219858-15-8Relevant academic research and scientific papers
The Effect of Hydrogen Bonding on Allylic Alkylation and Isomerization Reactions in Ionic Liquids
Ross, James,Xiao, Jianliang
, p. 4900 - 4906 (2003)
Neutral allylic alkylation reactions, in which a base is generated in situ and which hence require no external bases, can significantly be retarded when carried out in the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim][BF4]). Evidence suggests that the base or base precursor enters into hydrogen bonding with the imidazolium cation and is thus made less readily available for deprotonation of pre-nucleophiles. However, the reaction proceeds well in the presence of stronger bases that are capable of deprotonation. Whilst the phenomenon of hydrogen bonding in ionic liquids can be detrimental to reactions such as allylic alkylation, it can be exploited to suppress unwanted allylic isomerization.
A new class of non-C2-symmetric ligands for oxidative and redox-neutral palladium-catalyzed asymmetric allylic alkylations of 1,3-diketones
Trost, Barry M.,Donckele, Etienne J.,Thaisrivongs, David A.,Osipov, Maksim,Masters, James T.
, p. 2776 - 2784 (2015/03/04)
We report the discovery, synthesis, and application of a new class of non-C2-symmetric phosphoramidite ligands derived from pyroglutamic acid for use in both oxidative and redox-neutral palladium-catalyzed asymmetric allylic alkylations of 1,3-diketones. The resulting chiral products are typically obtained in high yield with good to excellent levels of enantioselectivity.
Catalytic intermolecular allylic C-H alkylation
Young, Andrew J.,White, M. Christina
supporting information; experimental part, p. 14090 - 14091 (2009/03/11)
The first electrophilic Pd(II)-catalyzed allylic C-H alkylation is reported, providing a novel method for formation of sp3-sp3 C-C bonds directly from C-H bonds. A wide range of aromatic and heteroaromatic linear (E)-α-nitro-arylpent
