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

doi:10.1021/acs.orglett.7b00681

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

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

54 Scopus citations

Abstract

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 language	English
Pages (from-to)	1906-1909
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	7
DOIs	https://doi.org/10.1021/acs.orglett.7b00681
State	Published - 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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10.1021/acs.orglett.7b00681

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title = "Visible-Light-Induced Synthesis of Carbazoles by in Situ Formation of Photosensitizing Intermediate",

abstract = "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.",

author = "Tanmay Chatterjee and Roh, {Geum Bee} and Shoaib, {Mahbubul Alam} and Suhl, {Chang Heon} and Kim, {Jun Soo} and Cho, {Cheon Gyu} and Cho, {Eun Jin}",

note = "Funding Information: This work was supported by the National Research Foundation of Korea (NRF-2014R1A1A1A05003274, 2014R1A5A1011165, and 2012M3A7B4049657). Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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doi = "10.1021/acs.orglett.7b00681",

language = "English",

volume = "19",

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T1 - Visible-Light-Induced Synthesis of Carbazoles by in Situ Formation of Photosensitizing Intermediate

AU - Chatterjee, Tanmay

AU - Roh, Geum Bee

AU - Shoaib, Mahbubul Alam

AU - Suhl, Chang Heon

AU - Kim, Jun Soo

AU - Cho, Cheon Gyu

AU - Cho, Eun Jin

N1 - Funding Information: This work was supported by the National Research Foundation of Korea (NRF-2014R1A1A1A05003274, 2014R1A5A1011165, and 2012M3A7B4049657). Publisher Copyright: © 2017 American Chemical Society.

PY - 2017/4/7

Y1 - 2017/4/7

N2 - 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.

AB - 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.

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JO - Organic Letters

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ER -

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

Abstract

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