83587-48-8Relevant academic research and scientific papers
Olefination of carbonyl compounds through reductive coupling of alkenylboronic acids and tosylhydrazones
Perez-Aguilar, M. Carmen,Valdes, Carlos
supporting information; experimental part, p. 5953 - 5957 (2012/07/30)
The partners decide: The C-C bond-forming reductive cross-coupling of alkenylboronic acids and tosylhydrazones takes place under mild reaction conditions without the need of a metal catalyst, thus giving rise to olefination-type products (see scheme). The position of the double bond in the product is determined by the structure of the coupling partners. Copyright
Nickel catalysed coupling of allylamines and boronic acid
Trost, Barry M.,Spagnol, Michel D.
, p. 2083 - 2096 (2007/10/02)
Allylamines function as substrates for cross-coupling with boronic acids in the presence of nickel(0) catalysts rather than palladium(0) catalysts.Aryl-, vinyl- and methyl-boronic acids function well.With vinyl derivatives, E-isomers couple more efficiently than Z-isomer and both fully retain the geometrical integrity.Methylations preferably employ the boronic esters like 2-methyl-1,3,2-benzodioxaborole or 2-methyl-1,3,2-dioxaborolane rather than methylboronic acid.The stereochemistry of the reaction involves a net inversion with respect to the allylamine.The regioselectivity is a function of ligand.Generally, sterically bulky donor phosphines promote new C-C bond formation at the less substituted position.Bidentate ligands, notably 1,1'-binaphthyl-2,2'-ylbis(diphenylphosphinite) (BINAPO), promote new C-C bond formation at the more substituted allyl terminus.The amines appear to be the preferred partner compared to allyl alcohols and esters with the boronic acids and give higher stereospecificity.
