A diastereoselective synthesis of cyclopentanones via photocatalytic reductive alkyltrifluoromethylation of ynones. Issue 20 (30th August 2022)

• Record Type: Journal Article
• Authors: Qiu, Jiayan; Le, Siya; Su, Jingwen; Liu, Yi; Zhou, Yulu; Zheng, Hanliang; Bai, Yihui; Zhu, Gangguo
• Is Part Of: Organic chemistry frontiers. Volume 9:Issue 20(2022)
• Page Start: 5523
• Page End: 5529
• Publication Date: 2022-08-30
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d2qo01101h
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A photocatalytic reductive alkyltrifluoromethylation of ynones with the Langlois reagent is developed, providing a regio- and diastereoselective access to trifluoromethylated cyclopentanones under mild conditions. Abstract : Traditional alkyne carbotrifluoromethylation protocols lead to the production of trifluoromethylated alkenes, while new reaction modes remain to be explored. Herein, a visible light induced reductive alkyltrifluoromethylation of ynones with the Langlois reagent is developed, providing a regio- and diastereoselective access to highly functionalized trifluoromethylated cyclopentanones at room temperature. Mechanistic studies suggest a radical pathway involving the regioselective trifluoromethylation of C–C triple bonds, 1, 5-HAT, 5- endo-trig closure, single electron transfer reduction, and protonation.