(+)-2,2'-Methylenebis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole]

Oxidative Trifluoromethylation of Indoles

Typical Procedure: In a 4 mL TFE sealed glass vial, Pd(OAc)2 (4.4 mg, 0.02 mmol), PhI(OAc)2 (129 mg, 0.4 mmol), (+)-2,2'-methylenebis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole] (9.8 mg, 0.03 mmol), and TEMPO (15 mg, 0.1 mmol) are added. The glass vial is transferred to a glove box to add CsF (122 mg, 0.8 mmol), and the solution of the indole (0.2 mmol) in anhydrous CH3CN (2 mL) is added. Sequentially, TMSCF3 (0.8 mmol, 120 μL) is immediately added and the mixture is stirred for 6 hours at room temperature. After the reaction is completed, the solvent is removed under reduced pressure, and the residue is purified by fast chromatography in silica gel to give the desired compound.

• X. Mu, S. Chen, X. Zhen, G. Liu, Chem. Eur. J. 2011, 17, 6039.