Additions of thiols to acetylenic sulfones

Cyclizations and cycloadditions of acetylenic sulfones on solid supports.

Acetylenic sulfones attached to solid supports by means of ester linkers were employed in a variety of cyclization and cycloaddition reactions, followed by cleavage of the products from the resin by ester hydrolysis or reductive desulfonylation.

Asymmetric ruthenium-catalyzed 1,4-additions of aryl thiols to enones.

Well defined, stable, one-point binding ruthenium complexes and selectively bind and activate alpha,beta-unsaturated carbonyl compounds for cycloaddition reactions. These mild Lewis acids catalyze asymmetric 1,4-addition reactions of aryl thiols to enones with product selectivities up to 87% ee. (31)P NMR experiments provide an insight into the intricate equilibria governing the reaction mechan...

Metal-free Oxidative Coupling of Aromatic Alkenes with Thiols Leading to (E)-Vinyl Sulfones.

A facile I2O5-mediated direct oxidative coupling of aromatic alkenes with thiols toward vinyl sulfones has been developed under metal-free conditions. This methodology provides a convenient and efficient approach to various (E)-vinyl sulfones from readily available starting materials with excellent regioselectivity. The present oxidative coupling reaction, not only expands the scope of function...

Perfluoroalkanesulfonamide organocatalysts for asymmetric conjugate additions of branched aldehydes to vinyl sulfones.

Asymmetric conjugate additions of branched aldehydes to vinyl sulfones promoted by sulfonamide organocatalyst 6 or 7 have been developed, allowing facile synthesis of the corresponding adducts with all-carbon quaternary stereocenters in excellent yields with up to 95% ee.

Selective, Radical-Mediated Additions of Thiols to Alkenes in the Presence of Protected Alkynes