Metal-Free C–H Functionalization and Aromatization Sequence for the Synthesis of 1-(Indol-3-yl)carbazoles and Total Synthesis of 7-Bromo-1-(6-bromo-1H-indol-3-yl)-9H-carbazole
Тип публикации: Journal Article
Дата публикации: 2019-01-24
scimago Q1
wos Q1
БС1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5
ISSN: 15237060, 15237052
PubMed ID:
30675785
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Краткое описание
An operationally simple, metal-free, cost-effective, and mild oxidative cross-coupling protocol for the synthesis of 1-indolyl tetrahydrocarbazoles to afford 1-(indol-3-yl)carbazoles is developed. N-Chlorosuccinimide is used as a mild oxidant for the functionalization of the 1-position of tetrahydrocarbazoles, aromatization of which furnished 1-(indol-3-yl)carbazoles in good to moderate yields without employing protection/deprotection strategy. A naturally rare dibromo 1-(indol-3-yl)carbazole alkaloid was synthesized for the first time in two steps with an overall yield of 64% by applying the same methodology.
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Ranjani G., Nagarajan R. Metal-Free C–H Functionalization and Aromatization Sequence for the Synthesis of 1-(Indol-3-yl)carbazoles and Total Synthesis of 7-Bromo-1-(6-bromo-1H-indol-3-yl)-9H-carbazole // Organic Letters. 2019. Vol. 21. No. 3. pp. 675-678.
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Ranjani G., Nagarajan R. Metal-Free C–H Functionalization and Aromatization Sequence for the Synthesis of 1-(Indol-3-yl)carbazoles and Total Synthesis of 7-Bromo-1-(6-bromo-1H-indol-3-yl)-9H-carbazole // Organic Letters. 2019. Vol. 21. No. 3. pp. 675-678.
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TY - JOUR
DO - 10.1021/acs.orglett.8b03848
UR - https://doi.org/10.1021/acs.orglett.8b03848
TI - Metal-Free C–H Functionalization and Aromatization Sequence for the Synthesis of 1-(Indol-3-yl)carbazoles and Total Synthesis of 7-Bromo-1-(6-bromo-1H-indol-3-yl)-9H-carbazole
T2 - Organic Letters
AU - Ranjani, Ganapathy
AU - Nagarajan, Rajagopal
PY - 2019
DA - 2019/01/24
PB - American Chemical Society (ACS)
SP - 675-678
IS - 3
VL - 21
PMID - 30675785
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2019_Ranjani,
author = {Ganapathy Ranjani and Rajagopal Nagarajan},
title = {Metal-Free C–H Functionalization and Aromatization Sequence for the Synthesis of 1-(Indol-3-yl)carbazoles and Total Synthesis of 7-Bromo-1-(6-bromo-1H-indol-3-yl)-9H-carbazole},
journal = {Organic Letters},
year = {2019},
volume = {21},
publisher = {American Chemical Society (ACS)},
month = {jan},
url = {https://doi.org/10.1021/acs.orglett.8b03848},
number = {3},
pages = {675--678},
doi = {10.1021/acs.orglett.8b03848}
}
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MLA
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Ranjani, Ganapathy, and Rajagopal Nagarajan. “Metal-Free C–H Functionalization and Aromatization Sequence for the Synthesis of 1-(Indol-3-yl)carbazoles and Total Synthesis of 7-Bromo-1-(6-bromo-1H-indol-3-yl)-9H-carbazole.” Organic Letters, vol. 21, no. 3, Jan. 2019, pp. 675-678. https://doi.org/10.1021/acs.orglett.8b03848.