ChemInform Abstract: Silver‐Catalyzed Denitrative Sulfonylation of β‐Nitrostyrenes: A Convenient Approach to (E)‐Vinyl Sulfones.

Abstract

The utilization of β‐nitrostyrenes (readily available by the Henry reaction) for a highly stereoselective, convenient, and catalytic synthesis of (E)‐vinyl sulfones at room temperature is investigated.

Denitrative Cross-Couplings of Nitrostyrenes

“…Although each proposal differs in detail, the main three characteristic steps feature in all proposals. Firstly, carbon- or heteroatom-centered radical 4 is generated in situ by various methods from precursors 6 – 33 [ 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 ]. These include a thermal homolytic cleavage of labile bonds, metal-catalyzed and photochemically initiated processes.…”

“…In 2016, Chen reported the utilization of excess of benign manganese(III) acetate to promote the reaction in DMF at elevated temperature ( Scheme 19 , method A) [ 39 ]. The same year, Yadav developed a catalytic system using silver nitrate as the catalyst and potassium persulfate as co-oxidant ( Scheme 19 , method B) [ 40 ]. The mild conditions allowed the formation of miscellaneous conjugated sulfones 3 , including the labile styryl cyclopropyl sulfone 3cj .…”

“… Synthesis of conjugated sulfones from nitrostyrenes and salts of arylsulfinic acids [ 39 , 40 , 41 ]. …”