American Chemical Society
ol7b00681_si_001.pdf (2.41 MB)

Visible-Light-Induced Synthesis of Carbazoles by in Situ Formation of Photosensitizing Intermediate

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journal contribution
posted on 2017-03-28, 20:25 authored by Tanmay Chatterjee, Geum-bee Roh, Mahbubul Alam Shoaib, Chang-Heon Suhl, Jun Soo Kim, Cheon-Gyu Cho, Eun Jin Cho
A visible-light-induced synthesis of N-H carbazoles from easily accessible 2,2′-diaminobiaryls in the absence of any external photosensitizer is reported. The process only requires tBuONO and natural resources, visible light, and molecular oxygen for the synthesis of N-H carbazoles. Experimental and computational studies support that the in situ formation of a visible-light-absorbing photosensitizing intermediate, benzocinnoline N-imide, is responsible for the activation of triplet molecular oxygen to singlet oxygen that, in turn, promotes the synthesis of carbazole.