Mild and Chemoselective Thioacylation of Amines Enabled by the Nucleophilic Activation of Elemental Sulfur

A mild and chemoselective method for the thioacylation of amines using α-keto acids and elemental sulfur has been developed. The key to the success of this transformation is the nucleophilic activation of elemental sulfur by thiols such as 1-dodecanethiol. A variety of functional groups, including u...

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Published inJournal of the American Chemical Society Vol. 142; no. 18; pp. 8130 - 8135
Main Authors Saito, Masato, Murakami, Sho, Nanjo, Takeshi, Kobayashi, Yusuke, Takemoto, Yoshiji
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.05.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
THIOAMIDE
LIGATIONS
PROMOTED DECARBOXYLATIVE AMIDATION
THIOFORMAMIDES
SITE-SPECIFIC INCORPORATION
BOND
INHIBITOR
ALPHA-KETO ACIDS
EFFICIENT
ORGANOLITHIUM
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Summary:A mild and chemoselective method for the thioacylation of amines using α-keto acids and elemental sulfur has been developed. The key to the success of this transformation is the nucleophilic activation of elemental sulfur by thiols such as 1-dodecanethiol. A variety of functional groups, including unprotected hydroxyl, carboxyl, amide, sulfide, and tertiary amine moieties, are tolerated under the applied reaction conditions. To demonstrate the advantages of this method compared with conventional O–S exchange reactions using Lawesson’s reagent or P2S5, thioamide moieties were introduced site-specifically into biologically active compounds.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.0c03256