Metal-Free Dehydrogenative Diels-Alder Reactions of 2-Methyl-3-Alkylindoles with Dienophiles: Rapid Access to Tetrahydrocarbazoles, Carbazoles, and Heteroacenes
Publication type: Journal Article
Publication date: 2015-06-10
scimago Q1
wos Q1
SJR: 5.550
CiteScore: 27.6
Impact factor: 16.9
ISSN: 14337851, 15213773
PubMed ID:
26096824
General Chemistry
Catalysis
Abstract
An unprecedented strategy for in situ generation of indole-based ortho-quinodimethanes (oQDMs) from 2-methyl-3-alkylmethylindoles by either a metal-free DDQ- or BQ-mediated dehydrogenative process was developed. These oQDMs were trapped by electron-deficient dienophiles to provide a facile approach to synthetically valuable tetrahydrocarbazoles, carbazoles, and hetereoacenes. The salient features of this transformation include direct C(sp(3))-H bond functionalizations, readily available starting materials, metal-free conditions, high efficiency, operational simplicity, and ease of scale-up.
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85
Total citations:
85
Citations from 2024:
11
(12.94%)
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Zhou L., Xu B., Zhang J. Metal-Free Dehydrogenative Diels-Alder Reactions of 2-Methyl-3-Alkylindoles with Dienophiles: Rapid Access to Tetrahydrocarbazoles, Carbazoles, and Heteroacenes // Angewandte Chemie - International Edition. 2015. Vol. 54. No. 31. pp. 9092-9096.
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Zhou L., Xu B., Zhang J. Metal-Free Dehydrogenative Diels-Alder Reactions of 2-Methyl-3-Alkylindoles with Dienophiles: Rapid Access to Tetrahydrocarbazoles, Carbazoles, and Heteroacenes // Angewandte Chemie - International Edition. 2015. Vol. 54. No. 31. pp. 9092-9096.
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TY - JOUR
DO - 10.1002/anie.201503549
UR - https://doi.org/10.1002/anie.201503549
TI - Metal-Free Dehydrogenative Diels-Alder Reactions of 2-Methyl-3-Alkylindoles with Dienophiles: Rapid Access to Tetrahydrocarbazoles, Carbazoles, and Heteroacenes
T2 - Angewandte Chemie - International Edition
AU - Zhou, Liejin
AU - Xu, Bing
AU - Zhang, Junliang
PY - 2015
DA - 2015/06/10
PB - Wiley
SP - 9092-9096
IS - 31
VL - 54
PMID - 26096824
SN - 1433-7851
SN - 1521-3773
ER -
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BibTex (up to 50 authors)
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@article{2015_Zhou,
author = {Liejin Zhou and Bing Xu and Junliang Zhang},
title = {Metal-Free Dehydrogenative Diels-Alder Reactions of 2-Methyl-3-Alkylindoles with Dienophiles: Rapid Access to Tetrahydrocarbazoles, Carbazoles, and Heteroacenes},
journal = {Angewandte Chemie - International Edition},
year = {2015},
volume = {54},
publisher = {Wiley},
month = {jun},
url = {https://doi.org/10.1002/anie.201503549},
number = {31},
pages = {9092--9096},
doi = {10.1002/anie.201503549}
}
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MLA
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Zhou, Liejin, et al. “Metal-Free Dehydrogenative Diels-Alder Reactions of 2-Methyl-3-Alkylindoles with Dienophiles: Rapid Access to Tetrahydrocarbazoles, Carbazoles, and Heteroacenes.” Angewandte Chemie - International Edition, vol. 54, no. 31, Jun. 2015, pp. 9092-9096. https://doi.org/10.1002/anie.201503549.