Top Picks: new discover of Di-tert-butyl(2′,4′,6′-triisopropyl-[1,1′-biphenyl]-2-yl)phosphine

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The direct conversion of C-H bonds into new C-C bonds represents a powerful approach to generate complex molecules from simple starting materials. However, a general and controllable method for the sequential conversion of a methyl group into a fully substituted carbon center remains a challenge. We report a new method for the selective and sequential replacement of three C-H bonds at the allylic position of propylene and other simple terminal alkenes with different carbon groups derived from Grignard reagents. A copper catalyst and electron-rich biaryl phosphine ligand facilitate the formation of allylic alkylation products in high branch selectivity. We also present conditions for the generation of enantioenriched allylic alkylation products in the presence of catalytic copper and a chiral phosphine ligand. With this approach, diverse and complex products with substituted carbon centers can be generated from simple and abundant feedstock chemicals.

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Reference:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

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The decomposition of arylpalladium hydroxide complexes gave the corresponding phenolic products, which may form through a C(sp2)-OH bond-forming reductive elimination either by treatment of arylpalladium halide complexes with cesium hydroxide or by heating arylpalladium hydroxide complexes. Treatment of a p-nitrophenylpalladium iodide complex possessing a tBuXPhos ligand with cesium hydroxide formed a mixture of p-nitrophenol and 4,4?-di-p-nitrobiphenyl. The reaction of a D tBPP-ligated p-nitrophenylpalladium iodide complex with cesium hydroxide gave a mixture of p-nitrophenylpalladium hydroxide complex, cesium p-nitrophenoxide, and DtBPP-bridged dinuclear Pd(0) complex. Gradual decomposition of p-nitrophenylpalladium hydroxide complex to cesium p-nitorophenoxide and a DtBPP-bridged dinuclear Pd(0) complex suggested that the C(sp2)-OH bond-forming reductive elimination took place. While an isolated p-tolylpalladium hydroxide complex gave no phenolic product upon heating, thermolysis of an isolated trifluoromethyl-substituted arylpalladium hydroxide complex enabled us to observe p-trifluoromethylphenol directly. Although an ester-substituted hydroxide complex did not form free p-methoxycarbonylphenol, its invisibility enabled us to handle the kinetic equation to estimate the rate constant k1 for reductive elimination. Polar solvents such as THF and DMF accelerated the reductive elimination with a large negative entropy of activation. Comparison of these results with those in the literature suggested direct C(sp2)-OH bond-forming reductive elimination with a concerted three-centered pathway. DFT calculations also predicted the hydrogen bond between the hydroxo ligand and the solvent molecule to stabilize the transition state.

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Reference:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

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564483-19-8, Name is Di-tert-butyl(2′,4′,6′-triisopropyl-[1,1′-biphenyl]-2-yl)phosphine, molecular formula is C29H45P, belongs to chiral-phosphine-ligands compound, is a common compound. In a patnet, once mentioned the new application about 564483-19-8, Formula: C29H45P

Due to the low intrinsic acidity of amines, palladium-catalyzed C-N cross-coupling has been plagued continuously by the necessity to employ strong, inorganic, or insoluble bases. To surmount the many practical obstacles associated with these reagents, we utilized a commercially available dialkyl triarylmonophosphine-supported palladium catalyst that facilitates a broad range of C-N coupling reactions in the presence of weak, soluble bases. The mild and general reaction conditions show extraordinary tolerance for even highly base-sensitive functional groups. Additionally, insightful heteronuclear NMR studies using 15N-labeled amine complexes provide evidence for the key acidifying effect of the cationic palladium center.

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Reference:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

More research is needed about Di-tert-butyl(2′,4′,6′-triisopropyl-[1,1′-biphenyl]-2-yl)phosphine

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The invention relates to a method for preparing 3-keto-benzofurane derivatives of the general formula: Formula (I), where R is an alkyl or aryl group, R1 is hydrogen or an alkyl or aryl group, and R2 is a substituted alkyl or phenyl group. Said preparation method involves coupling a derivative of Formula III, where X is chlorine, bromine, or iodine or a sulfonate grouping: Formula (III) with a sulfonamide derivative of the formula R?SO2?NH2 in the presence of a basic agent and a catalytic system formed of a complex between a palladium compound and a ligand.

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Reference:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Some scientific research about Di-tert-butyl(2′,4′,6′-triisopropyl-[1,1′-biphenyl]-2-yl)phosphine

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Agold-catalyzed phenol synthesis was successfully used in the synthesis of dihydroisocoumarins for the first time.Alarge number of gold(I) complexes were prepared and tested; only complexes based on the biarylphosphine motif were successful. CSIRO 2014.

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Reference:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

More research is needed about Di-tert-butyl(2′,4′,6′-triisopropyl-[1,1′-biphenyl]-2-yl)phosphine

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The present invention is directed to novel retinoid-related orphan receptor gamma (RORgamma) modulators, processes for their preparation, pharmaceutical compositions containing these modulators, and their use in the treatment of inflammatory, metabolic and autoimmune diseases mediated by RORgamma.

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Reference:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Top Picks: new discover of Di-tert-butyl(2′,4′,6′-triisopropyl-[1,1′-biphenyl]-2-yl)phosphine

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An efficient Pd-catalyzed method for C?O cross-coupling of ketoximes and chalcone oximes with activated aryl bromides and bromo-chalcones has been developed. All oxime ethers were obtained in good to excellent yields by [(pi-allyl)PdCl]2/tBuXPhos (L7) catalyst system. TrixiePhos (L11) was also found to be effective for the oxime coupling. This method offers an easy and smooth coupling of chalcone oximes with activated aryl bromides and bromo-chalcones, which has not been previously explored.

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Reference:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Some scientific research about Di-tert-butyl(2′,4′,6′-triisopropyl-[1,1′-biphenyl]-2-yl)phosphine

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In this contribution, we discuss the reactivity of different phosphanes (XPhos (1a), tBuXPhos (1b), and Mes2PEt (1c)) and tris(pentafluorophenyl)borane (and in one case, EtB(C6F 5)2) against small molecules. 1a/B(C6F 5)3, 1b/B(C6F5)3, and 1c/B(C6F5)3 split dihydrogen heterolytically to yield the phosphonium borate salts 2a, 2b, and 2c, respectively. Control experiments with D2 gave the respective deuterated phosphonium borates 2a-D2, 2b-D2, and 2c-D2. The FLP systems 1b/B(C6F5)3 and 1c/B(C 6F5)3 underwent 1,2-addition reactions with ethene, resulting in the generation of the ethylene-bridged phosphonium borates 3b and 3c. As well, the Lewis pair EtB(C6F5)2 and Mes2PEt reacted with ethene to yield the corresponding 1,2-addition product 3d. At low temperature, the FLP systems 1a/B(C 6F5)3 and 1c/B(C6F5) 3 coordinated carbon dioxide (4a, 4c). The new compounds 2a, 2b, 3b, 3c, 3d, 4a, and 4c were characterized by X-ray crystal structure analyses.

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Reference:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

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Dasabuvir (1) is an HCV polymerase inhibitor which has been developed as a part of a three-component direct-acting antiviral combination therapy. During the course of the development of the synthetic route, two novel coupling reactions were developed. First, the copper-catalyzed coupling of uracil with aryl iodides, employing picolinamide 16 as the ligand, was discovered. Later, the palladium-catalyzed sulfonamidation of aryl nonaflate 33 was developed, promoted by electron-rich palladium complexes, including the novel phosphine ligand, VincePhos (50). This made possible a convergent, highly efficient synthesis of dasabuvir that significantly reduced the mutagenic impurity burden of the process.

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Reference:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

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The first total synthesis of griseofamine A and its diastereomer, 16-epi-griseofamine A, is described over seven steps with yields of 23% and 7%, respectively. Their antibacterial activities are also disclosed for the first time. Griseofamine A exhibited in vitro activities against a panel of drug-resistant Gram-positive bacteria with minimum inhibitory concentration (MIC) values of 8-16 mug/mL. Notably, 16-epi-griseofamine A was 2-3 times more potent than griseofamine A with MIC values of 2-8 mug/mL.

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Reference:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate