT calculations disclose that, by comparison to the competitive 5-endo-dig process, 4-exo-dig carbocyclization is mainly due to lower angle strain of the key sp-hybridized vinyl cationic transition state in the cyclization step. Using less reactive catalysts Rh2(carboxylate)4 is critical for high selectivity, which is explained as catalyst-substrate hydrogen bonding interaction. This method is proved successful to direct access previously inaccessible and unknown furan-fused cyclobutanone scaffolds, which can participate in a variety of post-functionalization reactions as versatile synthetic blocks. In addition, preliminary antitumor activity study of these products indicates that some molecules exhibite significant anticancer potency against different human cancer cell lines.

Date: 2023
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DOI: 10.1038/s41467-023-42032-9

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