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. Author manuscript; available in PMC: 2023 Oct 5.
Published in final edited form as: J Am Chem Soc. 2022 Sep 22;144(39):18109–18116. doi: 10.1021/jacs.2c08332

Table 1.

Optimization of the C(sp2)─H Hydroxylation Using Hydrogen Peroxidea

graphic file with name nihms-1905791-t0005.jpg
Entry Ligand Base Solvent Yield (%)
1b L1 K2HPO4 DMA 37
2 L1 K2HPO4 DMA 0
3 L2 K2HPO4 DMA 0
4 L3 K2HPO4 DMA 0
5 L4 K2HPO4 DMA 65
6 L5 K2HPO4 DMA trace
7 L6 K2HPO4 DMA trace
8c L7 K2HPO4 DMA <5
9c L8 K2HPO4 DMA 0
10 No L K2HPO4 DMA 0
11 L4 KHCO3 DMA 80
12 L4 K2HPO4 CH3CN 86
a

Conditions: 4-Trifluoro-phenylacetic acid (1.0 mmol), Pd(OAc)2 (2 mol%), ligand (4 mol%), H2O2 (35% aqueous solution, 3.5 equiv.), base (1.5 equiv.) in solvent (3.0 mL) r.t., 24 h. Yields were determined by 1H NMR using CH3NO2 as the internal standard.

b

90°C.

c

2 mol% ligand.