1. Date:

2. Background
[12] Shono, T. & Ikeda, A. J. Am. Chem. Soc. 94, 7892–7898 (1972) [14] Masui, M., Hosomi, K., Tsuchida, K. & Ozaki, S. Chem. Pharm. Bull. 33, 4798–4802 (1985).

3. Optimization Cooxidants (NHPI, pyridine, CH3CN): air(6%)
bubbling O2 (18%)
Bz2O2(0%)
tBu2O2 (0%)
H2O2(27%)
tBuOOH(51%)
PhC(CH3)2OOH(43%)
Solvents (NHPI, tBuOOH, pyridine): CH3CN (51%)
pyridine (40%)
Acetone (56%)
CH2Cl2 (21%)
MeOH (trace)
DMF (5%)
DMSO (14%)
HFIP (0%)
EtOAc (trace)
THF (trace)
Bases
(NHPI, tBuOOH, CH3CN):
pyridine (51%)
2,6-lutidine (10%) 2,4,6-collidine (13%)
Et3N (0%)
DBU (0%)
Li2CO3 (trace)
Electrolyte
(NHPI, tBuOOH, pyridine, acetone):
LiClO4 (56%)
LiBF4 (41%)
Et4NClO4 (0%)

4. Optimization Mediators (tBuOOH, pyridine, acetone).
Optimized electrochemical parameters: Cl4NHPI (0.2 equiv.), pyridine (2 equiv.), tBuOOH (1.5 equiv.), LiClO4 (0.6 equiv.), acetone (0.16 M in substrate), reticulated vitreous carbon electrodes, 10 mA per mmol of substrate. n.d., not detected.

5. Scope of the oxidation

6. Scope of the oxidation

7. Scope of the oxidation

8. Practicality

9. PGS assessment
Process Greenness Score

10. Mechanism

11. Outlook Operational simplicity and high chemoselectivity Limitation
Promising industrial application and synthetic utilization
Limitation
Not all acyclic alkenes give very high conversion