Unexpected Products of Benzylamine Oxidation Catalyzed by Manganese Porphyrins: Some Factors that Play a Critical Role for Imine Formation

摘要

This work describes the oxidation of benzylamine by PhIO,catalyzed by a series of first-row metal salts and the respective first-,second-,and third-generation metalloporphyrins.Five products were identified in reactions with [Mn~(III)TPPCl]/PhIO.In this system,two products obtained(benzaldehyde oxime and N-benzylbenzamide)were not previously described when [Mn~(III)TPPCl] was used as catalyst.The change in the oxidant type(PhIO,PhI(OAc)2,H2O2 or m-CPBA)modified the selectivity for the major product in the presence of [Mn~(III)TPPCl].For a second-generation manganese porphyrin,the highest total yield was observed(99%),with 72% of imine product and only 1% of catalyst destruction,even in homogeneus system.