Access to <i>N2</i> -Substituted (Aza)Indazoles

N2-Substituted (aza)indazoles are versatile heterocycles that commonly feature in bioactive, drug-like molecules. We report a practical one-pot method developed as part of medicinal chemistry efforts to access these from amino (aza)benzaldehydes and a wide array of amines. The key oxidative N–N bond cyclization is mediated by PhI(OAc) 2, enabling rapid access to a breadth of N2 -functionalized (aza)indazoles. This protocol can also be scaled up in batch for multigram, chromatography-free synthesis.