An Efficient Synthesis of Vinyl Sulfones from Alkenes and Aryl Sulfinates¹

Abstract

Vinyl sulfones have been efficiently synthesized by treatment of alkenes with sodium arene sulfinates using potassium iodide and sodium periodate in the presence of a catalytic amount of acetic acid at room temperature. The products are formed in high yields (87-95%) within 2.5-8 hours.

Regioselective Synthesis of Arylsulfonyl Benzophenones via Aerobic Oxidative [3+3] Benzannulation Reactions

“…The former ( 6 ) is accessible from homoallyl alcohol 7 via oxidative sulfonylation (iodosulfonylation of the terminal alkene and subsequent dehydroiodination) mediated by the combination of sodium arene sulfinate, potassium iodide and sodium periodate. [ 16 ] A number of homoallyl alcohols 6 are, in turn, readily prepared by the Grignard allylation of aldehydes. [ 17 ] Pleasingly, a number of variously substituted aryl, heteroaryl and alkyl ketones could be generated conveniently via this route as shown in Table 1.…”

Dihydroquinazolinones via A3‐Type Reactions of N‐Carbamoyliminium Ions

“…[16][17][18] Several variants of the A 3 coupling have been developed, [16,17] however,e xamplesw here the amine reaction partner has been replaced by other nitrogen nucleophiles are scarce. [19][20][21][22][23] To the best of our knowledge the present results provides the first examples of using urea fort he condensation as an amine surrogate in the A 3 reaction. While A 3 reactions are commonly conducted under homogeneous reactionc onditions, [16,17] af ew examples of solid-phase synthesish ave also been reported.…”

Oxidative Sulfonylation of Multiple Carbon‐Carbon bonds with Sulfonyl Hydrazides, Sulfinic Acids and their Salts

“…For the synthesis of vinyl sulfones from alkenes and sodium sulfinates, the KI/NaIO 4 system was also used. [10] Applying KI/TBHP system, alkenes 7 were sulfonylated with sulfonyl hydrazides 8 in DMSOÀ AcOH. [11] Both aromatic and aliphatic alkenes 7 and sulfonyl hydrazides 8 successfully entered the process (Scheme 4).…”