Journal
CHEMICAL COMMUNICATIONS
Volume 57, Issue 49, Pages 6066-6069Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1cc02249k
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Funding
- National Natural Science Foundation of China [21971173]
- Project of Scientific and Technologic Infrastructure of Suzhou [SZS201905]
- Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD)
- Postgraduate Research & Practice Innovation Program of Jiangsu Province [KYCX20_2651]
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This study reveals an efficient and practical method for synthesizing sulfonyl alkynyl/allyl/cyano-substituted BCP derivatives through a novel radical-mediated difunctionalization of propellane, with broad functional group tolerance, high product diversity, gram-scale preparation, and excellent atom-economy.
Bicyclo[1.1.1]pentane (BCP) is widely applied as the bioisostere for aryl, internal alkynes, and tert-butyl groups in medicinal chemistry. We herein disclose an efficient and practical preparation of sulfonyl alkynyl/allyl/cyano-substituted BCP derivatives through a novel radical-mediated difunctionalization of propellane. The radical alkynylation, allylation, and cyanation processes readily proceed under mild photochemical conditions. The synthetic method features broad functional group tolerance, high product diversity, gram-scale preparation, and excellent atom-economy.
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