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. Author manuscript; available in PMC: 2013 Jun 6.
Published in final edited form as: J Am Chem Soc. 2012 May 24;134(22):9034–9037. doi: 10.1021/ja301553c

Scheme 3.

Scheme 3

Substrate Scope for Cu/Ru-Catalyzed Trifluoromethylation of Boronic Acids[a]

[a] General conditions: substrate (1 equiv), CF3I (5 equiv), [Cu] (0.2 equiv), Ru(bpy)3Cl2•6H2O (0.01 equiv), K2CO3 (1 equiv), DMF (0.17 M in substrate), 60 °C, 12 h, 26 W compact fluorescent light bulb; Isolated yield (≥95% purity). [b] 19F NMR yield. [c] 0.5 equiv of CuOAc. [d] Isolated as a 1:1 mixture with inseparable protodeboronated product. [e] 0.1 equiv of CuOAc. [f] Isolated as a 10:1 mixture with inseparable protodeboronated product. [g] 3 equiv of CF3I. [h] Reaction run at 70 °C. [i] Reaction run at 40 °C. [j] 0.05 equiv of CuOAc.