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. Author manuscript; available in PMC: 2014 Jul 17.
Published in final edited form as: J Am Chem Soc. 2013 Jul 9;135(28):10326–10329. doi: 10.1021/ja4055492

Table 2. Ortho-Iodination of Phenylacetic Amidesa ,b, c, d, e.

graphic file with name nihms-504176-t0006.jpg
a

Ar = (4-CF3)C6F4.

b

Reaction conditions for mono-iodination: 0.30 mmol of phenylacetic amide, 2 mol % Pd(OAc)2, 0.75 mmol I2, 0.36 mmol CsOAc, 0.30 mmol NaHCO3, 150 mg 4 Å molecular sieves and 5.0 mL of t-AmylOH/DMF (1:1) in a sealed tube, 65 °C, 20 h.

c

For products 2g, 2h and 2r, 5 mol % Pd(OAc)2 was used.

d

Reaction conditions for di-iodination: 0.10 mmol of phenylacetic amide, 5 mol % Pd(OAc)2, 0.50 mmol I2, 0.24 mmol CsOAc, 0.20 mmol NaHCO3, 50 mg 4 ° molecular sieves and 2.0 mL of t-AmylOH/DMF (1:1) in a sealed tube, 65 °C, 20 h.

e

Yields of the isolated product.

f

Ratio was determined by the 1H NMR spectroscopy.