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Synfacts 2023; 19(09): 0909
DOI: 10.1055/s-0042-1752757
Polymer-Supported Synthesis

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

Contributor(s):
Yasuhiro Uozumi
,
Shintaro Okumura
Masuda R, Yasukawa T, *, Yamashita Y, Maki T, Yoshida T, Kobayashi S. * The University of Tokyo, Japan
Heterogeneous Single-Atom Zinc on Nitrogen-Doped Carbon Catalyzed Electrochemical Allylation of Imines.

J. Am. Chem. Soc. 2023;
145: 11939-11944
DOI: 10.1021/jacs.3c03674.
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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).


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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%.


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Publication History

Article published online:
16 August 2023

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