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volume 123 pages 32-37

Mechanistic and experimental study on copper-catalyzed C3-sulfenylation of indoles with sulfur powder and aryl iodides

Publication typeJournal Article
Publication date2019-04-01
scimago Q1
wos Q2
SJR0.811
CiteScore7.9
Impact factor4.3
ISSN15667367
General Chemistry
Catalysis
Process Chemistry and Technology
Abstract
The copper-catalyzed sulfenylation of indoles with aryl iodide and sulfur powder has been investigated both experimentally and theoretically. This protocol provides a direct and facile approach to prepare 3-sulfenylindoles with moderate to excellent yields and good functional-group tolerance. The in-situ IR analysis provided evidence for that NaOAc could promote the synthesis of diphenyl disulfide by the coupling of aryl iodide and sulfur powder. According to DFT calculations, the coupling pathway involving the intermediate N-methyl-3-iodoindole is more favored than the direct coupling by the C H activation of indole. The N-methyl-3-iodoindole was identified as a crucial intermediate in the catalytic cycle.
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GOST |
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GOST Copy
Ge X. et al. Mechanistic and experimental study on copper-catalyzed C3-sulfenylation of indoles with sulfur powder and aryl iodides // Catalysis Communications. 2019. Vol. 123. pp. 32-37.
GOST all authors (up to 50) Copy
Ge X., Cheng L., Sun F., Liu X., Chen X., Qian C., Zhou S. Mechanistic and experimental study on copper-catalyzed C3-sulfenylation of indoles with sulfur powder and aryl iodides // Catalysis Communications. 2019. Vol. 123. pp. 32-37.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1016/j.catcom.2019.01.015
UR - https://doi.org/10.1016/j.catcom.2019.01.015
TI - Mechanistic and experimental study on copper-catalyzed C3-sulfenylation of indoles with sulfur powder and aryl iodides
T2 - Catalysis Communications
AU - Ge, Xin
AU - Cheng, Lin
AU - Sun, Fengli
AU - Liu, Xuemin
AU - Chen, Xinzhi
AU - Qian, Chao
AU - Zhou, Shaodong
PY - 2019
DA - 2019/04/01
PB - Elsevier
SP - 32-37
VL - 123
SN - 1566-7367
ER -
BibTex
Cite this
BibTex (up to 50 authors) Copy
@article{2019_Ge,
author = {Xin Ge and Lin Cheng and Fengli Sun and Xuemin Liu and Xinzhi Chen and Chao Qian and Shaodong Zhou},
title = {Mechanistic and experimental study on copper-catalyzed C3-sulfenylation of indoles with sulfur powder and aryl iodides},
journal = {Catalysis Communications},
year = {2019},
volume = {123},
publisher = {Elsevier},
month = {apr},
url = {https://doi.org/10.1016/j.catcom.2019.01.015},
pages = {32--37},
doi = {10.1016/j.catcom.2019.01.015}
}