Radical Carbosulfonylation of Propellane: Synthesis of Sulfonyl β-Keto-bicyclo[1,1,1]pentanes

Yunlong Wei; Zhiqi Chen; Zhen Wu; Yaohui Xu; Xinxin Wu; Chen Zhu

doi:10.1055/a-1484-1028

Synthesis, Table of Contents

Synthesis 2021; 53(18): 3325-3332
DOI: 10.1055/a-1484-1028

special topic

Bond Activation – in Honor of Prof. Shinji Murai

Radical Carbosulfonylation of Propellane: Synthesis of Sulfonyl β-Keto-bicyclo[1,1,1]pentanes

Yunlong Wei‡

^aKey Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou 215123, Jiangsu, P. R. of China

,

Zhiqi Chen‡

^aKey Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou 215123, Jiangsu, P. R. of China

,

Zhen Wu

^aKey Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou 215123, Jiangsu, P. R. of China

,

Yaohui Xu

^aKey Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou 215123, Jiangsu, P. R. of China

,

Xinxin Wu

^aKey Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou 215123, Jiangsu, P. R. of China

,

Chen Zhu ∗

^aKey Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou 215123, Jiangsu, P. R. of China

^bKey Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China

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Abstract

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Abstract

The construction of multiply functionalized bicyclo[1.1.1]pentanes (BCPs) is of high synthetic value, as they are frequently harnessed as bioisosteres of 1,3-disubstituted benzene rings, alkynes, and tert-butyl groups in medicinal chemistry. Herein, we disclose a practical radical-mediated carbosulfonylation of propellane for the synthesis of sulfonyl β-keto-substituted BCPs by using vinyl sulfonates as dual-function reagent. This protocol features broad functional group tolerance and excellent atom-economy, leading to a variety of valuable difunctionalized BCP derivatives under mild photochemical conditions.

Key words

bicyclo[1.1.1]pentanes - propellane - sulfonylation - photochemical - C–C cleavage - radical reactions

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References

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