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. Author manuscript; available in PMC: 2011 Jul 16.
Published in final edited form as: Org Lett. 2010 Jul 16;12(14):3117–3119. doi: 10.1021/ol101017z

Table 1.

Reaction of Carboxylic Acids with Arynesa

entry acid product % yieldb
1 graphic file with name nihms-214059-t0003.jpg graphic file with name nihms-214059-t0004.jpg 77
2c 1 graphic file with name nihms-214059-t0005.jpg 50
3 graphic file with name nihms-214059-t0006.jpg graphic file with name nihms-214059-t0007.jpg 72
4 graphic file with name nihms-214059-t0008.jpg graphic file with name nihms-214059-t0009.jpg 68
5 graphic file with name nihms-214059-t0010.jpg graphic file with name nihms-214059-t0011.jpg 58
6 graphic file with name nihms-214059-t0012.jpg graphic file with name nihms-214059-t0013.jpg 62
7 graphic file with name nihms-214059-t0014.jpg graphic file with name nihms-214059-t0015.jpg 44
8 graphic file with name nihms-214059-t0016.jpg graphic file with name nihms-214059-t0017.jpg 80
9d 17 graphic file with name nihms-214059-t0018.jpg 71
10 graphic file with name nihms-214059-t0019.jpg graphic file with name nihms-214059-t0020.jpg 22
a

Reaction conditions: 0.25 mmol of acid, 1.5 equiv of benzyne precursor and 4.0 equiv of CsF in 15 mL of THF were heated in a closed vial at 125 °C for 24 h.

b

Isolated yield.

c

3.0 Equiv of benzyne precursor, 6.0 equiv of CsF and 5 mL of DME were used.

d

3-Methoxy-2-(trimethylsilyl)phenyl triflate was used as the aryne precursor.