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Microsomal P 450 -Catalyzed N-Dealkylation of N , N -Dialkylanilines: Evidence for a C α −H Abstraction Mechanism

2002; American Chemical Society; Volume: 124; Issue: 9 Linguagem: Inglês

10.1021/ja011041d

1943-2984

Mehul N. Bhakta, Kandatege Wimalasena,

Catalytic C–H Functionalization Methods

The early proposal that P450-catalyzed N-dealkylation of N,N-dialkylamines proceeds through a single-electron-transfer (SET) mechanism was later challenged in favor of the Cα−H abstraction mechanism. In the present study, a series of N-alkyl-N-cyclopropyl-p-chloroaniline probes have been used to examine whether the P450-catalyzed N-dealkylations proceed through a Cα−H abstraction and/or a SET mechanism, using phenobarbital-induced rat liver microsomal P450 enzymes as a model system. While the findings are highly consistent with a Cα−H abstraction mechanism, further experimental evidence may be necessary to completely rule out the SET mechanism.