Acid chlorides coupling reactions

As outlined in Scheme 28, the synthesis of the P-ketophosphonate 131 began with a one-pot anh -aldol/reduction step between ethyl ketone 101 and aldehyde 133, giving the 1,3-syn diol 134 (>30 ldr) [130, 132-136, 145, 146], The diol 134 was then converted into the carboxylic acid 135 in six steps. Completion of the subunit 131 required conversion into the acid chloride and reaction with the lithium anion of methyl-(di-l,l,l-trifluoroethyl)-phosphonate. The C9-C24 aldehyde 132 was prepared in two steps from 136, an intermediate from previous routes [55-58], The Still-Gennari-type coupling of 131 and 132 was readily achieved via treatment with... 

Arisawa, M., Torisawa, Y., Kawahara, M., Yamanaka, M., Nishida, A., and Nakagawa, M. 1997. Lewis acid-promoted coupling reactions of acid chlorides with organoaluminum and organozinc reagents. J Org Chem 62, 4327-4329. 

Pigment Red 144 [5280-784] 20735 disa2o condensation coupling of dia2oti2ed 2,5-dichloroaniline with 3-hydroxy-2-napthoic acid, foUowed by acid chloride formation and reaction with 2-chloro-/)-phen5iene- diamine... 

The yellow members of this pigment class are obtained by coupling a dia2oti2ed aminoben2oic acid with a bisacetoacetaryUde, followed by conversion to a diacid chloride and reaction with a substituted aromatic amine. An example is Pigment Yellow 93 [5580-57-4] (Fig. 2b). 

Other disazo dyes with good substantivity and high wet-fastness properties on polyamides are Acid Red 114 (40), made by coupling o-toHdine to phenol which is then coupled to G-acid, followed by reaction of the phenoHc hydroxyl group with -toluenesulfonyl chloride, and Acid Blue 113 (41) (metanilic acid — 1-naphthylamine — 8-anilino-1-naphthalenesulfonic acid). 

Claisen ester condensation, 6, 279 Thiazolecarboxylic acid chlorides reactions, 6, 279-280 Thiazolecarboxylic acid hydrazides synthesis, 6, 280 Thiazolecarboxylic acids acidity, 6, 279 decarboxylation, 6, 279 reactions, S, 92 6, 274 Thiazole-2-carboxylic acids decarboxylation, S, 92 Thiazole-4-carboxylic acids stability, S, 92 Thiazole-5-carboxylic acids decarboxylation, S, 92 Thiazole-4,5-dicarboxylic acid, 2-amino-diethyl ester reduction, 6, 279 Thiazole-4,5-dicarboxylic acids diethyl ester saponification, 6, 279 Thiazolediones diazo coupling, 5, 59 Thiazoles, 6, 235-331 ab initio calculations, 6, 236 acidity, S, 49 acylation, 6, 256 alkylation, S, 58, 73 6, 253, 256 analytical uses, 6, 328 antifogging agents... 

Diphenylbutadiene has been obtained from phenylacetic acid and cinnamaldehyde with lead oxide, by the dehydrogenation of l,4-diphenyl-2-butene with butyllithium, and by the coupling reaction of benzenediazonium chloride and cinnamyl-ideneacetic acid." The present method gives better yields than those previously reported, is adaptable to the preparation of a variety of substituted bistyryls, and is relatively easy to carry out. 

Aryl perfluoroalkylsulfonaies, readily available by the reaction of the corresponding phenols and acid anhydrides or chlorides, are used as reagents in or-ganometallic coupling reactions (for a recent review, see reference 69)... 

NMR studies on graphite-phosphoric acid showed simultaneous, motional narrowing of both H and resonances above 225 K, indicating high mobility of phosphoric acid in the compound (FS). Chloro-sulfonic acid is inserted alone into graphite in the presence of many inorganic chlorides. The reaction temperature and stage seem to be related to the redox potential of the M"+-M couple (M3). 

FuNn iONAL Group Tolerance of PdildbrO VIMes.HCI Catalyzed Suzuki Cross-Coupling Reactions of Aryl Chlorides with Phenyi.boronic Acid Derivatives... 

Particularly, some newly developed drags, which incorporate the N-acyl sulfonamide moiety [8-10], are synthesized from the parent sulfonamides, by their coupling with acid chlorides or carboxylic anhydrides in basic conditions [11-15]. Unfortunately all these methods lead to substantial waste products. Less common reports mentioning this transformation under acidic conditions (Bronsted or Lewis acids) do not systematically examine the purpose and limitations of the reaction [16]. 

To test this hypothesis, the picolinamide 22 was prepared using in situ activated picolinic acid (Scheme 8.12). The in situ activation of picohnic acid was used because picolinyl chloride (available commercially as the HC1 salt) is relatively expensive. The coupling reaction was not straightforward, and the best results were obtained by adding 1.4equiv of thionyl chloride to a solution of 1.4equiv of picolinic acid in acetonitrile, followed by addition of triethylamine. As soon as the addition of triethylamine was complete, aniline 5 was introduced immediately because the activated picolinic acid was unstable in the presence of triethylamine. 

A palladium catalyst with a less electron-rich ligand, 2,2-dipyridyl-methylamine-based palladium complexes (4.2), is effective for coupling of aryl iodides or bromides with terminal alkynes in the presence of pyrrolidine and tetrabutylammonium acetate (TBAB) at 100°C in water.37 However, the reactions were shown to be faster in NMP solvent than in water under the reaction conditions. Palladium-phosphinous acid (POPd) was also reported as an effective catalyst for the Sonogashira cross-coupling reaction of aryl alkynes with aryl iodides, bromides, or chlorides in water (Eq. 4.18).38... 

The generated palladium chlorides possessing phosphinous acid ligands were found to be remarkably active and efficient catalysts in the presence of bases for a variety of cross-coupling reactions of aryl halides with aiylboronic... 

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