Acid chlorides copper-mediated coupling

Typical Generation of Organozinc Halides from Organic Halides and Active Zinc and Their Copper-Mediated Coupling with Acid Chlorides... 

Abstract This review covers the recent recyclable protocols for the C-N bond forming reactions between aromatic, heterocyclic and aliphatic amines such as imidazoles, benzimidazoles, benzylamines, piperidine, pyrrole, imides, anilines, hexyl, cyclohexyl amines, and amides as coupling partners with aryl iodides, bromides, chlorides, and arylboronic acids employing copper-mediated systems. The physical properties and characterization of the catalysts and their use in organic synthesis will be outlined. Most importantly, these recyclable versions developed by many groups in the recent years are potential candidates for commercial exploitation. The effect of additives, solvents, temperature, base, the nature of aryl halides on reactivity, and recycle studies of the heterogeneous catalysts are included in this... 

We have found that alkynylsilanes are smoothly converted into alkynylcopper compounds by treatment with CuCl in l,3-dimethyl-2-imidazohdinone (DMI) the copper reagents can be isolated in good yields [563]. This study was the first example of preparation and isolation of organocopper compounds by use of organosilicon reagents. The Si-Cu transmetalation is applicable to the synthesis of alkynyl ketones by Cu-catalyzed alkynylation of acid chlorides (Scheme 10.217). We have also shown that a Cu-mediated system is effective in the cross-coupling reaction between arylsilanes or heteroarylsilanes and aryl hahdes [564]. 

Although the addition of HOBT to the carbodiimide-mediated coupling of amino acids has been shown to suppress epimerization of the chiral centres present, there are still a number of cases where the level of epimerization is unsatisfactory. One method for further suppressing epimerization is to add Copperill) Chloride to the reaction system. In this case it is important that the correct stochiometry is determined, since the copper(II) chloride not only suppresses epimerization, but it also slows down the reaction rate and reduces the overall yield (eq 3). 

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