Electrochemical Metal‐Catalyzed Azidoesterification of Alkenes

Abstract

We report an efficient and sustainable electrocatalytic approach for azidoesterification of alkenes. The reaction proceeds by electrochemical iron-catalyzed oxidation of commercially available carbazates to produce alkoxycarbonyl radicals. Upon addition across alkenes, the generated transient carboncentered radicals get trapped by azido metal complexes to furnish the alkene difunctionalization products. This mild, operationally simple protocol transforms a wide variety of alkenes into the corresponding β-azido esters in good to excellent yields, thereby providing a practical access to β-amino acid derivatives from simple and readily available starting materials.

Mn-electrocatalytic oxidative C(sp3)–H azidation of 2-oxindoles and β-keto esters and azidation–cyclization of tryptamines

“…15 c Later, Zhou's group reported an electrochemical strategy for the azidation of the benzylic C(sp 3 )–H bond without a catalyst. 15 d Although significant advancements have been achieved, in comparison with the thriving field of electrocatalytic azidation of C–C double bonds, 16 the electrocatalytic azidation of C(sp 3 )–H bonds remains a relatively less explored area. The pursuit of efficient and widely applicable electrocatalytic C(sp 3 )–H azidation is still highly desirable.…”

Electrochemical Fe-catalysed radical cyclization for the synthesis of oxindoles

“…[32][33][34][35][36][37] Herein, we would like to report an electrochemical Fe-catalysed protocol for the synthesis of 3,3-disubstituted 2-oxindoles that have ester groups for further evaluation from readily accessible N-arylacrylamides and carbazates. [38][39][40][41][42][43][44] This electrocatalytic system can be smoothly scaled up for the preparation of synthetically valuable oxindoles that are key intermediates for the synthesis of natural products (Scheme 1C).…”