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

Tanmay Chatterjee, Geum Bee Roh, Mahbubul Alam Shoaib, Chang Heon Suhl, Jun Soo Kim, Cheon Gyu Cho, Eun Jin Cho

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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.

Original languageEnglish
Pages (from-to)1906-1909
Number of pages4
JournalOrganic Letters
Issue number7
StatePublished - 7 Apr 2017

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation of Korea (NRF-2014R1A1A1A05003274, 2014R1A5A1011165, and 2012M3A7B4049657).

Publisher Copyright:
© 2017 American Chemical Society.


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