400828-03-7Relevant articles and documents
Dual platinum and pyrrolidine catalysis in the direct alkylation of allylic alcohols: Selective synthesis of monoallylation products
Shibuya, Ryozo,Lin, Lu,Nakahara, Yasuhito,Mashima, Kazushi,Ohshima, Takashi
supporting information, p. 4377 - 4381 (2014/05/06)
A dual platinum- and pyrrolidine-catalyzed direct allylic alkylation of allylic alcohols with various active methylene compounds to produce products with high monoallylation selectivity was developed. The use of pyrrolidine and acetic acid was essential, not only for preventing undesirable side reactions, but also for obtaining high monoallylation selectivity. Two cats are better than one: The combined use of platinum and pyrrolidine catalysts enabled the direct alkylation of allylic alcohols with reactive methylene compounds. Pyrrolidine was essential for obtaining high selectivity of the monoallylation products, which were produced without the use of excess nucleophiles. cod=1,5- cyclooctadiene, EWG=electron-withdrawing group.
Solvent-controlled highly selective bis-and monoallylation of active methylene compounds by allyl acetate with palladium(0) nanoparticle
Ranu, Brindaban C.,Chattopadhyay, Kalicharan,Adak, Laksmikanta
, p. 4595 - 4598 (2008/03/12)
(Chemical Equation Presented) Palladium(0) nanoparticle has been used as an efficient catalyst for the allylation of active methylene compounds. Very efficient bisallylation is achieved for a variety of active methylene compounds by allyl acetate and its derivatives in one stroke in THF solvent. The reaction in water provides monoallylated product selectively by allyl acetate only. The recovered Pd(0) nanoparticle is recycled. A probable mechanism is suggested.
(π-Allyl)palladium complexes bearing diphosphinidenecyclobutene ligands (DPCB): Highly active catalysts for direct conversion of allylic alcohols
Ozawa, Fumiyuki,Okamoto, Hideyuki,Kawagishi, Seiji,Yamamoto, Shogo,Minami, Tatsuya,Yoshifuji, Masaaki
, p. 10968 - 10969 (2007/10/03)
The (π-allyl)palladium complex bearing an sp2-hybridized phosphorus ligand (DPCB-OMe: 1,2-bis(4-methoxyphenyl)-3,4-bis[(2,4,6-tri-tert-butylphenyl)phosphinidene]cyclobutene) efficiently catalyzes direct conversion of allylic alcohols in the absence of activating agents of alcohols such as Lewis acids. N-Allylation of aniline proceeds at room temperature to afford monoallylated anilines in 90-97% yields. C-Allylation of active methylene compounds is also successful at 50 °C using a catalytic amount of pyridine as a base, giving monoallylation products in 85-95% yields. The catalytic mechanism involving hydrido- and (π-allyl)palladium intermediates has been proposed on the basis of stoichiometric examinations using model compounds of presumed intermediates. Copyright
Solvent-free synthesis of 4,4-bis-functionalized-1,6-dienes and 1,6-diynes on the surface of neutral alumina
Bhar, Sanjay,Kumar Chaudhuri, Subrata,Gopal Sahu, Santi,Panja, Chiradeep
, p. 9011 - 9016 (2007/10/03)
An improved procedure has been developed for the synthesis of structurally varied 4,4-bis-functionalized-1,6-dienes and 1,6-diynes through regioselective alkylation of active methylene compounds with several unsymmetrical allyl bromides and propargyl brom
Palladium(0)-Catalyzed Substitution of Allylic Substrates in an Aqueous-Organic Medium
Blart, Errol,Genet, Jean Pierre,Safi, Mohamed,Savignac, Monique,Sinou, Denis
, p. 505 - 514 (2007/10/02)
A palladium(0)-water soluble catalyst prepared in situ from palladium acetate and the sulfonated triphenyl phosphine P(C6H4-m-SO3Na)3 (or tppts) is an efficient catalyst for allylic substitution with various carbon and heteronucleophiles in an aqueous-organic medium, allowing a very easy separation of the product(s) and the recycling of the catalyst.
