Alkylation of thiols with trichloroacetimidates under neutral conditions

Brian C. Duffy; Kyle T. Howard; John D. Chisholm

doi:10.1016/j.tetlet.2014.12.042

Alkylation of thiols with trichloroacetimidates under neutral conditions

Brian C. Duffy, Kyle T. Howard, John D. Chisholm

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

21 Scopus citations

Abstract

Trichloroacetimidates are displaced with thiols to form the corresponding sulfides without the need for an added acid or base by simply heating the reactants in refluxing THF. This operationally simple procedure provides the corresponding sulfides in excellent yields with only the formation of the neutral trichloroacetamide as the side product. The imidate may also be formed in situ, allowing for a direct method for the formation of sulfides from alcohols. This reaction provides a general method for the synthesis of a variety of sulfides from inexpensive and readily available alcohol starting materials.

Original language	English (US)
Pages (from-to)	3301-3305
Number of pages	5
Journal	Tetrahedron Letters
Volume	56
Issue number	23
DOIs	https://doi.org/10.1016/j.tetlet.2014.12.042
State	Published - Jun 3 2015

Keywords

Alkylation
Substitution
Sulfide
Thiol
Trichloroacetimidate

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2014.12.042

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title = "Alkylation of thiols with trichloroacetimidates under neutral conditions",

abstract = "Trichloroacetimidates are displaced with thiols to form the corresponding sulfides without the need for an added acid or base by simply heating the reactants in refluxing THF. This operationally simple procedure provides the corresponding sulfides in excellent yields with only the formation of the neutral trichloroacetamide as the side product. The imidate may also be formed in situ, allowing for a direct method for the formation of sulfides from alcohols. This reaction provides a general method for the synthesis of a variety of sulfides from inexpensive and readily available alcohol starting materials.",

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AU - Duffy, Brian C.

AU - Howard, Kyle T.

AU - Chisholm, John D.

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Y1 - 2015/6/3

N2 - Trichloroacetimidates are displaced with thiols to form the corresponding sulfides without the need for an added acid or base by simply heating the reactants in refluxing THF. This operationally simple procedure provides the corresponding sulfides in excellent yields with only the formation of the neutral trichloroacetamide as the side product. The imidate may also be formed in situ, allowing for a direct method for the formation of sulfides from alcohols. This reaction provides a general method for the synthesis of a variety of sulfides from inexpensive and readily available alcohol starting materials.

AB - Trichloroacetimidates are displaced with thiols to form the corresponding sulfides without the need for an added acid or base by simply heating the reactants in refluxing THF. This operationally simple procedure provides the corresponding sulfides in excellent yields with only the formation of the neutral trichloroacetamide as the side product. The imidate may also be formed in situ, allowing for a direct method for the formation of sulfides from alcohols. This reaction provides a general method for the synthesis of a variety of sulfides from inexpensive and readily available alcohol starting materials.

KW - Alkylation

KW - Substitution

KW - Sulfide

KW - Thiol

KW - Trichloroacetimidate

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JO - Tetrahedron Letters

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Alkylation of thiols with trichloroacetimidates under neutral conditions

Abstract

Keywords

ASJC Scopus subject areas

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