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Molecules
,  том 26 ,  издание 22 ,  страницы 7008

Hetero-Type Benzannulation Leading to Substituted Benzothio-Phenes

Тип публикации: Journal Article
Дата публикации: 2021-11-19
MDPI
scimago Q1
wos Q2
БС1
SJR: 0.865
CiteScore: 8.6
Impact factor: 4.6
ISSN: 14203049
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
Краткое описание

TiCl4 (or SnCl4)-promoted hetero-type benzannulation reactions using various (2,2-dichlorocyclopropyl)(thiophen-2-yl)methanols proceeded smoothly to produce uniquely substituted 4-chlorobenzothiophenes (five examples). The present approach involves the first distinctive thiophene formation from thiophene cores, in contrast to traditional methods of thiophene formation from benzene cores. The stereocongested (less reactive) Cl position in the obtained 4-chlorobenzothiophenes functioned successfully as the partners of three cross-coupling reactions: (i) a Suzuki–Miyaura cross-couplings using Pd(OAc)2/SPhos/K3PO4 catalysis (seven examples; 63–91%), (ii) a hydroxylation using KOH/Pd(dba)2/tBu-XPhos catalysis (85%), and (iii) a borylation using a B2(pin)2/Pd(dba)2/XPhos/NaOAc catalysis-provided 4-(pin)B-benzothiophene (58%).

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Russian Chemical Reviews
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 100%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
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Kono T. et al. Hetero-Type Benzannulation Leading to Substituted Benzothio-Phenes // Molecules. 2021. Vol. 26. No. 22. p. 7008.
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Kono T., Sasaki R., Goto H., Kakuno M., Tanabe Y. Hetero-Type Benzannulation Leading to Substituted Benzothio-Phenes // Molecules. 2021. Vol. 26. No. 22. p. 7008.
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TY - JOUR
DO - 10.3390/molecules26227008
UR - https://doi.org/10.3390/molecules26227008
TI - Hetero-Type Benzannulation Leading to Substituted Benzothio-Phenes
T2 - Molecules
AU - Kono, Taro
AU - Sasaki, Ryosuke
AU - Goto, Hideki
AU - Kakuno, Masatoshi
AU - Tanabe, Yoo
PY - 2021
DA - 2021/11/19
PB - MDPI
SP - 7008
IS - 22
VL - 26
PMID - 34834100
SN - 1420-3049
ER -
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@article{2021_Kono,
author = {Taro Kono and Ryosuke Sasaki and Hideki Goto and Masatoshi Kakuno and Yoo Tanabe},
title = {Hetero-Type Benzannulation Leading to Substituted Benzothio-Phenes},
journal = {Molecules},
year = {2021},
volume = {26},
publisher = {MDPI},
month = {nov},
url = {https://doi.org/10.3390/molecules26227008},
number = {22},
pages = {7008},
doi = {10.3390/molecules26227008}
}
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Kono, Taro, et al. “Hetero-Type Benzannulation Leading to Substituted Benzothio-Phenes.” Molecules, vol. 26, no. 22, Nov. 2021, p. 7008. https://doi.org/10.3390/molecules26227008.