Fig. 4: Scope of functional-group permutation.
From: Oxygen migration into carbon–carbon single bonds by photochemical oxidation
a, Left: reaction design for oxygen insertion into acyclic scaffolds. Right: reaction optimization for oxygen insertion into saturated acyclic scaffolds. b, Select scope examples for methanol trapping. c, Scope examples for trapping with larger alkyl alcohols. All reactions were run at the 0.30 mmol scale, prepared in a nitrogen-filled glovebox, and irradiated with two 427-nm Kessil lamps with a cooling fan. Diastereomeric ratios were determined by 1H NMR spectroscopy analysis of the crude mixture using CH2Br2 as an internal standard. aAlcohol substrate (1.0 equiv.), MeOH (10.0 equiv.), Cu(OTf)2 (2.5 equiv.), pyridine (3.0 equiv.), MeCN (15.0 equiv.) and CH2Cl2 (0.1 M) for 48 h bAlcohol substrate (1.0 equiv.), MeOH (20.0 equiv.), FeCl3 (5.0 equiv.), DMAP (6.0 equiv.) and MeCN (0.05 M) for 48 h cAlcohol substrate (1.0 equiv.), corresponding alcohol coupling partner (5.0 equiv.), Cu(OTf)2 (2.5 equiv.), pyridine (3.0 equiv.), MeCN (15.0 equiv.) and CH2Cl2 (0.1 M) for 48 h. dAlcohol substrate (1.0 equiv.), corresponding alcohol coupling partner (8.0 equiv.), Cu(OTf)2 (4.0 equiv.), pyridine (4.8 equiv.), MeCN (24.0 equiv.) and CH2Cl2 (0.1 M) for 48 h. DMAP, 4-dimethylaminopyridine.
