Coupling reactions of amines

The N, C -coupling reactions of primary amines with BENAs are very sensitive to steric factors in BENAs. For example, the reactions with terminal BENAs are difficult to stop at the mono-alkylation step, whereas in internal BENAs, it is very difficult to isolate the bis-coupling product. A special procedure, based on this fact, enables one to synthesize bis-oximes (460) containing various oximinoalkyl substituents at the nitrogen atom. It should be emphasized that diastereoselectivity of /V,( -coupling reactions of amines with terminal BENA is very low. 

Very recently, interesting catalytic conversion of alcohols to esters, acids, and amides by hydrogen transfer to a sacrificial acceptor was reported [64, 65]. Low turnover catalytic dehydrogenative coupling reaction of amines with alcohols to form amides with H2 liberatiOTi under basic conditions was also reported very recently [66-71]. 

Lefebvre H and Pradet A (1998) Chain-coupling reaction of amine-terminated oligomers by bis(4-monosubstituted-5(4H)oxazolinones), Macromol Chem Phys 199 815-824,... 

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