60975-76-0Relevant academic research and scientific papers
Transition Metal-Free Trans Hydroboration of Alkynoic Acid Derivatives: Experimental and Theoretical Studies
Fritzemeier, Russell,Gates, Ashley,Guo, Xueying,Lin, Zhenyang,Santos, Webster L.
, p. 10436 - 10444 (2018)
We report a phosphine-catalyzed trans hydroboration of alkynoate esters and amides. The reaction proceeds under mild conditions with exclusive (E)-selectivity to afford (E)-β-boryl acrylates and (E)-β-boryl acrylamides in good to excellent yields. The reaction is tolerant of a variety of functional groups and allows efficient access to novel oxaboroles as well as a pargyline derivative (MAO inhibitor). Theoretical calculations suggest an internal hydride generates a phosphonium allenoxyborane followed by the formation of a key phosphonocyclobutene intermediate that collapses in a stereoselective, rate-limiting step.
Evidence for direct hydride delivery from formic acid in transfer hydrogenation
Yu, Jinquan,Spencer, Jonathan B.
, p. 2237 - 2240 (2007/10/03)
The regioselectivity of hydrometalation in transfer hydrogenation was investigated by tracing the fate of the deuterium label in both the formyl and carboxyl positions of formic acid during the isomerization of a cis enol ether. The deuterium from the for
