The Research On The Addition Reaction Of 1,3-dithiane With α,β-Unsaturated Ketone

Due to its unique "umpolung" property,dithiane compounds have important value in organic synthesis,and have been widely used in the construction of C-C bonds and C-S bonds.This paper reviews the reaction of organically catalyzed C-S bond formation,including sulfa-Michael addition reaction,other addition reactions,desymmetrization,α-sulfidation reaction,ring opening reaction,and thioesterification reaction.Our research group has reported the free radical coupling reaction of 1,3-dithiane with aldehydes,olefins,alkynes,alkenes and the so on.Organic sulfur compounds are widely present in pharmaceuticals and natural products,so the formation of C-S compounds is of great significance.For example,In 2013,the C.-J.Wang group catalyzed the formation of thiazide antidepressants from thiols and unsaturated esters.In this paper,the conditions of various Lewis acids,metal catalysts,solvents and reaction time were optimized,has activated the C-S bond by the addition of 1,3-dithiane and α,β-unsaturated ketones catalyzed by Fe to realize the construction of complex C-S bonds.The C-S activation method exhibits good reactivity,yielding up to 92% yield corresponding thioether-thioester derivatives under mild conditions,enabling the synthesize of valuable S-linked conjugates as well as sulfur-containing drug active molecule.