Allylamine, aryl halide reactions

Allylic amines are coupled to halides giving either allylic amines or enamines depending on the reaction condition. Reaction of steroidal dienyl triflate with Boc-diprotected allylamine affords allylamine. Use of AcOK as a base is crucial for the clean coupling[102]. The tert-allylic amine 123 reacts with an aryl halide to give the enamine 125 in DMF and allylic amine 124 in nonpolar solvents[103]. 

More recently, a microwave-promoted palladium-catalyzed aminocarbonyla-tion of (hetero)aryl halides (X = I, Br, Cl) using Mo(CO)e and allylamine as a nucleophile was also described [190, 191]. Remarkably, no side products resulting from the competing Heck reaction were detected. Importantly, this was the achievement that aminocarbonylation was realized on a larger laboratory scale (25 mmol) starting from 4-iodoanisole (Scheme 2.18). 

Palladium-catalysed reactions of allylamine derivatives with aryl halides Palladium-catalysed intramolecular aiylative cyclisation reactions of iV-Allylanilines with aryl halides to yield aziridines 44 (Z=Ph) and a similar reaction of iV-Allylacet-amides resulted in the selective formation of 5-benzyl-substituted oxazolines 45 without contamination by the corresponding aziridines 44 (Z=CH3CO) [79-82] (Scheme 12.9). 

Oshima et al. reported on a Pd-catalyzed carboamination reaction of substituted allylamines with aryl halides toward the synthesis of functionalized aziridines in... 

Hayashi S, Yorimitsu H, Oshima K (2009) Synthesis of aziridines by palladium-catalyzed reactions of allylamines with aryl and alkenyl halides evidence of a syn-carboamination pathway. Angew Chem 48 7224-7226. doi 10.1002/anie.200903178... 

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