Journal
SYNTHESIS-STUTTGART
Volume 53, Issue 18, Pages 3325-3332Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/a-1484-1028
Keywords
bicyclo[1.1.1]pentanes; propellane; sulfonylation; photochemical; C-C cleavage; radical reactions
Categories
Funding
- National Natural Science Foundation of China [21971173]
- Project of Scientific and Technologic Infrastructure of Suzhou [SZS201905]
- Undergraduate Training Program for Innovation and Entrepreneurship, Soochow University [202010285003]
- Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD)
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The study presents a method for synthesizing sulfonyl beta-keto-substituted BCPs through a carbosulfonylation reaction, using vinyl sulfonates as dual-function reagent, with broad functional group tolerance and excellent atom-economy under mild photochemical conditions.
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 beta-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.
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