Radical Multicomponent Alkyl Alkynylation of Propellane via Synergistic Photoredox and Copper Catalysis

Bicyclo­[1.1.1]­pentanes (BCPs) are important bioisosteres of aryl, tert-butyl groups, and internal alkynes that can impact key physicochemical properties on drug candidates. Herein, we describe a novel and efficient reaction to synthesize alkyl-alkynyl-substituted BCP derivatives by synergistic pho...

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Published inOrganic letters Vol. 24; no. 25; pp. 4609 - 4614
Main Authors Shi, Jie, Xu, Qiao-Lin, Ni, Yu-Qing, Li, Lin, Pan, Fei
Format Journal Article
LanguageEnglish
Published American Chemical Society 01.07.2022
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Summary:Bicyclo­[1.1.1]­pentanes (BCPs) are important bioisosteres of aryl, tert-butyl groups, and internal alkynes that can impact key physicochemical properties on drug candidates. Herein, we describe a novel and efficient reaction to synthesize alkyl-alkynyl-substituted BCP derivatives by synergistic photoredox and copper catalysis at room temperature. The mild reaction conditions, simple protocol, broad functional group tolerance, and high efficiency of this procedure make it a valuable strategy for accessing alkynyl-substituted BCPs.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01721