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Relay Photocatalytic Reaction of N-Aryl Amino Acids and 2-Bromo-3,3,3-trifluoropropene: Synthesis of 4-(Difluoromethylidene)-tetrahydroquinolines.

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The bulk industrial chemical 2-bromo-3,3,3-trifluoropropene (BTP) was first employed as a coupling partner in photocatalytic defluorinative reactions with N-aryl amino acids. Photoredox activation of the C(sp2)-Br bond of the resultant… Click to show full abstract

The bulk industrial chemical 2-bromo-3,3,3-trifluoropropene (BTP) was first employed as a coupling partner in photocatalytic defluorinative reactions with N-aryl amino acids. Photoredox activation of the C(sp2)-Br bond of the resultant 2-bromo-1,1-difluoroalkenes generates gem-difluoro vinyl radicals for further radical cyclization. Various 4-(difluoromethylidene)-tetrahydroquinolines were assembled in good yields by combining two photoredox cycles with a single photocatalyst.

Keywords: amino acids; difluoromethylidene tetrahydroquinolines; bromo trifluoropropene; aryl amino; relay photocatalytic

Journal Title: Organic letters
Year Published: 2022

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