Electrochemical Allylation of Imines Promoted by Single-Atomic Zinc on Nitrogen-Doped Carbon

Key words

electrochemical allylation - imines - zinc - nitrogen-doped carbon

Significance

Single-atomic zinc supported on ­nitrogen-doped carbon (Zn–N–C/HCl) was prepared by calcination of a zeolite imidazolate framework-8 (ZIF-8) followed by HCl aq treatment (eq. 1). Zn–N–C/HCl, fixed on a cathode, catalyzed the electrochemical allylation of the imines with allyl bromides to give the corresponding homoallylic amines in up to 99% yield (eq. 2). Benzaldehyde also underwent the allylation with allyl bromide in 96% yield (eq. 3).

Comment

Zinc-leaching from the cathode was suppressed to 1.2–3.5 mol% under the allylation conditions. The electrochemical allylation of benzylideneaniline with allyl bromide was also carried out under continuous-flow conditions over 50 hours, where the turnover number (TON) of Zn–N–C/HCl was 9.0 and Zn-leaching was <2 mol%.

Publikationsverlauf

Artikel online veröffentlicht:
16. August 2023