69286-52-8

Upstream product

• 319925-09-2 C₈H₈ClNO₂S 
• 69052-20-6 E-cinnamyltriphenylphosphonium chloride 
• 89-98-5 2-chloro-benzaldehyde 
• 851191-43-0 (2-chlorobenzyl)zinc(II) bromide 
• 104-55-2 3-phenyl-propenal 
• 17333-83-4 2-chlorobenzenediazonium 

Relevant academic research and scientific papers

Phosphorus-recycling wittig reaction: Design and facile synthesis of a fluorous phosphine and its reusable process in the wittig reaction

This study shows that phosphorus sources can be recycled using the appropriate fluorous phosphine in the Wittig reaction. The designed fluorous phosphine, which has an ethylene spacer between its phosphorus atom and the perfluoroalkyl group, was synthesized from air-stable phosphine reagents. The synthesized phosphine can be used for the Wittig reaction process to obtain various alkenes in adequate yields and stereoselectivity. The concomitantly formed fluorous phosphine oxide was extracted from the reaction mixture using a fluorous biphasic system. The fluorous phosphine was regenerated by reducing the fluorous phosphine oxide with diisobutylaluminum hydride. Finally, a series of gram scale phosphorus recycling processes were performed, which included the Wittig reaction, separation, reduction, and reuse.

A highly tunable stereoselective olefination of semistabilized triphenylphosphonium ylides with N -Sulfonyl imines

The Wittig reaction involving direct olefination of triphenylphosphonium ylides (Ph3PCHR) with aldehydes is arguably the most often used method for alkene synthesis, but in general it yields mixtures of Z- and E-alkenes for semistabilized triphenylphosphonium ylides (R = aryl or vinyl). We have developed a simple and efficient protocol to improve the stereoselectivity significantly by replacing the aldehydes used in the Wittig reaction with N-sulfonyl imines, which possess distinct electronic and steric properties relative to aldehydes. A broad range of aromatic, α,β-unsaturated, and aliphatic imines bearing appropriate N-sulfonyl groups smoothly undergo olefination reaction with various benzylidenetriphenylphosphoranes or allylidenetriphenylphosphoranes under mild reaction conditions to afford an array of both Z- and E-isomers of conjugated alkenes in good to excellent yields and with greater than 99:1 stereoselectivity. Moreover, this tunable protocol has been successfully applied to the highly stereoselective synthesis of two anticancer agents, DMU-212 and its Z-isomer.

Palladium-catalyzed stereoselective synthesis of (E)-stilbenes via organozinc reagents and carbonyl compounds

In the presence of a catalytic amount of PdCl2(PPh 3)2 and a silylating agent, organozinc halides reacted with carbonyl compounds to give the corresponding (E)-stilbenes in good to excellent yields under mild conditions. The reaction mechanism is briefly discussed.