• 10.1021/ja4126609
  • Journal of the American Chemical Society
  • Volume 136
  • January 2014
  • pp 2162-2167

Photoinduced, Copper-Catalyzed Alkylation of Amides with Unactivated Secondary Alkyl Halides at Room Temperature

Coupling N-alkylation of Amides with Secondary Alkyl Halides


Yapin Wang

Emaill: ywang2@lsuhsc.edu

1) Reaction of Standard Condition
Using photo-induced (hn 254), copper- catalyzed (10% CuI), two ratio base(LiOt-Bu), CH3CN/DMF as solvents and
stirring for 24 hrs at room temperature, Amides react with inactivated second alkyl halides.
2) Results of changes from the standard conditions
Table 1 shows different conditions resulting in different outcomes.  Yields of products determined by GC (<2~ 90%).
3) Results of different amides react with different second halides under standard conditions.
They are employed by N-alkylation of different amides (aliphatic even α, β-unsaturated and aromatic amides) react with different second halides (Chlorides, Bromides, iodides). The yields of purified products show in Table 2, 3, 4.
4) Mechanisms of this reaction
According to several of the copper complex in the catalytic cycle, one of the possible pathways in Figure 2.

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