CsPbBr 3 Perovskite Photocatalyst in Chemodivergent Functionalization of N -Methylalkanamides Using CBr 4 .
Buddhadeb PalAshis MathuriAnupam MannaPrasenjit MalPublished in: Organic letters (2023)
Herein we have developed a strategy for chemodivergent functionalization of N- methylalkanamides via C-Br bond activation of CBr 4 , using an orthorhombic CsPbBr 3 perovskite photocatalyst under blue LEDs (450-470 nm). The selectivity of whether a 5-exo-trig spiro cyclization or a 6-endo-trig cyclization occurred depended on the stability of the radical intermediate that was formed after the addition of the bromide radical to the starting compound to obtain 3,8-dibromo-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-trien-2-on or 3-bromo-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione or 3-bromo-6-( tert -butyl)-1-methyl-4-phenylquinolin-2(1 H )-one.