Synthesis of (E)-β-iodo vinylsulfones via iodine-promoted iodosulfonylation of alkynes with sodium sulfinates in an aqueous medium at room temperature

Abstract

An efficient and facile molecular iodine-promoted method for the synthesis of (E)-β-iodo vinylsulfones with high regio- and stereoselectivity using water as the solvent at room temperature is presented.

Pd‐Catalyzed Annulation of β‐Iodovinyl Sulfones with 2‐Halophenols: A General Route for the Synthesis of 3‐Sulfonyl Benzofuran Derivatives

“…Thus, it was assumed the coordination of palladium to alkene moiety through π‐system complexation may allow partial isomerization ( Z to E ) (see the Supporting Information) . Moreover, the reaction between alkynyl sulfone ( 7 ) and 2‐bromophenol 2 a under the same conditions, unsuccessful to provide 3 a or 3 aa (Scheme d). Further, we have successfully prepared the desired deuterated starting material 1 a – D (98%‐ d ) to perform isotopic experiments (see the Supporting Information).…”

Oxidative β-C–H sulfonylation of cyclic amines

“… 6 Recent methods for the preparation of sulfones have focused on the utilization of higher valent sulfur reagents in order to avoid oxidative transformations. 7 Sulfinate salts have been employed for the direct formation of vinyl and aryl sulfones, 8 and methods based on the trapping of sulfur dioxide have also been exploited. 9 The varied methods available for sulfone preparation, together with their proven worth in medicinal chemistry, make them ideal functional groups to install using a C–H functionalization approach.…”

NaI‐Catalyzed Oxidative Amination of Aromatic Sodium Sulfinates: Synergetic Effect of Ethylene Dibromide and Air as Oxidants

“…Molecular iodine was recognized as a transition metal surrogate to catalyze, or as a selective environmentally friendly oxidant, to perform a wide range of coupling reactions of sodium sulfinates with, e.g. imidazopyridines, alkynes, cinnamic acids, 1,3‐dicarbonyl compounds, enol acetates, benzotriazoles and NH‐1,2,3‐triazoles etc. Recently, Yotphan et al disclosed an efficient iodine‐catalyzed, sodium percarbonate participated oxidative amination of sodium sulfinates whereby sulfonamides were prepared in good yields.…”