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. Author manuscript; available in PMC: 2010 Dec 1.
Published in final edited form as: J Am Chem Soc. 2008 Mar 6;130(12):3736–3737. doi: 10.1021/ja710990d

Table 1.

Au(I)-Catalyzed Arene Synthesis: Enyne Scope

graphic file with name nihms-253765-t0005.jpg
entry enyne cp yielda conditions Ab yieldc conditions Bb yieldc
1 graphic file with name nihms-253765-t0006.jpg 7 94% graphic file with name nihms-253765-t0007.jpg 8 81% graphic file with name nihms-253765-t0008.jpg 9 79%

2 graphic file with name nihms-253765-t0009.jpg 11 83% graphic file with name nihms-253765-t0010.jpg 12 72% graphic file with name nihms-253765-t0011.jpg 13 66%

3 graphic file with name nihms-253765-t0012.jpg 15 82% graphic file with name nihms-253765-t0013.jpg 16 31% (+ 54% 17) graphic file with name nihms-253765-t0014.jpg 17 80% (15:1)d
4 19 72% 20 93% 21 25% (1:1)d (+ 62% 20)
5 23 75% 24 60% 25 85% (1.6:1)d

6 graphic file with name nihms-253765-t0015.jpg 27 41% graphic file with name nihms-253765-t0016.jpg 28 58% graphic file with name nihms-253765-t0017.jpg 29 76%
7 31 62% 32 86% 33 93%
8 35 79% 36 83% 37 63%
9 39 79% 40 95% 41 59%
10 43 87% 44 71% 45 60%
11 47 73% 48 89% 49 71%
12 51 74% 52 64% 53 90%

13 graphic file with name nihms-253765-t0018.jpg 55 77% graphic file with name nihms-253765-t0019.jpg 56 69% graphic file with name nihms-253765-t0020.jpg 57 79%

14 graphic file with name nihms-253765-t0021.jpg 59 50% graphic file with name nihms-253765-t0022.jpg 60 65% N/Ae
15 62 62% 63 53%
16 65 58% 66 66%
a

Isolated yields of cis-cyclopropane Reactions run with 3:1 ratio of 1:enyne.

b

A: 5% AgOTf, 5% (ArO)3PAuCl, CH2Cl2. B: 5% AgSbF6, 5% (ArO)3PAuCl, CH2Cl2.

c

Isolated yields

d

Ratio of regioisomers.

e

Conditions B were not investigated with 58, 61 and 64.