Hetero-Type Benzannulation Leading to Substituted Benzothio-Phenes

TiCl<sub>4</sub> (or SnCl<sub>4</sub>)-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 f...

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Autores principales:	Taro Kono, Ryosuke Sasaki, Hideki Goto, Masatoshi Kakuno, Yoo Tanabe
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	thiophene benzothiophene benzannulation gem-dichlorocyclopropane Suzuki–Miyaura cross-coupling hydroxylation Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/34479747e113498aab0d24246d7fb9fd
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id	oai:doaj.org-article:34479747e113498aab0d24246d7fb9fd
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spelling	oai:doaj.org-article:34479747e113498aab0d24246d7fb9fd2021-11-25T18:29:09ZHetero-Type Benzannulation Leading to Substituted Benzothio-Phenes10.3390/molecules262270081420-3049https://doaj.org/article/34479747e113498aab0d24246d7fb9fd2021-11-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/22/7008https://doaj.org/toc/1420-3049TiCl<sub>4</sub> (or SnCl<sub>4</sub>)-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)<sub>2</sub>/SPhos/K<sub>3</sub>PO<sub>4</sub> catalysis (seven examples; 63–91%), (ii) a hydroxylation using KOH/Pd(dba)<sub>2</sub>/tBu-XPhos catalysis (85%), and (iii) a borylation using a B<sub>2</sub>(pin)<sub>2</sub>/Pd(dba)<sub>2</sub>/XPhos/NaOAc catalysis-provided 4-(pin)B-benzothiophene (58%).Taro KonoRyosuke SasakiHideki GotoMasatoshi KakunoYoo TanabeMDPI AGarticlethiophenebenzothiophenebenzannulationgem-dichlorocyclopropaneSuzuki–Miyaura cross-couplinghydroxylationOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 7008, p 7008 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	thiophene benzothiophene benzannulation gem-dichlorocyclopropane Suzuki–Miyaura cross-coupling hydroxylation Organic chemistry QD241-441
spellingShingle	thiophene benzothiophene benzannulation gem-dichlorocyclopropane Suzuki–Miyaura cross-coupling hydroxylation Organic chemistry QD241-441 Taro Kono Ryosuke Sasaki Hideki Goto Masatoshi Kakuno Yoo Tanabe Hetero-Type Benzannulation Leading to Substituted Benzothio-Phenes
description	TiCl<sub>4</sub> (or SnCl<sub>4</sub>)-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)<sub>2</sub>/SPhos/K<sub>3</sub>PO<sub>4</sub> catalysis (seven examples; 63–91%), (ii) a hydroxylation using KOH/Pd(dba)<sub>2</sub>/tBu-XPhos catalysis (85%), and (iii) a borylation using a B<sub>2</sub>(pin)<sub>2</sub>/Pd(dba)<sub>2</sub>/XPhos/NaOAc catalysis-provided 4-(pin)B-benzothiophene (58%).
format	article
author	Taro Kono Ryosuke Sasaki Hideki Goto Masatoshi Kakuno Yoo Tanabe
author_facet	Taro Kono Ryosuke Sasaki Hideki Goto Masatoshi Kakuno Yoo Tanabe
author_sort	Taro Kono
title	Hetero-Type Benzannulation Leading to Substituted Benzothio-Phenes
title_short	Hetero-Type Benzannulation Leading to Substituted Benzothio-Phenes
title_full	Hetero-Type Benzannulation Leading to Substituted Benzothio-Phenes
title_fullStr	Hetero-Type Benzannulation Leading to Substituted Benzothio-Phenes
title_full_unstemmed	Hetero-Type Benzannulation Leading to Substituted Benzothio-Phenes
title_sort	hetero-type benzannulation leading to substituted benzothio-phenes
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/34479747e113498aab0d24246d7fb9fd
work_keys_str_mv	AT tarokono heterotypebenzannulationleadingtosubstitutedbenzothiophenes AT ryosukesasaki heterotypebenzannulationleadingtosubstitutedbenzothiophenes AT hidekigoto heterotypebenzannulationleadingtosubstitutedbenzothiophenes AT masatoshikakuno heterotypebenzannulationleadingtosubstitutedbenzothiophenes AT yootanabe heterotypebenzannulationleadingtosubstitutedbenzothiophenes
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Hetero-Type Benzannulation Leading to Substituted Benzothio-Phenes

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