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Molecules
,  volume 26 ,  issue 22 ,  pages 7008

Hetero-Type Benzannulation Leading to Substituted Benzothio-Phenes

Publication type: Journal Article
Publication date: 2021-11-19
MDPI
scimago Q1
wos Q2
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)
Abstract

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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GOST |
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GOST Copy
Kono T. et al. Hetero-Type Benzannulation Leading to Substituted Benzothio-Phenes // Molecules. 2021. Vol. 26. No. 22. p. 7008.
GOST all authors (up to 50) Copy
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.
RIS |
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RIS Copy
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 -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@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}
}
MLA
Cite this
MLA Copy
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.