Coupling reactions synthesis

S. F. Martin, Synthesis of aldehydes, ketones, and carboxylic acids from lower carbonyl compounds by C-C coupling reactions. Synthesis pp. 633-665 (1979). 

Other interests in the area of phosphorus acids and their derivatives has centered on the following subjects synthesis of new ligands and catalysts for known reactions, synthesis of supramolecular logic gates, use of phosphates as electrophiles in palladium-catalyzed cross-coupling reactions, synthesis of phosphate based dendrimers and conjugates with oligosaccharides. 

Three-Component Coupling Reaction Synthesis of (-)- and (+)-Actinoboline... 

H. Ishikawa, S. Sawano, Y. Yasui, Y. Shibata, Y Hayashi, Angew. Chem. Int. Ed. 2011, 50, 3774—3779. Asymmetric one-pot four-component coupling reaction synthesis of substituted tetrahydropyrans catalyzed by diphenylprohnol silyl ether. 

Carbonylative Coupling Reactions Synthesis of Carbonyl Derivatives... 

S. F. Martin, Synthesis of Aldehydes, Ketones and Carboxylic Acids from Lower Carbonyl Compounds by C—C Coupling Reactions , Synthesis, 1979, 633. 

Transition Metal-Catalyzed Coupling Reactions Synthesis of Aryl Amines. LHMDS was first used as a base to de-protonate alkylamines in the palladium-catalyzed synthesis of arylamines. This base is mild enough such that the alkyl-amide is generated at the transition metal center. Earlier examples reported that the reaction of an aryl bromide with cyclo-hexylamine and LHMDS in the presence of 5 mol % of (tri-o-tolylphosphine)2PdCl2 in toluene at 100 °C produced the desired arylamine in 89% yield after 2 h (eq 19). ... 

Scheme 5-112. Negishi coupling reactions synthesis of polyenes. ...

Ramana T, Sha P, Das M, Punniyamurthy T. Copper-catalyzed domino intra and intermolecular C—S cross-coupling reactions synthesis of 2-(arylthio)arylcyanamides. Org. Lett. 2010 12 84-87. 

Tappe FMJ, Trepohl VT, Oestreich M. Transition-metal-catalyzed C—P cross-coupling reactions. Synthesis 2010 18 3037-3062. 

Bushby, R.J., Lu, Z. Isopropoxy as a masked hydroxy group in aryl oxidative coupling reactions. Synthesis 2001, 763-767 (2001)... 

Oligonucleotide synthesis involves specialized blocking and coupling reactions the chemistry of which is beyond the scope of a typical introductory course The in terested reader is referred to http //WWW bi umist ac uk/ users/dberrisford/1 MBL/ nucleicacidB html... 

Another area of interest to the industrial sector is the development of a more efficient synthesis of biaryl compounds. This has been accompHshed using a Ni(II)-cataly2ed Grignard coupling reaction with an aryl haUde (86—89). 

Polymerization by G—G Goupling. An aromatic carbon—carbon coupling reaction has been employed for the synthesis of rigid rod-like polyimides from imide-containing dibromo compounds and aromatic diboronic acids ia the presence of palladium catalyst, Pd[P(CgH )2]4 (79,80). 

In the synthesis of Win 57,273 the attachment of the group, a 2,6-dimethylpytidinyl group, involves formation of a carbon-carbon bond rather than a carbon-nitrogen bond. The method for the attachment of this group is a palladium mediated coupling reaction (77,78) of 4-tributylstarmyl-2,6-dimethylpyridine [122033-61 -8] with a 7-halo quinolone (26). 

In a synthesis of decinine a phenol was protected as a methanesulfonate that was stable during an Ullman coupling reaction and during condensation, catalyzed by calcium hydroxide, of an amine with an aldehyde. Aryl methanesulfonates are cleaved by warm sodium hydroxide solution. " ... 

In general, imines are too reactive to be used to protect carbonyl groups. In a synthesis of juncusol, however, a bromo- and an iodocyclohexylimine of two identical aromatic aldehydes were coupled by an Ullman coupling reaction modi-fied by Ziegler. The imines were cleaved by acidic hydrolysis (aq. oxalic acid, THF, 20°, 1 h, 95% yield). Imines of aromatic aldehydes have also been prepared... 

Carbamates can be used as protective groups for ammo acids to minimize race-mization in peptide synthesis. Raccmi/ation occurs during the base-catalyzed coupling reaction of an W-protected, catboxyl-uc ivated amino acid, and takes place in the intermediate oxazolone that foro S readily from an N-acyl protected amino... 

The reaction shown above for the steam reforming of methatie led to die formation of a mixture of CO and H2, die so-called synthesis gas. The mixture was given this name since it can be used for the preparation of a large number of organic species with the use of an appropriate catalyst. The simplest example of this is the coupling reaction in which medrane is converted to ethane. The process occurs by the dissociative adsorption of methane on the catalyst, followed by the coupling of two methyl radicals to form ethane, which is then desorbed into the gas phase. 

The true, all-aromatic system (see 18, below) described by Kime and Norymberski is unusual in the sense that all of the ether linkages bridge aromatic carbons ". Synthesis of 18, therefore, required extensive use of copper mediated coupling reactions. As expected for such reactions, yields were generally low. The aromatics such as 18 were ineffective at binding either alkali metal or ammonium cations ". ... 

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