Benzannulation of heterocyclic frameworks by 1,1-carboboration pathways.
Publication type: Journal Article
Publication date: 2015-02-02
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
25581248
Organic Chemistry
Abstract
A small series of S- and N-heterocyclic 1,2-bis(trimethylsilylethynyl)arenes (2, 9, and 12) react with the strongly electrophilic borane B(C6F5)3 in consecutive 1,1-carboboration sequences to benzannulated heterocyclic systems. With this approach, highly substituted carbazole (6), benzothiophene (10), and quinoline (14) derivatives can be synthesized. While benzannulation occurs in all three cases, the reactions are quite different in detail. Finally, one-pot deborylation reactions lead to hydroxy-hetarenes, as demonstrated for the hydroxy-carbazole 7 and the hydroxy-benzothiophene 11.
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35
Total citations:
35
Citations from 2024:
2
(5.71%)
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GOST
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Liedtke R. et al. Benzannulation of heterocyclic frameworks by 1,1-carboboration pathways. // Journal of Organic Chemistry. 2015. Vol. 80. No. 4. pp. 2240-2248.
GOST all authors (up to 50)
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Liedtke R., Tenberge F., Daniliuc C. G., Kehr G., Erker G. Benzannulation of heterocyclic frameworks by 1,1-carboboration pathways. // Journal of Organic Chemistry. 2015. Vol. 80. No. 4. pp. 2240-2248.
Cite this
RIS
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TY - JOUR
DO - 10.1021/jo502753s
UR - https://doi.org/10.1021/jo502753s
TI - Benzannulation of heterocyclic frameworks by 1,1-carboboration pathways.
T2 - Journal of Organic Chemistry
AU - Liedtke, René
AU - Tenberge, Fabian
AU - Daniliuc, Constantin G.
AU - Kehr, Gerald
AU - Erker, Gerhard
PY - 2015
DA - 2015/02/02
PB - American Chemical Society (ACS)
SP - 2240-2248
IS - 4
VL - 80
PMID - 25581248
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{2015_Liedtke,
author = {René Liedtke and Fabian Tenberge and Constantin G. Daniliuc and Gerald Kehr and Gerhard Erker},
title = {Benzannulation of heterocyclic frameworks by 1,1-carboboration pathways.},
journal = {Journal of Organic Chemistry},
year = {2015},
volume = {80},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021/jo502753s},
number = {4},
pages = {2240--2248},
doi = {10.1021/jo502753s}
}
Cite this
MLA
Copy
Liedtke, René, et al. “Benzannulation of heterocyclic frameworks by 1,1-carboboration pathways..” Journal of Organic Chemistry, vol. 80, no. 4, Feb. 2015, pp. 2240-2248. https://doi.org/10.1021/jo502753s.