Nickel-catalyzed C-F/N-H Alkyne Annulation of Anilines: The Synthesis of Indole Derivatives via C-F Bond Activation

The reaction of N-pyrimidinyl aniline derivatives with internal alkynes in the presence of a catalytic amount of a Ni(0) complex results in the alkyne annulation of C-F/N-H, with the formation of indole derivatives. C-F bond activation, a key step in this reaction, is promoted by a pyrimidine directing group. The use of a base, such as NaH is required for the reaction to reach completion. The Ni(0)-catalyzed reaction of N-pyrimidinyl aniline derivatives with alkynes results in the alkyne annulation of C-F/N-H, with the formation of indole derivatives. C-F bond activation, a key step in this reaction, is promoted by a pyrimidine directing group. The use of a base, such as NaH is required for the reaction to ocurr.