Carbon-nitrogen cross-coupling reaction

The first examples of microwave-mediated solid-phase carbon-nitrogen cross-coupling reactions were reported in 1999 by the group of Combs [16], using a boronic... 

Copper-Catalyzed Carbon-Nitrogen Cross-Coupling Reactions... 

Jiang L, Buchwald SL (2004) Palladium-catalyzed aromatic carbon-nitrogen bond formation. In de Meijere A, Diedeiich F (eds) Metal-catalyzed cross-coupling reactions, 2nd edn. Wiley-VCH, Weinheim... 

Metal complexes as catalysts for oxygen, nitrogen and carbon-atom transfer reactions (Tsutomu Katsuki) Metal complexes as catalysts for H-X (X = B,CN, Si, N, P) addition to CC multiple bonds (M. Whittlesey) Metal complexes as catalysts for C-C cross-coupling reactions (I. Beletskaya, A.V. Cheprakov)... 

Cross-coupling reaction of aryl halides with arylamines is a straightforward method for forming a carbon-nitrogen bond and is catalyzed by a palladium complex. This methodology was applied by Kanbara, Mullen, and several groups to... 

Utility of Enol and Aryl Triflates. Enol and aryl triflates are extensively used for cross-coupling reactions, the formation of carbon-carbon, carbon-tin, carbon-nitrogen, carbon-sulfur, carbon-phosphorus, and carbon-halogen bonds, and reduction/ deoxygenation. In recent examples, they were used to form enamines or enamides or were eliminated to cyclooctynes for copper-free cycloadditions in biological systems. 

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). 

The chemistry of fluorinated 1,3,5-triazines is not as well studied as the chemistry of their chloro derivatives. In case of fluorotriazines the reactions directed on the ring nitrogen atoms, displacement of fluorine atoms and reactions on carbon atoms on the ring with retention of the fluorine atoms appear to be the most characteristic ones. In this section the N-alkylation and N-acylation reactions, as well as replacement of fluorine atoms by a variety of nucleophiles will be considered. Metallation of fluorotriazines and synthesis on the basis of organometallic compounds, as well as the cross-coupling reactions were described. Also several examples of photochemical reactions and transformations are presented. 

Paul, F., Patt, J., Hartwig, J. F. Palladium-catalyzed formation of carbon-nitrogen bonds. Reaction intermediates and catalyst improvements in the hetero cross-coupling of aryl halides and tin amides. J. Am. Chem. Soc. 1994,116, 5969-5970. 

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