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. Author manuscript; available in PMC: 2012 Jan 12.
Published in final edited form as: Tetrahedron Lett. 2011 Jan 12;52(2):177–180. doi: 10.1016/j.tetlet.2010.10.109

Table 1.

Mercury-catalyzed IFCA reaction of 5a

graphic file with name nihms-257222-t0007.jpg

Entry HgX2, (equiv) Conditions Yield %,a (trans:cis)b
1 Hg(OTf)2, (0.005) PhMe, rt, 1.5 h; 48 °C, 25 h 40%,d 12.5:1
2 Hg(OTf)2, (0.005) PhMe, rt, 20 min; 60 °C, 25 h 54%,d 8:1,
3 Hg(OTf)2, (0.005) PhMe, 45 °C, 4 h 54%, 9:1
4 Hg(OTf)2, (0.005) PhMe, 55 °C, 4 h 50%, 9:1
5 Hg(OTf)2, (0.005) PhMe, 110 °C, 10 min 34%, <9:1
6 Hg(OTf)2,(0.01)c PhMe, 60 °C, 30 min; 110 °C, 12 hc 0
7 Hg(OTf)2, (0.005) MeCN, rt, 20 min; 70-80 °C, 19 h 0
8 Hg(OTf)2, (0.005) CH2Cl2, rt, 35 min; 90 °C, 5 h 13%,d 12.5:1
9 Hg(OTf)2, (0.005) ClCH2CH2Cl, rt, 35 min; 90 °C, 5 h 27%,d 15:1
10 Hg(SO3C4F9)2, (0.005) PhMe, rt, 24 h; 80 °C, 15 min e
a

Yields are for isolated products unless otherwise stated.

b

The diastereomeric ratio was determined by analysis of the 1H NMR spectrum of the crude reaction mixture.

c

2,6-di-tert-butylpyridine was added.

d

Crude yield.

e

A complex mixture was formed.