Synthesis of Aryl(di)azinylmethanes and Bis(di)azinylmethanes via Transition-Metal-Catalyzed Cross-Coupling Reactions

Abstract

Aryl(di)azinyl- and bis(di)azinylmethane motifs are important as they are found in a number of pharmaceuticals and their precursors. An exhaustive overview of transition metal-catalyzed cross-coupling reactions for their synthesis has been provided. 1<b/> Introduction 2<b/> Reaction of (Di)azinyl (Pseudo)halides with Benzyl Organometallic Reagents 2.1<i/> Organozinc Reagents – Negishi Reaction 2.2<i/> Organoindium Reagents 2.3<i/> Organoaluminum Reagents 2.4<i/> Organotin Reagents – Migita–Kosugi–Stille Reaction 2.5<i/> Organoboron Reagents – Suzuki–Miyaura Reaction 2.6<i/> (Di)azinyl Methyl Thioether Reagents 3 <b/>Reaction of (Di)azinyl Organometallic Reagents with Benzyl (Pseudo)halides 3.1<i/> Organomagnesium Reagents – Kumada Reaction 3.2<i/> Organoaluminum Reagents 3.3 <i/>Organoboron Reagents – Suzuki–Miyaura Reaction 4<b/> Reaction of (Di)azinylmethyl Halides with Aryl Organo­metallic Reagents 4.1<i/> Organoboron Reagents – Suzuki–Miyaura Reaction 5<b/> Reaction of Methyl(di)azine Reagents with Aryl Halides 5.1<i/> Pre-activation of Methyl(di)azines 5.2 <i/>In Situ Pre-activation of Methyl(di)azines 5.3<i/> Direct Arylation of Methyl(di)azines 6<b/> Reaction of (Di)azine <i>N</i>-Oxides with Benzyl (Pseudo)halides 7<b/> Conclusion