1058723-53-7Relevant academic research and scientific papers
Visible-Light-Mediated Cross Dehydrogenative Coupling of Thiols with Aldehydes: Metal-Free Synthesis of Thioesters at Room Temperature
Roy, Vishal Jyoti,Sen, Partha Pratim,Raha Roy, Sudipta
, p. 16965 - 16976 (2021/11/18)
Thioesters play a crucial role in biological systems and serve as important building blocks for organic synthesis. Herein, Eosin Y and TBHP mediated photochemical cross dehydrogenative coupling (PCDC) between feedstock aldehydes and thiols has been descri
One-pot synthesis of thioesters with sodium thiosulfate as a sulfur surrogate under transition metal-free conditions
Liao, Yen-Sen,Liang, Chien-Fu
, p. 1871 - 1881 (2018/03/23)
In this paper, we report an efficient synthetic method for thioester formation from sodium thiosulfate pentahydrate, organic halides, and aryl anhydrides. In the one-pot two-step reactions developed in this study, sodium thiosulfate was used as the sulfur surrogate for acylation with anhydrides, followed by substitution with organic halides through the in situ generation of thioaroylate. Furthermore, two important organic compounds could be successfully synthesized using our developed method. The advantages of the one-pot two-step reactions are operational simplicity, structurally diverse products with 42%-90% yields, use of relatively low toxic and odourless reagents, and easy applicability to large-scale operation.
Organocatalyzed anodic oxidation of aldehydes to thioesters
Ogawa, Kelli A.,Boydston, Andrew J.
supporting information, p. 1928 - 1931 (2014/05/06)
A method has been developed for the direct conversion of aldehydes to thioesters via integration of organocatalysis and electrosynthesis. The thiazolium precatalyst was found to facilitate oxidation of thiolate anions, leading to deleterious formation of disulfide byproducts. By circumventing this competing reaction, thioesters were obtained in good-to-excellent yields for a broad range of aldehyde and thiol substrates. This approach provides an atom-efficient thioesterification that circumvents the need for stoichiometric exogenous oxidants, high cell potentials, or redox mediators.
Carbonylation of aryl chlorides with oxygen nucleophiles at atmospheric pressure. Preparation of phenyl esters as acyl transfer agents and the direct preparation of alkyl esters and carboxylic acids
Watson, Donald A.,Fan, Xuexiang,Buchwald, Stephen L.
supporting information; experimental part, p. 7096 - 7101 (2009/05/09)
(Chemical Equation Presented) A mild, functional group tolerant method of the preparation of phenyl esters from aryl chlorides via palladium-catalyzed carbonylation is described using atmospheric pressure of carbon monoxide. Phenyl esters are shown to be useful acylating agents, delivering libraries of carbonyl derivatives, including alkyl, allyl and thioesters, under very mild conditions. Direct preparation of alkyl esters and carboxylic acids is also demonstrated, providing the first method for the preparation of methyl and ethyl esters from aryl chlorides without pressured reactors.
