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Vinyl and aryl Grignard reagents couple with primary alkyl halides in the presence of a catalytic amount of a copper(I) halide salt. The use of Li 2 CuCl 4 rather than simple copper(I) halide salts (CuX) improves yields of these coupling reactions. [15] (5)
A notable variant of the Huisgen 1,3-dipolar cycloaddition is the copper(I) catalyzed variant, no longer a true concerted cycloaddition, in which organic azides and terminal alkynes are united to afford 1,4-regioisomers of 1,2,3-triazoles as sole products (substitution at positions 1' and 4' as shown above). The copper(I)-catalyzed variant was ...
The coupling of 2-chlorobenzoic acid and aniline is illustrative: [4] C 6 H 5 NH 2 + ClC 6 H 4 CO 2 H + KOH → C 6 H 5 N(H)−C 6 H 4 CO 2 H + KCl + H 2 O. A typical catalyst is formed from copper(I) iodide and phenanthroline. The reaction is an alternative to the Buchwald–Hartwig amination reaction.
In addition the four copper atoms form a planar Cu 4 ring based on three-center two-electron bonds. The copper to copper bond length is 242 pm compared to 256 pm in bulk copper. In pentamesitylpentacopper a 5-membered copper ring is formed, similar to (2,4,6-trimethylphenyl)gold, and pentafluorophenylcopper is a tetramer. [9]
A typical example of classic Ullmann biaryl coupling is the conversion of ortho-chloronitrobenzene into 2,2'-dinitrobiphenyl with a copper - bronze alloy. [9] [10] 2 C 6 H 4 (NO 2)Cl + 2 Cu → (C 6 H 4 (NO 2)) 2 + 2 CuCl. The reaction has been applied to fairly elaborate substrates. Ullmann reaction
Many pharmaceutical chemists attempt to use coupling reactions early in production to minimize metal traces in the product. [8] Heterogeneous catalysts based on Pd are also well developed. [9] Copper-based catalysts are also common, especially for coupling involving heteroatom-C bonds. [10] [11]