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. 2018 Sep 7;8(55):31455–31464. doi: 10.1039/c8ra05459b

Screening of reaction conditions, regarding oxidant, oxidant amount, ligand, and ligand amounta.

Entry Oxidant Oxidant amount (equiv.) Ligand Ligand amount (equiv.) Yieldb (%)
1 K2S2O8 2 Pyridine 1.5 2
2 Oxygen 2 Pyridine 1.5 3
3 H2O2 2 Pyridine 1.5 3
4 CHP 2 Pyridine 1.5 3
5 TBHP/decane 2 Pyridine 1.5 3
6 TBHP/water 2 Pyridine 1.5 3
7 DTBP 2 Pyridine 1.5 3
8 TEMPO 2 Pyridine 1.5 91
9 TEMPO 0 Pyridine 1.5 0
10 TEMPO 1 Pyridine 1.5 60
11 TEMPO 1.5 Pyridine 1.5 62
12 TEMPO 2 Pyridine 1.5 91
13 TEMPO 2.5 Pyridine 1.5 93
14 TEMPO 3 Pyridine 1.5 93
15 TEMPO 2 PDCA 1.5 0
16 TEMPO 2 HMTA 1.5 0
17 TEMPO 2 Ph3P 1.5 0
18 TEMPO 2 4,4′-Dipyridine 1.5 46
19 TEMPO 2 2-Aminopyridine 1.5 47
20 TEMPO 2 PHEN 1.5 56
21 TEMPO 2 Triethylamine 1.5 63
22 TEMPO 2 TMEDA 1.5 72
23 TEMPO 2 Pyridine 1.5 91
24 TEMPO 2 Pyridine 0 32
25 TEMPO 2 Pyridine 1 62
26 TEMPO 2 Pyridine 1.5 91
27 TEMPO 2 Pyridine 2 91
28 TEMPO 2 Pyridine 2.5 91
a

Reaction conditions: 2-aminobenzylalcohol (0.2 mmol); propiophenone (0.4 mmol); Cu2(OBA)2(BPY) (10 mol%); DMF (0.5 mL); 16 h; CHP: cumyl hydroperoxide; TBHP/decane: tert-butyl hydroperoxide in decane; TBHP/water: tert-butyl hydroperoxide in water; DTBP: di-tert-butylperoxide; PDCA: 2,5-pyridinedicarboxylic acid; HMTA: hexanmethylene tetraamine; PHEN: 1,10-phenanthroline; TMEDA: tetramethylethylenediamine.

b

GC yield.