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Published on: May 21, 2019
CsPbBr3 Perovskite Photocatalyst in Chemodivergent Functionalization of N-Methylalkanamides Using CBr4
Buddhadeb Pal1, Ashis Mathuri1, Anupam Manna1
1School of Chemical Sciences, National Institute of Science Education and Research (NISER), An OCC of Homi Bhabha National Institute, Jatni, Bhubaneswar, District Khurda, Odisha 752050, India.
Abstract:
Herein we have developed a strategy for chemodivergent functionalization of N-methylalkanamides via C-Br bond activation of CBr4, using an orthorhombic CsPbBr3 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(1H)-one.
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