Fig. 2: Screening and synthesis of N-CF3 amidyl radical precursors.
From: Direct synthesis of N-trifluoromethyl amides via photocatalytic trifluoromethylamidation
A Synthesis of N-CF3 O-N imidates 1 from acetonitrile for radical trifluoromethylamidation of arene 2a. B Possible pathways for the formation of by-product 4a. C Preparation of N-CF3 imidoxyl pyridinium salts from diverse nitriles. aReaction conditions: 1 (0.1 mmol), 2a (0.3 mmol), Ir(dFppy)3 (0.001 mmol), DCM (3 mL), Blue LEDs, under N2, rt, 12 h, 19F NMR yields using PhCF3 as an internal standard. bReaction conditions: step1: PhICF3Cl (1.5 mmol), RCN (3.5 mL), 80 °C, 2 h; step 2: pyridine-N-oxide (1.0 mmol), NaX (2.0 mmol), isolated yields. cReaction conditions: N-CF3 imidoyl chlorides (1.1 mmol), pyridine-N-oxide (1.0 mmol), NaX (2.0 mmol), MeCN (4 mL), RT, 12 h. BHT Butylated hydroxytoluene, TEMPO 2,2,6,6-Tetramethylpiperidinyloxy.
