Synthesis of halotriazoles has been studied in the past few decades. Today, coupling reactions such as Heck, Suzuki, Sonogashira, and Stille are important tools in organic synthesis for the construction of C–C bonds. While these coupling reactions have been well utilized with simple haloarenes or halo‐olefins, now they are fast emerging on halotriazoles as well. This review summarizes the development of coupling reactions on halotriazoles, some of which are also biological relevant.
Synthesis and isolation of highly unstable azirinobenzoxazole and benzoxazines in a chemodivergent fashion from aryl azido vinylogous carbonates by simple change in transition metal acetate is described. Thermal or rhodium(II) acetate‐mediated decomposition of these azides gave dihydroazirino benzoxazole. Their nickel(II) acetate‐promoted reaction gave 4‐dihydro‐2H‐benzoxazines, whereas copper(II) acetate led to the corresponding oxidized imine derivatives. Benzaoxazine derivative could be kinetically resolved using a proline‐catalyzed Mannich reaction. The benzoxazines were rapidly elaborated to angularly fused tetracyclic systems and coumarin‐fused derivatives in a “one pot” fashion.
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