Methyl fluoroalkanoate as methyl-transferring reagent. Unexpected participation of BAl2 (SN2) mechanism in the reaction of methyl 2,3,3,3-tetrafluoro-2-methoxypropanoate with amines

• Methyl 2,3,3,3-tetrafluoro-2-methoxypropanoate reacts with amines either via BAl2 to amides or via BAl2 to N-methylamines.
• The reaction pathway depends on the amine nature and the reaction condition.
• 2,3,3,3-Tetrafluoro-2-methoxypropanoate behaves as a leaving group.

In the reaction of methyl 2,3,3,3-tetrafluoro-2-methoxypropanoate with arylamines or arylmethylamines, an unexpected methyl transfer from the ester to the amine by the BAl2 (SN2) mechanism was observed leading to the corresponding N-methylamines under specific conditions. The reaction was accompanied by the formation of amides via BAc2 mechanism. The unexpected methyl transfer is highly dependent on the structure of the starting amine and is supported by the absence of solvent and high temperature.

Methyl 2,3,3,3-tetrafluoro-2-methoxypropanoate reacts with amines either by BAc2 to amides or by BAl2 to N-methylamines depending on the amine nature and reaction condition.Figure optionsDownload as PowerPoint slide