Visible-Light-Mediated Cross Dehydrogenative Coupling of Thiols with Aldehydes: Metal-Free Synthesis of Thioesters at Room Temperature

Autor:	Sudipta Raha Roy, Partha Pratim Sen, Vishal Jyoti Roy
Rok vydání:	2021
Předmět:	chemistry.chemical_classification chemistry.chemical_compound chemistry Aryl Organic Chemistry Thiol Dehydrogenation Organic synthesis Eosin Y Thioester Aldehyde Combinatorial chemistry Alkyl
Zdroj:	The Journal of Organic Chemistry. 86:16965-16976
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.1c02111
Popis:	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 described at room temperature to synthesize thioesters. This thioesterification protocol proceeds smoothly to give the desired products in good to excellent yields by the suitable PCDC of both alkyl/aryl- aldehydes with a variety of alkyl/aryl-thiols and generates water and tBuOH as green byproducts. This method is also found to be scalable with good efficiency. Mechanistic investigations reveal that under this photochemical condition, the formation of acyl radical can be achieved from aldehyde. This acyl radical was further intercepted with an intermediate disulfide, generated in situ via the dehydrogenation of thiol to give the desired thioester. Moreover, disulfides, which are relatively easier to handle, also provided good to excellent yields in the optimized reaction condition. This protocol was further extended toward the more challenging direct transformation of alcohols to thioesters.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::89cd13b257db1f24f95f78c0b6e960c5 https://doi.org/10.1021/acs.joc.1c02111 Zobrazit plný text záznamu