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. Author manuscript; available in PMC: 2020 May 6.
Published in final edited form as: Angew Chem Int Ed Engl. 2019 Mar 14;58(19):6385–6390. doi: 10.1002/anie.201813960

Table 2.

Combined electrochemical/photochemical iodide-mediated process for dehydrogenative amination of imidate.[a]

graphic file with name nihms-1018758-t0008.jpg
Entry Potential/V vs Fc/Fc+ TBAI Yield/%
1 0.5 10 mol% 54%
2 0.3 10 mol% 47%
3 0.7 10 mol% 71%
4[b] 0.7 10 mol% 82% (73%)
5[b] 0.7 - n.d.
6[b,c] 0.7 10 mol% 2%
[a]

The reaction was performed on a 0.5 mmol scale under constant potential (CP) conditions, yields were determined by 1H NMR with m-xylene as an internal standard; isolated yield shown in parenthesis.

[b]

With 1 equiv of pyridine.

[c]

Without irradiation.

TFE = 2,2,2-Trifluoroethanol. n.d. = not detected.