A photoinduced reaction of perfluoroalkyl halides with 1, 3-diarylprop-2-yn-1-ones catalyzed by DABSO. Issue 9 (7th June 2017)

• Record Type: Journal Article
• Authors: Li, Yuewen; Lu, Yiye; Mao, Runyu; Li, Zhiming; Wu, Jie
• Is Part Of: Organic chemistry frontiers. Volume 4:Issue 9(2017)
• Page Start: 1745
• Page End: 1750
• Publication Date: 2017-06-07
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c7qo00279c
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : The sulfur dioxide surrogate of DABCO·(SO2 )2 is used as an efficient catalyst for the cleavage of the perfluoroalkyl-halogen bond under visible-light irradiation. A plausible mechanism supported by theoretical calculations is proposed. Abstract : The sulfur dioxide surrogate of DABCO·(SO2 )2 is used as an efficient catalyst for the cleavage of the perfluoroalkyl-halogen bond under visible-light irradiation for the first time. This unexpected reaction of perfluoroalkyl halides and 1, 3-diarylprop-2-yn-1-ones catalyzed by DABCO·(SO2 )2 in the presence of visible light proceeds smoothly, leading to 3-fluorinated indenones in good yields. During the reaction process, the cleavage of the perfluoroalkyl-halogen bond and subsequent radical oxidative cyclization are involved under metal-free conditions. A broad reaction scope is observed. Moreover, a plausible mechanism supported by theoretical calculations is proposed.