Na2S·9H2O Enabled Defluorodisulfuration and Hydrodefluorination of Perfluorobutyl Tetralones: Synthesis of Trifluoromethyl 1,2-Dithioles

Zi Lun Yu; Man Hang Feng; Peng Yuan Zhang; Hao Xu; Danhua Ge; Mengtao Ma; Zhi Liang Shen; Xue Qiang Chu

doi:10.1021/acs.orglett.3c01573

Na₂S·9H₂O Enabled Defluorodisulfuration and Hydrodefluorination of Perfluorobutyl Tetralones: Synthesis of Trifluoromethyl 1,2-Dithioles

Zi Lun Yu, Man Hang Feng, Peng Yuan Zhang, Hao Xu, Danhua Ge, Mengtao Ma, Zhi Liang Shen, Xue Qiang Chu

School of Chemistry and Moleculai Engineering

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

11 Scopus citations

Abstract

An unprecedented defluorocyclization of perfluorobutyl tetralones with Na2S·9H2O was developed for the synthesis of trifluoromethyl 1,2-dithioles, which provided chemists novel access to biologically and pharmaceutically relevant organofluorides. Successive C(sp3)-F bond functionalization at the perfluoroalkyl chain is vital for the formation of four C-H/C-S/S-S bonds and a five-membered S-heterocycle assembly. Cheap, weakly toxic, and odorless inorganic sulfide Na2S·9H2O acts as both a disulfurating precursor and a hydrodefluorinating reagent in this tandem multi-bond-interconverting reaction.

Original language	English
Pages (from-to)	4388-4393
Number of pages	6
Journal	Organic Letters
Volume	25
Issue number	23
DOIs	https://doi.org/10.1021/acs.orglett.3c01573
State	Published - 16 Jun 2023

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title = "Na2S·9H2O Enabled Defluorodisulfuration and Hydrodefluorination of Perfluorobutyl Tetralones: Synthesis of Trifluoromethyl 1,2-Dithioles",

abstract = "An unprecedented defluorocyclization of perfluorobutyl tetralones with Na2S·9H2O was developed for the synthesis of trifluoromethyl 1,2-dithioles, which provided chemists novel access to biologically and pharmaceutically relevant organofluorides. Successive C(sp3)-F bond functionalization at the perfluoroalkyl chain is vital for the formation of four C-H/C-S/S-S bonds and a five-membered S-heterocycle assembly. Cheap, weakly toxic, and odorless inorganic sulfide Na2S·9H2O acts as both a disulfurating precursor and a hydrodefluorinating reagent in this tandem multi-bond-interconverting reaction.",

author = "Yu, {Zi Lun} and Feng, {Man Hang} and Zhang, {Peng Yuan} and Hao Xu and Danhua Ge and Mengtao Ma and Shen, {Zhi Liang} and Chu, {Xue Qiang}",

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doi = "10.1021/acs.orglett.3c01573",

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T1 - Na2S·9H2O Enabled Defluorodisulfuration and Hydrodefluorination of Perfluorobutyl Tetralones

T2 - Synthesis of Trifluoromethyl 1,2-Dithioles

AU - Yu, Zi Lun

AU - Feng, Man Hang

AU - Zhang, Peng Yuan

AU - Xu, Hao

AU - Ge, Danhua

AU - Ma, Mengtao

AU - Shen, Zhi Liang

AU - Chu, Xue Qiang

PY - 2023/6/16

Y1 - 2023/6/16

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AB - An unprecedented defluorocyclization of perfluorobutyl tetralones with Na2S·9H2O was developed for the synthesis of trifluoromethyl 1,2-dithioles, which provided chemists novel access to biologically and pharmaceutically relevant organofluorides. Successive C(sp3)-F bond functionalization at the perfluoroalkyl chain is vital for the formation of four C-H/C-S/S-S bonds and a five-membered S-heterocycle assembly. Cheap, weakly toxic, and odorless inorganic sulfide Na2S·9H2O acts as both a disulfurating precursor and a hydrodefluorinating reagent in this tandem multi-bond-interconverting reaction.

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JF - Organic Letters

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ER -

Na₂S·9H₂O Enabled Defluorodisulfuration and Hydrodefluorination of Perfluorobutyl Tetralones: Synthesis of Trifluoromethyl 1,2-Dithioles

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