644-32-6Relevant articles and documents
Bloch
, p. 1342 (1937)
Moness,Lott,Christiansen
, p. 397,401 (1936)
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Westlake,Dougherty
, p. 1861 (1945)
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Transformation of Thioacids into Carboxylic Acids via a Visible-Light-Promoted Atomic Substitution Process
Fu, Qiang,Liang, Fu-Shun,Lou, Da-Wei,Pan, Gao-Feng,Wang, Rui,Wu, Min,Xie, Kai-Jun
supporting information, p. 2020 - 2024 (2022/03/31)
A visible-light-promoted atomic substitution reaction for transforming thiocacids into carboxylic acids with dimethyl sulfoxide (DMSO) as the oxygen source has been developed, affording various alkyl and aryl carboxylic acids in over 90% yields. The atomic substitution process proceeds smoothly through the photochemical reactivity of the formed hydrogen-bonding adduct between thioacids and DMSO. A DMSO-involved proton-coupled electron transfer (PCET) and the simultaneous generation of thiyl and hydroxyl radicals are proposed to be key steps for realizing the transformation.
Amide Synthesis from Thiocarboxylic Acids and Amines by Spontaneous Reaction and Electrosynthesis
Tang, Li,Matuska, Jack H.,Huang, Yu-Han,He, Yan-Hong,Guan, Zhi
, p. 2570 - 2575 (2019/06/13)
Amide bond formation is one of the most important basic reactions in chemistry. A catalyst-free approach for constructing amide bonds from thiocarboxylic acids and amines was developed. The mechanistic studies showed that the disulfide was the key intermediate for this amide synthesis. Thiobenzoic acids could be automatically oxidized to disulfides in air, thioaliphatic acids could be electro-oxidized to disulfides, and the resulting disulfides reacted with amines to give the corresponding amides. By this method, various amides could be easily synthesized in excellent yields without using any catalyst or activator. The successful synthesis of bioactive compounds also highlights the synthetic utility of this strategy in medicinal chemistry.
Visible light driven amide synthesis in water at room temperature from Thioacid and amine using CdS nanoparticles as heterogeneous Photocatalyst
Das, Sudipto,Ray, Shounak,Ghosh, Abhisek Brata,Samanta, Partha Kumar,Samanta, Suvendu,Adhikary, Bibhutosh,Biswas, Papu
, (2017/12/28)
Highly efficient photocatalytic thioacid mediated amide synthesis at room temperature using CdS nanoparticles as photocatalyst was observed under a household 30?W CFL in water. The operationally mild reaction was tolerant to a number of functional group substitutions on amine and could be scaled up to gram. This heterogeneous photocatalyst was extremely stable and could easily be recovered by simple centrifugation for at least six recycling reactions without any significant loss of catalytic performance. The possible reaction mechanism for the photocatalytic thioacid mediated amide synthesis over the CdS semiconductor has also been proposed on the basis of experimental observations.
