203798-11-2Relevant academic research and scientific papers
Memory and dynamics in Pd-catalyzed allylic alkylation with P,N-ligands
Johansson, Charlotte,Lloyd-Jones, Guy C.,Norrby, Per-Ola
, p. 1585 - 1592 (2010)
The memory effect, known to exert a strong influence on selectivity in some applications of the Pd-catalyzed allylic alkylation, has been investigated for a catalytic system based on a bidentate P,N-ligand. Although this system might be expected to show s
Mechanism of palladium-catalyzed allylic acetoxylation of cyclohexene
Grennberg, Helena,B?ckvall, Jan-E.
, p. 1083 - 1089 (1998)
The mechanism of the quinone-based palladium-catalyzed oxidation of cyclohexene to allylic acetate was studied under various reaction conditions with 1,2-dideuterocyclohexene (62-74% D) as the substrate. The reactions gave a 1:1 mixture of 1,2-dideutero-
Catalytic allylic C-H acetoxylation and benzoyloxylation via suggested (η3-Allyl)palladium(IV) intermediates
Pilarski, Lukasz T.,Selander, Nicklas,Boese, Dietrich,Szabo, Kalman J.
supporting information; experimental part, p. 5518 - 5521 (2010/02/28)
"Chemical Equation Presented" Palladium-catalyzed allylic acetoxylations and benzoyloxylations were carried out using iodonium salts. The reactions proceed under mild conditions with high reglo- and stereoselectivity. The catalysis can be performed under
Retention of regiochemistry of allylic esters in palladium-catalyzed allylic alkylation in the presence of a MOP ligand
Hayashi, Tamio
, p. 1681 - 1687 (2007/10/03)
In the palladium-catalyzed allylic alkylation of (E)-3-substituted-2-propenyl acetates (1), 1-substituted-2-propenyl acetates (2), and 1- or 3-deuterio-2-cyclohexenyl acetate (5), which proceeds through 1,3-unsymmetrically substituted π-allylpalladium intermediates, selective substitution at the position originally substituted with acetate was observed by use of a sterically bulky monodentate phosphine ligand, 2-(diphenylphosphino)-2'-methoxy-1,1'-binaphthyl (MeO-MOP). Studies of the structure of π-allylpalladium complexes generated by mixing [PdCl(π-cyclohexenyl)]2 with 1 or 2 equiv of MeO-MOP (L*) revealed that cationic bisphosphine complex [Pd(L*)2(π-cyclohexenyl)]+Cl- is not formed even in the presence of excess ligand but neutral monophosphine complex PdCl(L*)(π-cyclohexenyl) (11) is formed, leaving excess ligand free, and that the exchange of the coordination site of Cl and L* in 11 is much slower than that in triphenylphosphine complex PdCl(PPh3)(π-cyclohexenyl) (13). The slow exchange can rationalize the retention of regiochemistry in the allylic alkylation catalyzed by palladium/MeO-MOP complex.
PALLADIUM-CATALYZED ASYMMETRIC COUPLING REACTIONS BETWEEN ALLYLIC ACETATES AND ORGANOZINC REAGENTS. MECHANISTIC IMPLICATIONS
Fiaud, Jean-Claude,Aribi-Zouioueche, Louisa
, p. 383 - 388 (2007/10/02)
Asymmetric induction and deuterium distribution studies have provided information about the mechanism of the palladium-catalyzed coupling reaction between allylic acetates and phenylzinc chloride, namely the presence of a symmetric η3-allylic ligand in the inetrmediate, probably along with a monodentate phosphine ligand.
