Cp*Ir(iii) and Cp*Rh(iii)-catalyzed annulation of salicylaldehydes with fluorinated vinyl tosylates. Issue 64 (21st July 2022)

• Record Type: Journal Article
• Authors: Zhao, Shuwen; Cai, Xiaojia; Lu, Yuying; Hu, Jinhui; Xiong, Zhuang; Jin, Jingwei; Li, Yin; Wang, Honggen; Wu, Jia-Qiang
• Is Part Of: Chemical communications. Volume 58:Issue 64(2022)
• Page Start: 8966
• Page End: 8969
• Publication Date: 2022-07-21
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d2cc02194c
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : A versatile hydroxy-directed aldehyde C–H activation/annulation of salicylaldehydes with fluorovinyl tosylates enables the synthesis of diverse 2, 3-non-substituted and 2-fluoroalkoxy-substituted chromones via Cp*Ir(iii ) or Cp*Rh(iii ) catalysis. Abstract : A mild, selective and redox-neutral Cp*Ir(iii )- and Cp*Rh(iii )-catalyzed C–H activation/annulation of salicylaldehydes with fluorovinyl tosylates is reported. The use of monofluorovinyl tosylate favors the synthesis of C2- and C3-substitution-free chromones via C–H activation/β-F elimination/annulation, whereas difluorovinyl tosylate leads to the construction of C2-fluoroalkoxy chromones. Mild reaction conditions and good functional-group tolerance were observed. Further functionalization of the resulting chromones via halogenation, alkynylation, alkylation and hydrocyanation was successfully realized.