Rhodium-catalyzed C-H α-fluoroalkenylation/annulation of β-ketosulfoxonium ylides with 2,2-difluorovinyl tosylate/oxadiazolones

Jia-Lin Song; Zi-Feng Yang; Sheng Fang; Wang-Liang Chen; Lian-Bao Ye; Xiang Liu; Bing Shu

doi:10.1039/d4cc05621c

Rhodium-catalyzed C-H α-fluoroalkenylation/annulation of β-ketosulfoxonium ylides with 2,2-difluorovinyl tosylate/oxadiazolones

Chem Commun (Camb). 2024 Dec 12;60(100):15000-15003. doi: 10.1039/d4cc05621c.

Authors

Jia-Lin Song^{1

2}, Zi-Feng Yang³, Sheng Fang¹, Wang-Liang Chen¹, Lian-Bao Ye¹, Xiang Liu³, Bing Shu^{1

4}

Affiliations

¹ School of Pharmacy, Guangdong Pharmaceutical University, Guangzhou, 510006, P. R. China. yelianbao@gdpu.edu.cnl.
² School of Chemistry, Sun Yat-sen University, Guangzhou, 510006, P. R. China.
³ School of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, Zhongshan, 528458, P. R. China. liux96@gdpu.edu.cn.
⁴ Guangdong Provincial Key Laboratory for Research and Evaluation of Pharmaceutical Preparations, Guangdong Pharmaceutical University, Guangzhou, 510006, P. R. China.

PMID: 39600176
DOI: 10.1039/d4cc05621c

Abstract

A Rh(III)-catalyzed C-H α-fluoroalkenylation/annulation of β-ketosulfoxonium ylides with 2,2-difluorovinyl tosylate/oxadiazolones was realized, which afforded various o-fluoroalkenylation β-ketosulfoxonium ylides with high Z-selectivity and diverse oxadiazolone fused-isoquinolines. This protocol featured mild conditions, broad substrate scope, and functional-group compatibility. In addition, scale-up synthesis, related applications and preliminary mechanistic explorations were also accomplished.