72045-17-1Relevant academic research and scientific papers
Water-Soluble Pd-Imidate Complexes: Broadly Applicable Catalysts for the Synthesis of Chemically Modified Nucleosides via Pd-Catalyzed Cross-Coupling
Gayakhe, Vijay,Ardhapure, Ajaykumar,Kapdi, Anant R.,Sanghvi, Yogesh S.,Serrano, Jose Luis,García, Luis,Pérez, Jose,García, Joaquím,Sánchez, Gregorio,Fischer, Christian,Schulzke, Carola
, p. 2713 - 2729 (2016/04/26)
(Figure Presented) A broadly applicable catalyst system consisting of water-soluble Pd-imidate complexes has been enployed for the Suzuki-Miyaura cross-coupling of four different nucleosides in water under mild conditions. The efficient nature of the catalyst system also allowed its application in developing a microwave-assisted protocol with the purpose of expediting the catalytic reaction. Preliminary mechanistic studies, assisted by catalyst poison tests and stoichiometric tests performed using an electrospray ionization spectrometer, revealed the possible presence of a homotopic catalyst system.
Aqueous-phase heck coupling of 5-iodouridine and alkenes under phosphine-free conditions
Cho, Joon Hyung,Shaughnessy, Kevin H.
supporting information; experimental part, p. 2963 - 2966 (2012/01/17)
Palladium-catalyzed Heck couplings between 5-iodouridine and alkenes were carried out in aqueous media in the presence of triethylamine under phosphine-free conditions to give the desired products in high yields. In the absence of phosphine ligand, trieth
Synthesis of 5-substituted pyrimidine nucleosides through a palladium-catalyzed cross-coupling of alkenylhalosilanes
Matsuhashi, Hayao,Hatanaka, Yasuo,Kuroboshi, Manabu,Hiyama, Tamejiro
, p. 375 - 384 (2007/10/02)
Palladium-catalyzed cross-coupling of alkenylhalosilanes with 5-iodouracil and 5-iodouridine derivatives was described. 5-Iodo-1,3-dimethyluracil coupled with alkenylfluorodimethylsilanes to give the corresponding cross-coupled products in good yield. Ful
Palladium-catalyzed alkylatiqns in aqueous media
Casalnuovo, Albert L.,Calabrese, Joseph C.
, p. 4324 - 4330 (2007/10/02)
The efficient, catalytic alkylation of biomolecules and other organic substrates in aqueous media has been demonstrated. The water-soluble Pd(0) complex Pd(PPh2(m-C6H4SO3M))3 (2: M = Na+, K+) was isolated and characterized by single-crystal X-ray diffraction. The relevant crystal data for this complex are as follows (M = K+): a = 12.618 (1) ?, b = 19.532 (2) ?, c = 24.423 (3) ?, α = 100.65 (1)°, β= 94.37 (1)°, γ = 99.10 (1)°; P1?, T = -70 °C, dc = 1.514 g/cm3, μ = 7.74 cm-1, 14423 reflections; R = 0.054, Rw = 0.053. Crystalline, air-sensitive 2 catalyzed alkylation reactions in a variety of single-phase aqueous solvent systems. Hydrophobic or hydrophilic aryl and heteroaromatic halides underwent coupling reactions with aryl or vinyl boronic acids, alkynes, an alkene, and a dialkyl phosphite. Examples of the alkylation of biomolecules in aqueous media included the coupling of alkynes with unprotected iodonucleotides, iodonucleoside, and an iodoamino acid. This approach provided an alternative, convergent synthesis of T-505, part of a family of chain-terminating nucleotide reagents used in DNA sequencing and labeling.
A Simple Synthesis of 5-(1-Alkenyl)uracil Derivatives by Palladium-Catalyzed Oxidative Coupling of Uracils With Olefins
Hirota, Kosaku,Isobe, Yoshiaki,Kitade, Yukio,Maki, Yoshifumi
, p. 495 - 496 (2007/10/02)
The oxidative coupling of uracil derivatives 1 with olefins, such as methyl acrylate, acrylonitrile, methyl vinyl ketone, and styrene, using one equivalent of palladium acetate leads to the corresponding 5-(1-alkenyl)uracil derivatives 2.
(E)-ALCENYL-5 DESOXY-2' URIDINES PAR COUPLAGES D'ORGANOZIRCONIENS EHTYLENIQUES AVEC L'IODO-5 O-3',5'-BIS (TRIMETHYL) DESOXYURIDINE, CATALYSES PAR COMPLEXES ORGANOPALLADIES
Vincent, Patrice,Beaucourt, Jean-Pierre,Pichat, Louis
, p. 63 - 64 (2007/10/02)
(E) 5-Alkenyl 2'-deoxyuridines are obtained with moderate to high yields by the palladium catalyzed reaction of alkenylzirconium reagents with O-3',5'-bis(trimethylsilyl) deoxyuridine in T.H.F.
