- Water-Soluble Pd-Imidate Complexes: Broadly Applicable Catalysts for the Synthesis of Chemically Modified Nucleosides via Pd-Catalyzed Cross-Coupling
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(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.
- 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
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p. 2713 - 2729
(2016/04/26)
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- Aqueous-phase heck coupling of 5-iodouridine and alkenes under phosphine-free conditions
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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
- Cho, Joon Hyung,Shaughnessy, Kevin H.
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supporting information; experimental part
p. 2963 - 2966
(2012/01/17)
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- Synthesis of 5-substituted pyrimidine nucleosides through a palladium-catalyzed cross-coupling of alkenylhalosilanes
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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
- Matsuhashi, Hayao,Hatanaka, Yasuo,Kuroboshi, Manabu,Hiyama, Tamejiro
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p. 375 - 384
(2007/10/02)
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- Palladium-catalyzed alkylatiqns in aqueous media
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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.
- Casalnuovo, Albert L.,Calabrese, Joseph C.
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p. 4324 - 4330
(2007/10/02)
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- A Simple Synthesis of 5-(1-Alkenyl)uracil Derivatives by Palladium-Catalyzed Oxidative Coupling of Uracils With Olefins
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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.
- Hirota, Kosaku,Isobe, Yoshiaki,Kitade, Yukio,Maki, Yoshifumi
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p. 495 - 496
(2007/10/02)
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- (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
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(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.
- Vincent, Patrice,Beaucourt, Jean-Pierre,Pichat, Louis
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