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. Author manuscript; available in PMC: 2013 Mar 28.
Published in final edited form as: J Am Chem Soc. 2012 Mar 14;134(12):5524–5527. doi: 10.1021/ja301013h

Table 1.

Effect of Copper Source and Reagent Ratios on the Difluoromethylation of 1-butyl-4-iodobenzenea

graphic file with name nihms-362757-f0003.jpg
Entry CuX (eq) CsF (eq) TMSCF2H (eq) yield (%)
1 CuBr (1.0) 2.0 5.0 84
2 CuBr-SMe2 (1.0) 2.0 5.0 70
3 CuCI (1.0) 2.0 5.0 53
4 Cul (1.5) 1.5 1.5 26
5 Cul (3.0) 3.0 3.0 36
6 Cul (1.0) 1.0 5.0 55
7 Cul (1.0) 2.0 5.0 91
8 Cul (1.0) 3.0 3.0 75
9 Cul (1.0) 3.0 5.0 100
a

Reactions were performed with 0.1 mmol of 1-butyl-4-iodobenzene in 0.5 mL of NMP for 24 hours. The yield was determined by 19F NMR with 1-bromo-4-fluorobenzene as an internal standard added after the reaction.