23837-07-2Relevant academic research and scientific papers
Visible-Light Photoredox-Catalyzed Thioacetalization of Aldehydes Under Metal-Free and Solvent-Free Conditions
Du, Kai,Wang, Shao-Chien,Basha, R. Sidick,Lee, Chin-Fa
, p. 1597 - 1605 (2019)
A first visible-light photoredox-catalyzed thioacetalization of aldehydes under metal-free and solvent-free conditions is described. Under blue LED irradiation, a reactive thiyl radical was initially generated through single-electron oxidation of thiol, w
Pot-economy autooxidative condensation of 2-Aryl-2-lithio-1,3-dithianes
Vale, Joao R.,Rimpil?inen, Tatu,Siev?nen, Elina,Rissanen, Kari,Afonso, Carlos A. M.,Candeias, Nuno R.
, p. 1948 - 1958 (2018/02/23)
The autoxidative condensation of 2-aryl-2-lithio-1,3-dithianes is here reported. Treatment of 2-aryl-1,3-dithianes with n-BuLi in the absence of any electrophile leads to condensation of three molecules of 1,3-dithianes and formation of highly functionalized α-thioether ketones orthothioesters in 51-89% yields upon air exposure. The method was further expanded to benzaldehyde dithioacetals, affording corresponding orthothioesters and α-thioether ketones in 48-97% yields. The experimental results combined with density functional theory studies support a mechanism triggered by the autoxidation of 2-aryl-2-lithio-1,3-dithianes to yield a highly reactive thioester that undergoes condensation with two other molecules of 2-aryl-2-lithio-1,3-dithiane.
