Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 29, Issue 36, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202300978
Keywords
benzylic C-H oxidation; indoles; photocatalysis; remote halogenation
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A mild and catalyst-free sunlight induced protocol for the remote meta bromination of electron-deficient indoles is described for the first time. Herein, N-bromosaccharin is activated by sunlight irradiation. Alternately, a synergistic activation model (Sc(OTf)(3)/HFIP) has also been developed for the activation of haloniums, complementary to the light induced strategy. In addition, the cascade C6-H bromination and benzylic C-H oxidation under photocatalytic conditions was also discussed. High regio-and chem-selectivity, mild reaction conditions, and scalability demonstrate great potential of the developed methods in practical applications and further functionalization.
A mild and catalyst-free sunlight induced protocol for the remote meta bromination of electron-deficient indoles is described for the first time. Herein, N-bromosaccharin is activated by sunlight irradiation. Alternately, a synergistic activation model (Sc(OTf)(3)/HFIP) has also been developed for the activation of haloniums, complementary to the light induced strategy. In addition, the cascade C6-H bromination and benzylic C-H oxidation under photocatalytic conditions was also discussed. High regio-and chem-selectivity, mild reaction conditions, and scalability demonstrate great potential of the developed methods in practical applications and further functionalization.
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