40596-23-4

Upstream product

• 111-71-7 heptanal 
• 4392-24-9 Cinnamyl bromide 
• 55090-04-5 2-(2-methoxymethoxy-octyl)-4,5-dihydro-thiazole 
• 55090-08-9 3-methoxymethoxy-nonanal 
• 100-42-5 styrene 
• 2984-50-1 1,2-Epoxyoctane 
• 339560-88-2 ((Z)-4-Methoxymethoxy-dec-1-enyl)-benzene 

Relevant academic research and scientific papers

Palladium-Catalyzed Intermolecular Heck-Type Reaction of Epoxides

The palladium-catalyzed intermolecular Heck-type reaction of both cyclic and acyclic epoxides is reported with tolerance of typical polar groups and acidic protons. Suitable alkenes include styrenes, conjugate dienes, and some electron-deficient olefins. In reactions of aliphatic terminal epoxides, ring opening occurs selectively at terminal positions, and stereocenters of epoxides are fully retained. Mechanistic studies provide evidence for in situ conversion of epoxides to β-halohydrins, generation of alkyl radicals, and radical addition to alkenes as key steps. Cyclovoltammetric determination of reduction potentials suggests that during activation of alkyl iodides by palladium(0) complexes, inner-sphere halogen abstraction is more likely than outer-sphere single electron transfer.

Stereoselective Traceless Borylation–Allenation of Propargylic Epoxides: Dual Role of the Copper Catalyst

Chiral α-allenols are prepared with high diastereocontrol through an unprecedented and spontaneous β-oxygen elimination of an α-epoxy vinyl boronate. Stochiometric experiments and DFT calculations support a dual role of the copper catalyst, which orchestrates the hydroboration and the syn-elimination step.