Photoredox Catalysis Induced Bisindolylation of Ethers/Alcohols via Sequential C-H and C-O Bond Cleavage

Lu Ye; Sai Hu Cai; Ding Xing Wang; Yi Qiu Wang; Lin Jie Lai; Chao Feng; Teck Peng Loh

doi:10.1021/acs.orglett.7b03073

Photoredox Catalysis Induced Bisindolylation of Ethers/Alcohols via Sequential C-H and C-O Bond Cleavage

Lu Ye, Sai Hu Cai, Ding Xing Wang, Yi Qiu Wang, Lin Jie Lai, Chao Feng^*, Teck Peng Loh

^*Corresponding author for this work

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

46 Citations (Scopus)

Abstract

A visible-light-engaged 2-fold site-selective alkylation of indole derivatives with aliphatic ethers or alcohols has been accomplished for easy access to symmetric 3,3′-bisindolylmethane derivatives. The experimental data suggest a sequential photoredox catalysis induced radical addition and proton-mediated Friedel-Crafts alkylation mechanism.

Original language	English
Pages (from-to)	6164-6167
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	22
DOIs	https://doi.org/10.1021/acs.orglett.7b03073
Publication status	Published - Nov 17 2017
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2017 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.7b03073

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title = "Photoredox Catalysis Induced Bisindolylation of Ethers/Alcohols via Sequential C-H and C-O Bond Cleavage",

abstract = "A visible-light-engaged 2-fold site-selective alkylation of indole derivatives with aliphatic ethers or alcohols has been accomplished for easy access to symmetric 3,3′-bisindolylmethane derivatives. The experimental data suggest a sequential photoredox catalysis induced radical addition and proton-mediated Friedel-Crafts alkylation mechanism.",

author = "Lu Ye and Cai, {Sai Hu} and Wang, {Ding Xing} and Wang, {Yi Qiu} and Lai, {Lin Jie} and Chao Feng and Loh, {Teck Peng}",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

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doi = "10.1021/acs.orglett.7b03073",

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AU - Ye, Lu

AU - Cai, Sai Hu

AU - Wang, Ding Xing

AU - Wang, Yi Qiu

AU - Lai, Lin Jie

AU - Feng, Chao

AU - Loh, Teck Peng

PY - 2017/11/17

Y1 - 2017/11/17

N2 - A visible-light-engaged 2-fold site-selective alkylation of indole derivatives with aliphatic ethers or alcohols has been accomplished for easy access to symmetric 3,3′-bisindolylmethane derivatives. The experimental data suggest a sequential photoredox catalysis induced radical addition and proton-mediated Friedel-Crafts alkylation mechanism.

AB - A visible-light-engaged 2-fold site-selective alkylation of indole derivatives with aliphatic ethers or alcohols has been accomplished for easy access to symmetric 3,3′-bisindolylmethane derivatives. The experimental data suggest a sequential photoredox catalysis induced radical addition and proton-mediated Friedel-Crafts alkylation mechanism.

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Photoredox Catalysis Induced Bisindolylation of Ethers/Alcohols via Sequential C-H and C-O Bond Cleavage

Abstract

Bibliographical note

ASJC Scopus Subject Areas

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