Synthesis Of Nitrogenous Compounds Using Tertiary Amine As Ammonia Source

Organonitrogen compounds are a kind of important functional compounds,which are widely used in medicines,agricultural chemicals,matrials,synthesis,catalysis and other fields.Therefore,efficient synthesis of these compounds is always one of central tasks for synthetic chemists.At present,primary and secondary amines are the main ammunia sourse for their synthesis.However,primary and secondary amines are reactive,leading to the untolerance of some functional groups like aldehydes and ketones.Tertiary amines are stable and cheap,so the synthesis of nitrogen-containing organic compounds with tertiary amines as nitrogen source has attracted extensive attention of researchers.In this paper,organonitrogen compounds using tertiary amines as the ammunia sourse through N-acylation and difunctionalization of alkenes were synthesised.The specific research contents come as follows:?1?Palladium-catalyzed N-caylation of tertiary amines with carboxylic acids forming amides.Catalyzed by Pd?OAc?₂/TFP,the reaction was conducted in toluene at 120 ^oC for15 h using Piv₂O as the in situ activating reagent of carboxylic acids.This reaction showed a wide substrate scope.Both aromatic and aliphatic acids served well as the acylating reagents and coupled with tertiary amines to produce the corresponding amides in good to excellent yields.With the strategy,bioactive carboxylic acids were also efficiently modified,highlighting its potential application value in organic synthesis.?2?Palladium-catalyzed difunctionalization of alkenes with carboxylic acids and tertiary amines forming organonitrogen compounds.With the use of Piv₂O as the in situ activating reagent and Pd₂?dba?₃/X-Phos as the catalyst,1-naphthalene carboxylic acid,triethylamine and norbornene were heated in toluene at 150 ^oC for 15 h,a novel organonitrogen compound was generated in good yield through carboacylation reaction of carbon-carbon double bond.