Facile synthesis of benzo[: B] thiophenes via metal-free radical-triggered intramolecular C-S bond formation

Wei Fan; Kwong Yuen Chen; Qi Peng Chen; Guigen Li; Bo Jiang

doi:10.1039/c7ob01515a

Facile synthesis of benzo[: B] thiophenes via metal-free radical-triggered intramolecular C-S bond formation

Wei Fan, Kwong Yuen Chen, Qi Peng Chen, Guigen Li, Bo Jiang

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

Abstract

A facile method for the synthesis of benzo[b]thiophenes with good to excellent yields via metal-free intramolecular C-S bond formation has been developed by utilizing I₂ as a catalyst and O₂ from air as an oxidant (20 examples). Its notable features such as catalytic I₂, intramolecular C-S bond formation, short reaction times, and broad functional group tolerance make this strategy highly attractive. The purification of products only needs washing with solvents, thereby avoiding traditional chromatography and recrystallization, which belongs to group-assisted purification (GAP) chemistry.

Original language	English
Pages (from-to)	6493-6499
Number of pages	7
Journal	Organic and Biomolecular Chemistry
Volume	15
Issue number	31
DOIs	https://doi.org/10.1039/c7ob01515a
State	Published - 2017

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title = "Facile synthesis of benzo[: B] thiophenes via metal-free radical-triggered intramolecular C-S bond formation",

abstract = "A facile method for the synthesis of benzo[b]thiophenes with good to excellent yields via metal-free intramolecular C-S bond formation has been developed by utilizing I2 as a catalyst and O2 from air as an oxidant (20 examples). Its notable features such as catalytic I2, intramolecular C-S bond formation, short reaction times, and broad functional group tolerance make this strategy highly attractive. The purification of products only needs washing with solvents, thereby avoiding traditional chromatography and recrystallization, which belongs to group-assisted purification (GAP) chemistry.",

author = "Wei Fan and Chen, {Kwong Yuen} and Chen, {Qi Peng} and Guigen Li and Bo Jiang",

note = "Funding Information: We are grateful to the NSFC (No. 21332005 and 21672100), the Robert A. Welch Foundation (D-1361, USA), the PAPD of Jiangsu Higher Education Institutions, and the NSF of Jiangsu Province (BK20151163) for financial support. Publisher Copyright: {\textcopyright} 2017 The Royal Society of Chemistry.",

year = "2017",

doi = "10.1039/c7ob01515a",

language = "English",

volume = "15",

pages = "6493--6499",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

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T2 - B] thiophenes via metal-free radical-triggered intramolecular C-S bond formation

AU - Fan, Wei

AU - Chen, Kwong Yuen

AU - Chen, Qi Peng

AU - Li, Guigen

AU - Jiang, Bo

N1 - Funding Information: We are grateful to the NSFC (No. 21332005 and 21672100), the Robert A. Welch Foundation (D-1361, USA), the PAPD of Jiangsu Higher Education Institutions, and the NSF of Jiangsu Province (BK20151163) for financial support. Publisher Copyright: © 2017 The Royal Society of Chemistry.

PY - 2017

Y1 - 2017

N2 - A facile method for the synthesis of benzo[b]thiophenes with good to excellent yields via metal-free intramolecular C-S bond formation has been developed by utilizing I2 as a catalyst and O2 from air as an oxidant (20 examples). Its notable features such as catalytic I2, intramolecular C-S bond formation, short reaction times, and broad functional group tolerance make this strategy highly attractive. The purification of products only needs washing with solvents, thereby avoiding traditional chromatography and recrystallization, which belongs to group-assisted purification (GAP) chemistry.

AB - A facile method for the synthesis of benzo[b]thiophenes with good to excellent yields via metal-free intramolecular C-S bond formation has been developed by utilizing I2 as a catalyst and O2 from air as an oxidant (20 examples). Its notable features such as catalytic I2, intramolecular C-S bond formation, short reaction times, and broad functional group tolerance make this strategy highly attractive. The purification of products only needs washing with solvents, thereby avoiding traditional chromatography and recrystallization, which belongs to group-assisted purification (GAP) chemistry.

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JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 31

ER -

Facile synthesis of benzo[: B] thiophenes via metal-free radical-triggered intramolecular C-S bond formation

Abstract

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