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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‡
a   Key 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‡
a   Key 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
a   Key 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
a   Key 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
a   Key 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  ∗
a   Key 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
b   Key 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
› Author AffiliationsC.Z. is grateful for the financial support from the National Natural Science Foundation of China (21971173), the Project of Scientific and Technologic Infrastructure of Suzhou (SZS201905), the Undergraduate Training Program for Innovation and Entrepreneurship, Soochow University (202010285003), and the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD).
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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1484-1028.
  • Supporting Information


Publication History

Received: 15 March 2021

Accepted after revision: 16 April 2021

Accepted Manuscript online:
16 April 2021

Article published online:
19 May 2021

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