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. Author manuscript; available in PMC: 2014 Nov 15.
Published in final edited form as: Org Lett. 2013 Nov 1;15(22):10.1021/ol402904d. doi: 10.1021/ol402904d

Table 2.

Reaction Scope with Respect to Phenolsa

graphic file with name nihms537547t2.jpg

entry phenol product yield,
%
1 4-tBu-phenol graphic file with name nihms537547t3.jpg 88
73b
2 4-SMe-phenol graphic file with name nihms537547t4.jpg 75
3 3-CF3-phenol graphic file with name nihms537547t5.jpg 55
4 4-Br-phenol graphic file with name nihms537547t6.jpg 78
5 3-I-phenol graphic file with name nihms537547t7.jpg 56
6 3-CO2Me-phenol graphic file with name nihms537547t8.jpg 84
7 3-Cl-4-Me-phenol graphic file with name nihms537547t9.jpg 77
8 2-Cl-4-MeO-phenol graphic file with name nihms537547t10.jpg 78
9c 3-amino-phenol graphic file with name nihms537547t11.jpg 57
a

Scale: 0.5 mmol; time: 2–8 h; 1/1 amide/phenol ratio, 110 °C, 11% catalyst = 22 mol % Cu. Please see Supporting Information for details.

b

Scale: 3.2 mmol, 5.5 mol % (CuOH)2CO3.

c

Amide/phenol ratio: 1/2.