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

59 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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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.",

year = "2017",

month = apr,

day = "7",

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

language = "English",

volume = "19",

pages = "1906--1909",

journal = "Organic Letters",

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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.

UR - https://www.scopus.com/pages/publications/85017183008

U2 - 10.1021/acs.orglett.7b00681

DO - 10.1021/acs.orglett.7b00681

M3 - Article

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AN - SCOPUS:85017183008

SN - 1523-7060

VL - 19

SP - 1906

EP - 1909

JO - Organic Letters

JF - Organic Letters

IS - 7

ER -

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

Abstract

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