Carbon-nitrogen cross coupling amines

Exduding the introduction, this chapter is subdivided into four main sections. The first one will concentrate on mechanistic aspects. The second part wiU provide an overview of different conditions (ligands, precatalysts, bases) reported in the Hterature to provide a guide for successful cross-coupling conditions. The third part will demonstrate the applicability of C-N couplings for various nitrogen nucleophiles and sp -carbon electrophiles. Very recent developments in C-H activation/ amination reactions will be highlighted in the fourth part. 

In 1993, Corriu et al. studied the synthesis of nitrogen-containing heterocycles from (Z)-3-(tribulylstannyl)allylamine, which was prepared by the reaction of Af-(trimethylsilyl)allylamine with 2 mol of ra-butyllithium followed by treatment with chlorotributyltin and subsequent hydrolysis. The unprotected (Z)-3-(tributylstannyl)allylamine underwent a palladium-catalyzed cross-coupling reaction with aromatic bromides affording a stereospecific preparation of substituted allylic amines with Z configuration of the carbon-carbon double bond. The reactions of o/t/zo-functionalized aryl bromides offer a one-step preparation of 7-membered nitrogen heterocycles in high yields (Scheme 4.18). 

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