5267-49-2

Upstream product

• 6229-07-8 N-benzylxanthone imine 
• 106-43-4 para-chlorotoluene 
• 1069136-40-8 N-(4-methylphenylmethyl)xanthone imine 
• 108-90-7 chlorobenzene 
• 100-46-9 benzylamine 
• 108-86-1 bromobenzene 
• 56542-88-2 N-(4-methylbenzyl)-1,1-diphenylmethanimine 
• 106-38-7 para-bromotoluene 
• 7699-79-8 benzhydrylidene-benzyl-amine 
• 134-84-9 4-Methylbenzophenone 
• 180399-94-4 N-(Diethoxyphosphoryl)benzylideneimine 
• 55095-21-1 phenyl-p-tolylmethylamine 

Downstream Products

• 1351866-39-1 (R)-(+)-N-[(4-methylphenyl)(phenyl)methyl]acetamide 
• 1246754-95-9 (S)-(-)-N-[(4-methylphenyl)(phenyl)methyl]acetamide 

Relevant academic research and scientific papers

Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions

Diarylmethylamines are of great interest due to their prevalence in pharmaceutical chemistry. As a result, new methods for their synthesis are in demand. Herein, we report a versatile protocol for the synthesis of diarylmethylamine derivatives involving palladium-catalyzed arylation of in situ generated 2-azaallyl anion intermediates. The 2-azaallyl anions are generated by reversible deprotonation of readily available aldimine and ketimine precursors. Importantly, the arylated aldimine and ketimine products do not undergo isomerization under the reaction conditions. Scale-up of the arylation and hydrolysis of the resulting products to furnish diarylmethylamines were also successfully performed. This journal is the Partner Organisations 2014.

Carbon-carbon bond formations at the benzylic positions of N-benzylxanthone imines and N-benzyldi-1-naphthyl ketone imine

Two N-benzyl imines are designed to allow for carbon-carbon bond formations at the aminated benzylic positions. Direct benzylic arylation reactions of N-benzylxanthone imine with aryl chlorides proceed under palladium catalysis in the presence of cesium hydroxide, yielding the corresponding benzhydrylamine derivatives. Alkylation reactions of N-benzyldi-1-naphthyl ketone imine with alkyl halides in the presence of potassium tert-butoxide afford the corresponding 1-phenylalkylamines in high yields. Conjugate addition of N-benzyldi-1-naphthyl ketone imine is also described.

Palladium-catalyzed benzylic arylation of N-benzylxanthone imine

(Chemical Equation Presented) The direct benzylic arylation of N-benzylxanthone imine with aryl chloride proceeds under palladium catalysis, yielding the corresponding coupling product. The product is readily transformed to benzhydrylamine. Taking into consideration that the imine is readily available from benzylic amine, the overall transformation represents a formal cross-coupling reaction of aryl halide with α-aminobenzyl metal.

Synthesis of α-arylalkylamines by addition of Grignard reagents to N- (diethoxyphosphoryl)aldimines

Addition of organomagnesium bromides to N-(diethoxyphosphoryl) aldimines 1 carded out in tetrahydrofuran at 20-25°C affords diethyl N-alkyl- phosphoramidates 2a-w in high yields and spectroscopic purity. Deprotection of the latent amino groups in 2 results in the formation of α-arylalkylamine hydrochlorides 3a-w.