- Two-step cyanomethylation protocol: Convenient access to functionalized aryl- and heteroarylacetonitriles
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A two-step protocol has been developed for the introduction of cyanomethylene groups to metalated aromatics through the intermediacy of substituted isoxazoles. A palladium-mediated cross-coupling reaction was used to introduce the isoxazole unit, followed by release of the cyanomethylene function under thermal or microwave-assisted conditions. The intermediate isoxazoles were shown to be amenable to further functionalization prior to deprotection of the sensitive cyanomethylene motif, allowing access to a wide range of aryl- and heteroaryl-substituted acetonitrile building blocks.
- Lindsay-Scott, Peter J.,Clarke, Aimee,Richardson, Jeffery
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supporting information
p. 476 - 479
(2015/03/05)
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- A heterogeneous palladium catalyst hybridised with a titanium dioxide photocatalyst for direct C-C bond formation between an aromatic ring and acetonitrile
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A palladium catalyst hybridised with a titanium dioxide photocatalyst can promote cyanomethylation of an aromatic ring by using acetonitrile, where the photocatalyst activates acetonitrile to form a cyanomethyl radical before the C-C bond formation using the palladium catalyst.
- Yoshida, Hisao,Fujimura, Yuki,Yuzawa, Hayato,Kumagai, Jun,Yoshida, Tomoko
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supporting information
p. 3793 - 3795
(2013/05/22)
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- Pd-catalyzed α-arylation of nitriles and esters and γ-arylation of unsaturated nitriles with TMPZnCl?LiCl
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Using TMPZnCl?LiCl as a kinetically highly active base, nitriles and esters undergo a Pd-catalyzed α-arylation under mild conditions. Remarkably, in the case of α,β- or β,γ-unsaturated nitriles, a regioselective γ-arylation or a γ-alkenylation is observed.
- Duez, Stephanie,Bernhardt, Sebastian,Heppekausen, Johannes,Fleming, Fraser F.,Knochel, Paul
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supporting information; experimental part
p. 1690 - 1693
(2011/05/06)
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- Synthesis of α-Aryl nitriles through palladium-catalyzed decarboxylative coupling of cyanoacetate salts with aryl halides and triflates
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Worth its salt: The palladium-catalyzed decarboxylative coupling of the cyanoacetate salt as well as its mono- and disubstituted derivatives with aryl chlorides, bromides, and triflates is described (see scheme). This reaction is potentially useful for the preparation of a diverse array of α-aryl nitriles and has good functional group tolerance. S-Phos=2-(2,6- dimethoxybiphenyl)dicyclohexylphosphine), Xant-Phos=4,5-bis(diphenylphosphino)- 9,9-dimethylxanthene. Copyright
- Shang, Rui,Ji, Dong-Sheng,Chu, Ling,Fu, Yao,Liu, Lei
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supporting information; experimental part
p. 4470 - 4474
(2011/06/24)
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- EP2 RECEPTOR AGONISTS
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A compound of Formula (I) or a salt, solvate and chemically protected form thereof, wherein: R5 is an optionally substituted C5-20 aryl or C4-20 alkyl group; A is selected from the group consisting of Formulae (Ai), (Aii), (Aiii) D is selected from Formulae (Di), (Dii), (Diii), (Div), (Dv) B is selected from the group consisting of Formulae (Bi), (Bii), (Biii), (Biv) (Bv).
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Page/Page column 164
(2008/06/13)
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- Chemical compounds
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Provided herein are novel and useful compounds having a tryptase inhibition activity, pharmaceutical compositions comprising such compounds, and methods treating subjects suffering from a condition, disease, or disorder that can be ameliorated by the administration of an inhibitor of tryptase, e.g., asthma and inflammatory diseases, to name only a few.
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- The Acidity of Weak Carbon Acids. Part 3. The Kinetic Acidities of Substituted Benzyl Cyanides using Secondary Aliphatic Amines and Guanidines as Bases
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The rate coefficients for the base-catalysed detritiation of a series of m-substituted benzyl cyanides in DMSO and methanol have been measured at 25.0 deg C.In DMSO the bases are a series of secondary aliphatic amines and guanidines and in methanolic methoxide.For benzyl cyanide and piperidine in DMSO, the rate coefficients for detritiation at 55.0 deg C and dedeuteration at 25.0 deg C were also measured.The kinetic isotope effect and activation parameters indicate the rate determining step to be the ionisation process.Broensted coefficients, α and δ, have been calculated from both the known pKa values of the substrates and measured pKa values of the bases in DMSO.Both indicate a transition state composed of an "advanced" carbanionic structure.There is no reactivity-selectivity relationship apparent.The results are discussed in relation to Marcus and related theories.
- Bowden, Keith,Madvi, Nighat S.,Ranson, Richard J.
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p. 2474 - 2496
(2007/10/02)
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