Convenient and efficient access to tri- and tetra-substituted 4-fluoropyridines via a [3+2]/[2+1] cyclization reaction

作者：Tang, Xuejiao; Liu, Kun; Qu, Zeming; Zhan, Junyan; Zhu, Rukui; Teng, Fan; Meng, Lili; Huang, Yanmin; Huang, Chusheng; He, Yimiao^*; Zhu, Qiang

来源：CHINESE CHEMICAL LETTERS, 2022, 33(6): 2982-2986.

DOI：10.1016/j.cclet.2022.02.031

• 4-Fluoropyridine
• gem-Difluorocyclopropene
• [3+2]/[2+1] cyclization reaction
• DMSO as an oxidant
• Regioselectivity
• PKM2 modulator

A [3 + 2]/[2 + 1] cycloaddition reaction of gem-difluorocyclopropenes is presented, offering a mild and efficient approach to accessing tri- and tetra-substituted 4-fluoropyridines in moderate to good yields with excellent regioselectivity. Multiple synthetic applications, including process-scale reactions, modification of bioactive molecules, derivatization reactions and synthesis of the analogue of the PKM2 modulator, are subsequently described.

• 单位
  中国科学院; 南昌航空大学