Multi-Component Synthesis of Rare 1,3-Dihydro-1,3-azaborinine Derivatives: Application of a Bora-Nazarov Type Reaction

The twofold hydroboration products of (Fmes)BH2.SMe2 with a series of alkynes (2-butyne, arylethynes) react with two molar equiv of 2,6-dimethylphenyl isocyanide (CN-Xyl) at 80 degrees C to give rare examples of 1,3-azaborinine derivatives. A mechanistic study revealed a reaction course involving insertion of one isonitrile followed by a bora-Nazarov type ring-closure reaction and subsequent isonitrile insertion to give the respective 1,3-dihydro-1,3-azaborinines 5.