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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

Table 1.

Optimization of Reaction Between 1 and CF3I[a]

graphic file with name nihms380571t1.jpg
Entry [Cu] Base Yield
1 Cu(OTf)2 K2CO3 14%
2 [Cu(OTf)]2•C6H6 K2CO3 28%
3 Cul K2CO3 34%
4 Cu K2CO3 40%
5 Cu(OAc)2 K2CO3 68%
6 CuOAC K2CO3 76%
7 CuOAC NaOAc 34%
8 CuOAC KF 50%
9 CuOAC none 6%
10[b] CuOAC K2CO3 1%
11[c] none K2CO3 3%
12[d] CuOAC K2CO3 3%
[a]

General conditions: substrate (0.05 mmol, 1 equiv), CF3I (5 equiv), [Cu] (0.2 equiv), Ru(bpy)3Cl2•6H2O (0.01 equiv), base (1 equiv), DMF (0.17 M in substrate), 60 °C, 12 h, 26 W compact fluorescent light bulb. 19F NMR yield.

[b]

General conditions, but with no light.

[c]

General conditions, but with no CuOAc.

[d]

General conditions, but with no Ru(bpy)3Cl2•6H2O.