Reductive Alkylation of Aromatic Amines

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Reductive Alkylation of Aromatic Amines with Enol Ethers
Reductive Alkylation of Aromatic Amines T. Jagadeeswar Reddy,*1 Michael Leclair, Melanie Proulx
Synlett 2005, No. 4, 583–586

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Abstract: Reductive alkylation of aromatic amines with 2-methoxypropene
using 1.0 equivalent of HOAc and NaBH(OAc)3 in 1,2-
dichloroethane (DCE) at room temperature furnished N-isopropyl
amines in 50–98% yields. This method was successfully extended
to trimethylsilyl enol ethers. The mild reaction conditions provide a
new alternative procedure for the reductive amination of electron
deficient aromatic amines.

Key words: reductive alkylation, aromatic amines, 2-methoxypropene,
trimethylsilylenol ethers, sodium triacetoxyborohydride