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. Author manuscript; available in PMC: 2009 Jan 15.
Published in final edited form as: J Org Chem. 2006 Apr 14;71(8):3198–3209. doi: 10.1021/jo0602221

Table 5.

Facile O-Arylation of Carboxylic Acidsa

entry carboxylic acid silylaryl
triflate
(equiv)
CsF
(equiv)
time
(h)
product %
isolated
yield
1 graphic file with name nihms-60962-t0160.jpg 1a (2.0) 4.0 24 graphic file with name nihms-60962-t0161.jpg 81
2 graphic file with name nihms-60962-t0162.jpg 1a (2.0) 4.0 24 graphic file with name nihms-60962-t0163.jpg 66
4 graphic file with name nihms-60962-t0164.jpg 1a (2.0) 4.0 24 graphic file with name nihms-60962-t0165.jpg 96
5 graphic file with name nihms-60962-t0166.jpg 1b (2.0) 4.0 24 graphic file with name nihms-60962-t0167.jpg 98
6 graphic file with name nihms-60962-t0168.jpg 1a (2.0) 4.0 24 graphic file with name nihms-60962-t0169.jpg 84
7 graphic file with name nihms-60962-t0170.jpg 1c (2.0) 4.0 24 graphic file with name nihms-60962-t0171.jpg 81
8 graphic file with name nihms-60962-t0172.jpg 1a (2.0) 4.0 24 graphic file with name nihms-60962-t0173.jpg 75
9 graphic file with name nihms-60962-t0174.jpg 1a (2.0) 4.0 24 graphic file with name nihms-60962-t0175.jpg 89
10 graphic file with name nihms-60962-t0176.jpg 1b (2.0) 4.0 24 graphic file with name nihms-60962-t0177.jpg 89
11 graphic file with name nihms-60962-t0178.jpg 1a (2.0) 4.0 24 graphic file with name nihms-60962-t0179.jpg 45
12 graphic file with name nihms-60962-t0180.jpg 1a (2.0) 4.0 24 graphic file with name nihms-60962-t0181.jpg 33
a

All reactions were run under the following reaction conditions, unless otherwise specified: 0.25 mmol of the carboxylic acid and the indicated amount of silylaryl triflate and CsF were stirred in 4 mL of MeCN at room temperature.