16215-13-7

Upstream product

• 104-54-1 3-Phenylpropenol 
• 100-03-8 4-chlorobenzenesulfinic acid 
• 4335-60-8 (E)-cinnamylamine 
• 14752-66-0 sodium p-chlorobenzenesulphinate 
• 106-54-7 p-Chlorothiophenol 
• 18740-04-0 cinnamyl p-chlorophenyl sulfide 

Downstream Products

• 1076-66-0 3-phenyl-1,5-hexadiene 
• 4439-45-6 1,6-diphenyl-hexa-1,5-diene 
• 56644-04-3 (E)-1-phenyl-1,5-hexadiene 
• 74120-63-1 (E)-1,4-diphenyl-1,5-hexadiene 
• 1560-06-1 1-phenyl-2-butene 
• 3412-44-0 (1E)-1,3-diphenylpropene 

Relevant academic research and scientific papers

Reciprocal-Activation Strategy for Allylic Sulfination with Unactivated Allylic Alcohols

A reciprocal-activation strategy for allylic sulfination with unactivated allylic alcohols was developed. In this reaction, the hydrogen bond interaction between allylic alcohols and sulfinic acids allowed for reciprocal activation, which enabled a dehydrative cross-coupling process to occur under mild reaction conditions. This reaction worked in an environmentally friendly manner, yielding water as the only byproduct. A variety of allylic sulfones could be obtained in good to excellent yields with wide functional group tolerance. In gram scale reactions, allylic sulfones could be conveniently isolated in high yield by filtration.

Water-Promoted Dehydrative Tsuji–Trost Reaction of Non-Derivatized Allylic Alcohols with Sulfinic Acids

A mild, green and extra activator-free synthesis of allylic sulfones from non-derivatized allylic alcohols and sulfinic acids was developed and only the easily-available Pd(PPh3)4 was used as the catalyst. This new method could be easily scaled up to gram scale, affording the target allylic sulfones in a nearly quantitative yield with water as the sole by-product. Mechanism studies both by various NMR techniques and by theoretical calculations suggested two reaction pathways may be involved in the reaction, which are dependent on the reaction media, that is, an eight-membered ring binding species may be formed in aqueous media between allylic alcohol, sulfinic acid and water, while a six-membered ring binding species may be formed in common aprotic organic solvent between allylic alcohol and sulfinic acid. Both binding species may be accounted for the efficient activation of allylic alcohols via hydrogen bonding.

Direct substitution of primary allylic amines with sulfinate salts

The NH2 group in primary allylic amines was substituted directly by sulfinate salts with excellent regio- and stereoselectivities. In the presence of 0.1 mol % [Pd(allyl)Cl]2, 0.4 mol % 1,4- bis(diphenylphosphino)butane (dppb), and excess boric acid, a range of α-unbranched primary allylic amines were smoothly substituted with sodium sulfinates in an α-selective fashion to give structurally diverse allylic sulfones in good to excellent yields with exclusive E selectivity. Replacing dppb with 1,1′-bi-2-naphthol (BINOL) allowed unsymmetric α-chiral primary allylic amines to be transformed into the corresponding allylic sulfones in good to excellent yields with excellent retention of ee. Importantly, the reaction complements known asymmetric methods in substrate scope via its unique ability to provide α-chiral allylic sulfones with high optical purity starting from unsymmetric allylic electrophiles.

Vanadium-catalyzed enantioselective oxidation of allyl sulfides

The enantioselective oxidation of allyl sulfides with a vanadyl complex of 3,5-diiodosalicylidene tert-leucinol as a catalyst and aqueous hydrogen peroxide as an oxidant afforded chiral allyl sulfoxides with high enantioselectivities of up to 97.3% ee and moderate yields.