N-Bromosuccinimide (NBS)-Catalyzed C–H Bond Functionalization: An Annulation of Alkynes with Electron Withdrawing Group (EWG)-Substituted Acetyl Indoles for the Synthesis of Carbazoles
Han Wang
1
,
Zhen Wang
1
,
Yi-Long Wang
1
,
Rui Rui Zhou
1
,
Guang Chuan Wu
1
,
Si Yao Yin
1
,
Yan Xu
1
,
Bin Wang
1
Publication type: Journal Article
Publication date: 2017-11-02
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
29094599
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
An N-bromosuccinimide-catalyzed intermolecular annulation of acetyl indoles with alkynes was developed, allowing for regioselective formation of valuable carbazoles through direct C-H bond functionalization. The readily available catalyst, wide substrate scope, gram scale synthesis, and mild conditions make this method practical. Mechanistic investigations indicate that the bromination of acetyl indole takes place to generate a bromide intermediate, followed by coupling with an alkyne and intramolecular cycloaromatization to furnish carbazole products.
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Total citations:
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Citations from 2024:
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(13.04%)
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GOST
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Wang H. et al. N-Bromosuccinimide (NBS)-Catalyzed C–H Bond Functionalization: An Annulation of Alkynes with Electron Withdrawing Group (EWG)-Substituted Acetyl Indoles for the Synthesis of Carbazoles // Organic Letters. 2017. Vol. 19. No. 22. pp. 6140-6143.
GOST all authors (up to 50)
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Wang H., Wang Z., Wang Y., Zhou R. R., Wu G. C., Yin S. Y., Xu Y., Wang B. N-Bromosuccinimide (NBS)-Catalyzed C–H Bond Functionalization: An Annulation of Alkynes with Electron Withdrawing Group (EWG)-Substituted Acetyl Indoles for the Synthesis of Carbazoles // Organic Letters. 2017. Vol. 19. No. 22. pp. 6140-6143.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.orglett.7b03021
UR - https://doi.org/10.1021/acs.orglett.7b03021
TI - N-Bromosuccinimide (NBS)-Catalyzed C–H Bond Functionalization: An Annulation of Alkynes with Electron Withdrawing Group (EWG)-Substituted Acetyl Indoles for the Synthesis of Carbazoles
T2 - Organic Letters
AU - Wang, Han
AU - Wang, Zhen
AU - Wang, Yi-Long
AU - Zhou, Rui Rui
AU - Wu, Guang Chuan
AU - Yin, Si Yao
AU - Xu, Yan
AU - Wang, Bin
PY - 2017
DA - 2017/11/02
PB - American Chemical Society (ACS)
SP - 6140-6143
IS - 22
VL - 19
PMID - 29094599
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2017_Wang,
author = {Han Wang and Zhen Wang and Yi-Long Wang and Rui Rui Zhou and Guang Chuan Wu and Si Yao Yin and Yan Xu and Bin Wang},
title = {N-Bromosuccinimide (NBS)-Catalyzed C–H Bond Functionalization: An Annulation of Alkynes with Electron Withdrawing Group (EWG)-Substituted Acetyl Indoles for the Synthesis of Carbazoles},
journal = {Organic Letters},
year = {2017},
volume = {19},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/acs.orglett.7b03021},
number = {22},
pages = {6140--6143},
doi = {10.1021/acs.orglett.7b03021}
}
Cite this
MLA
Copy
Wang, Han, et al. “N-Bromosuccinimide (NBS)-Catalyzed C–H Bond Functionalization: An Annulation of Alkynes with Electron Withdrawing Group (EWG)-Substituted Acetyl Indoles for the Synthesis of Carbazoles.” Organic Letters, vol. 19, no. 22, Nov. 2017, pp. 6140-6143. https://doi.org/10.1021/acs.orglett.7b03021.