Ring-Opening α,β-Difunctionalization of Cyclopropanols with Azides Enables 4-Keto-Functionalized 1,2,3-Triazole Synthesis.

Selective C-C bond cleavage and transformation of organic small molecules to create products of increased value are one of the central goals in organic chemistry. In this study, we have developed a novel TEMPO-mediated ring-opening α,β-difunctionalization of cyclopropyl alcohols with organic azides to prepare structurally important 4-keto-1,2,3-triazoles under metal- and additive-free conditions. This protocol not only provides a straightforward and efficient method for the synthesis of 4-keto-functionalized 1,2,3-triazoles in one pot but also accomplishes the goal of constructing α,β-double C-N bonds via the ring opening of cyclopropyl alcohols for the first time.