110490-05-6

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 768-60-5 4-methoxyphenylacetylen 
• 57711-77-0 (2-(4'-methoxyphenyl)ethene-1,1-diyldisulfonyl)dibenzene 
• 123-11-5 4-methoxy-benzaldehyde 
• 100-07-2 4-methoxy-benzoyl chloride 
• 14271-83-1 4-methoxybenzoyl cyanide 
• 16640-68-9 cyanomethylene triphenylphosphorane 

Relevant academic research and scientific papers

Stereoselective One-Pot Synthesis of cis-1,2-Dicyanoalkenes from 1,1-Bis(benzenesulfonyl)alkenes and KCN

An efficient synthesis of cis-1,2-dicyanoalkenes by the reaction of 1,1-bis(benzenesulfonyl)alkenes with KCN was developed. This reaction was conducted in the presence of tetrabutylammonium bromide and NH4Cl/K3PO4 under phase-transfer conditions. A series of cis-1,2-dicyanoalkenes were obtained in good to high yields. Further transformation of the obtained product allows for access to imide and dicarboxylic acid compounds.

Rh-Catalyzed Asymmetric Hydrogenation of 1,2-Dicyanoalkenes

A highly efficient enantioselective hydrogenation of 1,2-dicyanoalkenes catalyzed by the complex of rhodium and f-spiroPhos has been developed. A series of 1,2-dicyanoalkenes were successfully hydrogenated to the corresponding chiral 1,2-dicyanoalkanes under mild conditions with excellent enantioselectivities (up to 98% ee). This methodology provides efficient access to the asymmetric synthesis of chiral diamines.

Catalytic 1,2-dicyanation of alkynes by palladium(II) under aerobic conditions

A stereoselective 1,2-dicyanation of various alkynes in the presence of trimethylsilyl cyanide (TMSCN) by palladium(II) catalysis under aerobic conditions is investigated. This reaction includes two cyanation pathways, syn- and anti-cyanopalladation to alkynes that are activated by Pd(II). High syn-selectivity was observed in the reaction using terminal alkynes that have bulky substituents at a propargyl position and aliphatic internal alkynes. Furthermore, a dramatic acceleration was observed with substrates having an N-arenesulfonyl functionality at a propargyl position, this indicates that both sulfoxide and carbon-carbon triple bond act as Lewis bases to Pd(II).