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. Author manuscript; available in PMC: 2015 Mar 9.
Published in final edited form as: Synlett. 2014;26(3):335–339. doi: 10.1055/s-0034-1379015

Table 2.

Substrate Scopea

graphic file with name nihms-618846-t0005.jpg

entry substrate product yieldb
1 graphic file with name nihms-618846-t0006.jpg graphic file with name nihms-618846-t0007.jpg 71%
2 1b, R = SES 2b, R = SES 55%
3 1c, R = Ns 2c, R = Ns 51%
4 1d, R = Ms 2d, R = Ms 50%
5 graphic file with name nihms-618846-t0008.jpg graphic file with name nihms-618846-t0009.jpg 73%
6 graphic file with name nihms-618846-t0010.jpg graphic file with name nihms-618846-t0011.jpg 22%
7 graphic file with name nihms-618846-t0012.jpg graphic file with name nihms-618846-t0013.jpg 43%
8 graphic file with name nihms-618846-t0014.jpg graphic file with name nihms-618846-t0015.jpg 83%
8 1h, Ar = 4-F-Ph 2h, Ar = 4-F-Ph 81%
9 1i, Ar = 4-MeO-Ph 2i, Ar = 4-MeO-Ph 85%
10 graphic file with name nihms-618846-t0016.jpg graphic file with name nihms-618846-t0017.jpg 55%
a

Reaction conditions used: 1a (0.174 mmol, 1 equiv), Cu(eh)2 (0.026 mmol, 15 mol %), TEMPO (0.035 mmol, 20 mol %), toluene (1.74 mL) and O2 (1 atm, balloon).

b

Isolated yield after column chromatography

c

22% of the (Z)-isomer of 1f was recovered.

SES = 2-(trimethylsilyl)ethanesulfonyl, Ns = 4-nitrophenylsulfonyl, Ms = methane sulfonyl.