Vinylene Carbonate as Latent Formylmethyl Surrogate: The Expediency of Ruthenium(II) Catalysis in Accessing Arylacetaldehydes, Arylacetates and Acetals

Abstract

AbstractArylacetaldehydes and its corresponding esters are fundamental structural motifs widespread in natural products and pharmaceuticals. Herein, we developed a ruthenium(II)‐catalyzed direct formylmethylation and sequential dehydrogenative esterification of phthalazinones by adopting vinylene carbonate as a C2 synthon (formylmethyl equivalent). The reaction is compatible with a repertoire of substrates bearing both electron‐donating and electron‐withdrawing substituents. Strikingly, the products obtained are governed by the additive used. A number of control experiments are conducted to elucidate the reaction mechanism. Furthermore, an important highlight is confirmation of possible intermediates by mass spectrometry.