Cyanuric chloride-catalyzed thioacetalization for organocatalytic synthesis of thioacetals

Abstract

The thioacetalization of aromatic aldehydes has been realized with broad diversity in the presence of various thiols and thiophenols using cyanuric chloride as an organocatalyst.

Role of cyanuric chloride in organic synthesis: A concise overview

“…Liu et al, [51] developed thioacetalization of aryl aldehydes (1 mmol) using thiols /thiophenols (2 mmol) in the presence of CC organocatalyst (30 mol%) using DCM solvent at RT for 12 h. High yields (74%–99%) were obtained for 17 derivatives. The plausible mechanism involved the formation of a transition state I by the activation of the formyl group by the electrophilic C‐Cl bond of CC (Scheme 23).…”

Thioacetalation and Multi-Component Thiomethylative Friedel-Crafts Arylation Using BF3SMe2

“…Advances have also been made in the field of thioacetalation, and there have been mild catalytic methods developed. ,− However, despite being the structurally simplest thioacetal derivative, methyl dithioacetals are not found in these examples, most likely due to the highly odorous nature of methanethiol. Besides methanethiol, there are also methods utilizing dimethyldislufide − to achieve methyl dithioacetals, although an unpleasant odor is associated with this reagent as well.…”