54588-90-8

Upstream product

• 1562258-07-4 C₁₆H₂₃BO₂S 
• 14476-62-1 1-Ethylthio-2-phenyl-acetylen 
• 1391948-71-2 1-ethyl-2-((4-methoxyphenyl)ethynyl)sulfane 
• 1562258-27-8 C₁₇H₂₅BO₃S 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 17336-66-2 propiophenone N-tosylhydrazone 
• 108-86-1 bromobenzene 
• 424811-46-1 N'-(1-(4-methoxyphenyl)propylidene)-4-methylbenzenesulfonohydrazide 

Relevant academic research and scientific papers

Synthesis of Alkenylboronates from N-Tosylhydrazones through Palladium-Catalyzed Carbene Migratory Insertion

The palladium-catalyzed oxidative borylation reaction of N-tosylhydrazones has been developed. The reaction features mild conditions, broad substrate scope, and good functional group tolerance. It thus represents a highly efficient and practical method for the synthesis of di-, tri-, and tetrasubstituted alkenylboronates from readily available N-tosylhydrazones. One-pot Suzuki coupling and other transformations highlight the synthetic utility of the approach. DFT calculations have revealed that palladium-carbene formation and subsequent boryl migratory insertion are the key steps in the catalytic cycle. The high stereoselectivity observed in the formation of trisubstituted alkenylboronates has been explained by distortion-interaction analysis and NBO analysis.

Synthesis of (Z)-1-thio- and (Z)-2-thio-1-alkenyl boronates via copper-catalyzed regiodivergent hydroboration of thioacetylenes: An experimental and theoretical study

A Cu-catalyzed divergent hydroboration of thioacetylenes has been achieved, providing (Z)-1-thio- or (Z)-2-thio-1-alkenyl boronates in moderate to high yields with excellent regio- and stereoselectivity, by using pinacolborane or bis(pinacolato)diboron as the hydroborating reagents, respectively. DFT calculations indicate that the sulfur atom plays a key role in determining the regioselectivity through polarizing the C-C triple bonds and participating in the HOMO orbitals. Moreover, the SR group can serve as a good leaving group, resulting in the concise synthesis of six regio- and stereoisomers of trisubstituted alkenes 5 via the iterative cross-coupling of C-B and C-S bonds. Clearly, it will be valuable for assembling stereochemically diverse trisubstituted olefins in organic synthesis.