2-Position-Selective Trifluoromethylthiolation of Six-Membered Heteroaromatic Compounds

研究成果: ジャーナルへの寄稿記事

2 引用 (Scopus)

抄録

The regioselective C-H trifluoromethylthiolation of six-membered heteroaromatic compounds via nucleophilic attack of a CF3S source on the electrophilically activated six-membered heteroaromatic ring was developed. The reaction proceeds in good yield with good functional group tolerance, even on a gram-scale. The key to the successful regioselective transformation is the presence of an additive (2,4-dinitrobenzenesulfonyl chloride). The regioselective trifluoromethylthiolation of quinidine derivative is also demonstrated. Trifluoromethylthiolation, followed by S-oxidation, affords the corresponding sulfones.

元の言語英語
ジャーナルOrganic Letters
DOI
出版物ステータス出版済み - 1 1 2019

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Sulfones
Quinidine
sulfones
Functional groups
attack
Chlorides
chlorides
Derivatives
Oxidation
oxidation
rings

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

これを引用

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title = "2-Position-Selective Trifluoromethylthiolation of Six-Membered Heteroaromatic Compounds",
abstract = "The regioselective C-H trifluoromethylthiolation of six-membered heteroaromatic compounds via nucleophilic attack of a CF3S source on the electrophilically activated six-membered heteroaromatic ring was developed. The reaction proceeds in good yield with good functional group tolerance, even on a gram-scale. The key to the successful regioselective transformation is the presence of an additive (2,4-dinitrobenzenesulfonyl chloride). The regioselective trifluoromethylthiolation of quinidine derivative is also demonstrated. Trifluoromethylthiolation, followed by S-oxidation, affords the corresponding sulfones.",
author = "Ryuhei Muta and Takeru Torigoe and Yoichiro Kuninobu",
year = "2019",
month = "1",
day = "1",
doi = "10.1021/acs.orglett.9b01474",
language = "English",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",

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T1 - 2-Position-Selective Trifluoromethylthiolation of Six-Membered Heteroaromatic Compounds

AU - Muta, Ryuhei

AU - Torigoe, Takeru

AU - Kuninobu, Yoichiro

PY - 2019/1/1

Y1 - 2019/1/1

N2 - The regioselective C-H trifluoromethylthiolation of six-membered heteroaromatic compounds via nucleophilic attack of a CF3S source on the electrophilically activated six-membered heteroaromatic ring was developed. The reaction proceeds in good yield with good functional group tolerance, even on a gram-scale. The key to the successful regioselective transformation is the presence of an additive (2,4-dinitrobenzenesulfonyl chloride). The regioselective trifluoromethylthiolation of quinidine derivative is also demonstrated. Trifluoromethylthiolation, followed by S-oxidation, affords the corresponding sulfones.

AB - The regioselective C-H trifluoromethylthiolation of six-membered heteroaromatic compounds via nucleophilic attack of a CF3S source on the electrophilically activated six-membered heteroaromatic ring was developed. The reaction proceeds in good yield with good functional group tolerance, even on a gram-scale. The key to the successful regioselective transformation is the presence of an additive (2,4-dinitrobenzenesulfonyl chloride). The regioselective trifluoromethylthiolation of quinidine derivative is also demonstrated. Trifluoromethylthiolation, followed by S-oxidation, affords the corresponding sulfones.

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U2 - 10.1021/acs.orglett.9b01474

DO - 10.1021/acs.orglett.9b01474

M3 - Article

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AN - SCOPUS:85066898258

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

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