Ru(II)- or Rh(III)-Catalyzed Annulation of Aromatic/Vinylic Acids with Alkylidenecyclopropanes via C-H Activation.

Abstract

An efficient and new route for the synthesis of (E)-4-benzylideneisochroman-1-ones through tandem cascade annulation of benzoic acids with alkylidenecyclopropanes using Ru(II) as a catalyst is demonstrated. It is important to note that the reaction delivers selectively E-stereoselective 4-benzylideneisochroman-1-one derivatives in moderate to good yields, which has completely diverse selectivity as compared with previous methods. Further, the annulation was explored with less-reactive β C-H activation of vinylic acids with alkylidenecyclopropanes, leading to the highly useful α-pyrone derivatives in the presence of an Rh(III) catalyst.