53316-02-2Relevant academic research and scientific papers
Direct Allylation of Active Methylene Compounds with Allylic Alcohols by Use of Palladium/Phosphine-Borane Catalyst System
Shimizu, Aika,Hirata, Goki,Onodera, Gen,Kimura, Masanari
supporting information, p. 1954 - 1960 (2018/04/11)
The C?C bond formation between active methylene compounds and allylic alcohols has been newly developed by using a palladium complex as a catalyst together with a phosphine-borane ligand. The best phosphine-borane ligand for this direct allylation has bee
Development of a One-Pot Four C-C Bond-Forming Sequence Based on Palladium/Ruthenium Tandem Catalysis
Manick, Anne-Doriane,Berhal, Farouk,Prestat, Guillaume
supporting information, p. 194 - 197 (2018/01/17)
A one-pot four C-C bond-forming sequence has been developed using two distinct transition metal complexes. The sequence entails a double Pd-catalyzed allylic alkylation followed by a Ru-catalyzed ring-closing metathesis and a Pd-catalyzed Heck coupling. The use of various active methylene nucleophiles was examined with yields up to 76% (93% per C-C bond).
Versatile CuI/Pd0 dual catalysis for the synthesis of quaternary α-allylated carbonyl compounds: Development, mechanistic investigations and scope
Nahra, Fady,Mace, Yohan,Boreux, Arnaud,Billard, Francois,Riant, Olivier
supporting information, p. 10970 - 10981 (2014/09/17)
We report herein a versatile cooperative dual catalysis reaction based on a CuI/Pd0 system. Mechanistic investigation shows that every component plays a crucial role in determining the reaction outcome. The reaction is successfully extended to various substrates; such as α,β-unsaturated ketones, malonates and coumarins. The strategy tolerates different substitution patterns and affords good yields for each family of substrates.
Ruthenium-Catalyzed One-Pot Double Allylation/Cycloisomerization of 1,3-Dicarbonyl Compounds Leading to exo-Methylenecyclopentanes
Yamamoto, Yoshihiko,Nakagai, Yu-Ichiro,Itoh, Kenji
, p. 231 - 236 (2007/10/03)
The ruthenium-catalyzed one-pot double allylation/cycloisomerization of 1,3-diketones and methyl acetoacetate gave exo-methylenecyclopentanes in moderate to good yields with high isomer selectivity. The double allylation step effectively proceeded in the presence of a RuII precatalyst, [Cp*RuCl(cod)], in 1,2-dichloroethane at 90°C. The subsequent cycloisomerization was carried out upon addition of triethylsilane as a hydride source without purification of a 1,6-diene intermediate. Detailed inspections of the reaction by 1H NMR spectroscopy disclosed that triethylsilyl methyl ether plays an important role for the conversion of a ruthenium(IV) allyl complex formed in the double allylation step into a ruthenium(II) species required for the cycloisomerization.
Palladium- and Rhodium-catalysed Cyclisation of 1,6-, 1,7- and 1,8-Dienes to Cyclopentenes and Methylenecyclopentenes. Crystal Structure of Dichloro(4,4-diacetylhepta-1,6-diene)platinum(II)
Grigg, Ronald,Malone, John F.,Mitchell, Thomas R. B.,Ramasubbu, Asnok,Scott, Ronald M.
, p. 1745 - 1754 (2007/10/02)
Hepta-1,6-dienes disubstituted at C-4 with certain carbonyl-containing groups cyclise, in good yield, to the corresponding 4,4-disubstituted 1,2-dimethylcyclopent-2-enes when treated with a catalytic amount of palladium acetate in chloroform containing hydrogen chloride.Changing the catalyst precursor to chlorotris(triphenylphosphine)rhodium(I) led to the formation of the corresponding 1-methyl-2-methylenecyclopentanes which, in turn, isomerised to 1,2-dimethylcyclopent-1-enes in ethanolic hydrogen chloride containing the rhodium complex.The effect of terminal substitution of the dienes with methyl groups was examined. 1,7- and 1,8-Dienes give rise to mixtures of five-membered ring products.Possible mechanisms for the catalytic processes are discussed.The X-ray crystal structure analysis of dichloro(4,4-diacetylhepta-1,6-diene)platinum(II) is reported.
