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. Author manuscript; available in PMC: 2013 Jun 6.
Published in final edited form as: J Am Chem Soc. 2012 May 24;134(22):9062–9065. doi: 10.1021/ja302537j

Table 2.

Scope of AgNTf2-Catalyzed Cycloaddition Reactionsa

graphic file with name nihms380577t3.jpg
Entry Catalyst
mol%
Time
(h)
Product Yieldb
(%)
Entry Catalyst
mol%
Time
(h)
Product Yieldb
(%)
1 1.0 2 graphic file with name nihms380577t4.jpg 82 9 1.0 1 graphic file with name nihms380577t5.jpg 81
2 2.0 1.5 graphic file with name nihms380577t6.jpg 72 10d 2.0 3 graphic file with name nihms380577t7.jpg 75
3 1.0 7 graphic file with name nihms380577t8.jpg 78 11e 2.0 3 graphic file with name nihms380577t9.jpg 83
4 2.0 3 graphic file with name nihms380577t10.jpg 84 12d 10 22 graphic file with name nihms380577t11.jpg 67
13d,f 10 7 80
5c 2.0 4 graphic file with name nihms380577t12.jpg 67 14 1.0 1 graphic file with name nihms380577t13.jpg 95
15 0.5 3 92
6c 2.0 4 graphic file with name nihms380577t14.jpg 74 16 1.0 3 graphic file with name nihms380577t15.jpg 84
7d 2.0 3 graphic file with name nihms380577t16.jpg 73 17 1.0 2 graphic file with name nihms380577t17.jpg 85
8e 2.0 1 graphic file with name nihms380577t18.jpg 70 18 1.0 6 graphic file with name nihms380577t19.jpg 94
a

Reactions were carried out using 0.5 or 1.0 mmol of diazine and 1.3 equiv of the siloxy alkyne with 8AgNTf2 ratio of 1.1:1.

b

Isolated yields.

c

For the determination of the regiochemistry of the product, see the Supporting Information.

d

2.0 equiv of siloxy alkyne was used.

e

1.5 equiv of siloxy alkyne was used.

f

The reaction was carried out in refluxing CH2Cl2.