Primary alkyl amines are highly reactive in N-nucleophilic reactions with electrophiles. However, their α-C−H bonds are unreactive towards electrophiles due to their extremely low acidity (pK_a ~57). Nonetheless, 1,8-diazafluoren-9-one (DFO) can activate primary alkyl amines by increasing the acidity of the α-amino C−H bonds by up to 10⁴⁴ times. This makes the α-amino C−H bonds acidic enough to be deprotonated under mild conditions. By combining DFO with an iridium catalyst, direct asymmetric α-C−H alkylation of NH₂-unprotected primary alkyl amines with allylic carbonates has been achieved. This reaction produces a wide range of chiral homoallylic amines with high enantiopurities. The approach has successfully switched the reactivity between primary alkyl amines and allylic carbonates from intrinsic allylic amination to the α-C−H alkylation, enabling the construction of pharmaceutically significant chiral homoallylic amines from readily available primary alkyl amines in a single step.

伯烷基胺在与亲电试剂的 N 核亲核反应中具有高度反应性。然而，由于它们的酸度极低 （pK_a ~57），它们的 α-C-H 键对亲电试剂不反应。尽管如此，1,8-二氮杂氟烯-9-酮 （DFO） 可以通过将 α-氨基 C-H 键的酸度提高多达 10⁴⁴ 倍来激活伯烷基胺。这使得 α-氨基 C-H 键具有足够的酸性，可以在温和的条件下进行去质子化。通过将 DFO 与铱催化剂结合，实现了 NH₂ 未保护的伯烷基胺与烯丙基碳酸盐的直接不对称 α-C-H 烷基化。该反应产生多种具有高对映纯度的手性均烯丙胺。该方法成功地将伯烷基胺和烯丙基碳酸盐之间的反应性从本征烯丙基胺化转变为 α-C-H 烷基化，从而能够一步从现成的伯烷基胺构建具有药学意义的手性均烯丙基胺。