I2/O2-Enabled N-S Bond Formation to Access Functionalized 1,2,3-Thiadiazoles

Wei Fan; Qun Li; Yanrong Li; Hao Sun; Bo Jiang; Guigen Li

doi:10.1021/acs.orglett.6b00079

I₂/O₂-Enabled N-S Bond Formation to Access Functionalized 1,2,3-Thiadiazoles

Wei Fan, Qun Li, Yanrong Li, Hao Sun, Bo Jiang, Guigen Li

Chemistry and Biochemistry

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

31 Scopus citations

Abstract

A new, metal-free intermolecular formal [3 + 2] heterocyclization between triethylammonium thiolates and aryl hydrazines has been established by using the combination of I₂ and O₂ as efficient oxidation sources, allowing a concise and low-cost access to new densely functionalized 1,2,3-thiadiazoles with good to excellent yields. The reaction showed a broad scope of substrates of both reactants and attractive characteristics consisting of eco-friendly oxidants, flexible structural modification, broad functional group compatibility, and mild reaction conditions.

Original language	English
Pages (from-to)	1258-1261
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	6
DOIs	https://doi.org/10.1021/acs.orglett.6b00079
State	Published - Mar 18 2016

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abstract = "A new, metal-free intermolecular formal [3 + 2] heterocyclization between triethylammonium thiolates and aryl hydrazines has been established by using the combination of I2 and O2 as efficient oxidation sources, allowing a concise and low-cost access to new densely functionalized 1,2,3-thiadiazoles with good to excellent yields. The reaction showed a broad scope of substrates of both reactants and attractive characteristics consisting of eco-friendly oxidants, flexible structural modification, broad functional group compatibility, and mild reaction conditions.",

author = "Wei Fan and Qun Li and Yanrong Li and Hao Sun and Bo Jiang and Guigen Li",

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T1 - I2/O2-Enabled N-S Bond Formation to Access Functionalized 1,2,3-Thiadiazoles

AU - Fan, Wei

AU - Li, Qun

AU - Li, Yanrong

AU - Sun, Hao

AU - Jiang, Bo

AU - Li, Guigen

PY - 2016/3/18

Y1 - 2016/3/18

N2 - A new, metal-free intermolecular formal [3 + 2] heterocyclization between triethylammonium thiolates and aryl hydrazines has been established by using the combination of I2 and O2 as efficient oxidation sources, allowing a concise and low-cost access to new densely functionalized 1,2,3-thiadiazoles with good to excellent yields. The reaction showed a broad scope of substrates of both reactants and attractive characteristics consisting of eco-friendly oxidants, flexible structural modification, broad functional group compatibility, and mild reaction conditions.

AB - A new, metal-free intermolecular formal [3 + 2] heterocyclization between triethylammonium thiolates and aryl hydrazines has been established by using the combination of I2 and O2 as efficient oxidation sources, allowing a concise and low-cost access to new densely functionalized 1,2,3-thiadiazoles with good to excellent yields. The reaction showed a broad scope of substrates of both reactants and attractive characteristics consisting of eco-friendly oxidants, flexible structural modification, broad functional group compatibility, and mild reaction conditions.

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JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 6

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I₂/O₂-Enabled N-S Bond Formation to Access Functionalized 1,2,3-Thiadiazoles

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