Synthesis of nitrogen-containing molecules via transition metal-catalyzed reactions on isoxazoles, anthranils and benzoisoxazoles

Abstract

Abstract This chapter focuses on transition metal-catalyzed reactions using isoxazoles, anthranils and 1,2-benzisoxazoles. Selected topics include the use of these nitroxy aromatic species in (i) metal-catalyzed annulations of alkynes (ii) catalytic reactions with metal carbenes and (iii) catalytic aminations of aryl C H bonds. In the alkyne annulation, these aromatic species typically generate α-imino gold carbenes that can further be elaborated to form various azacyclic compounds via a suitable functionality on alkynes, whereas with metal carbenes prototypical reactivity involves their imination. For Rh(I)-catalyzed aryl C H aminations, these N O aromatic species react with Rh metalocycles to cleave their N O bond and form a Rh N bond, furnishing Ar N bond formation. The large family of azacyclic products accessible from these three reactions further highlight their synthetic utility.