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. Author manuscript; available in PMC: 2012 Jun 3.
Published in final edited form as: Org Lett. 2011 May 10;13(11):2936–2939. doi: 10.1021/ol2009939

Table 2.

Fe(OAc)2/L12-catalyzed cycloaddition of cyanoalkynes and symmetrical alkynesa

entry cyanoalkyne (1) alkyne (2) time(h) product (% yield)b
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1 R = Me, 1a 2a 2h 3a, 70
2 R = Et, 1b 2a 26h 3b, 86
3 R = Ph, 1c 2a 5h 3c, 75
4 R = H, 1d 2a 26h 3d, 30
5 R = SiMe3, 1e 2a 6h 3e, 57
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6 1a 2b 6h 3f, 71
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7 1a 2c 5h 3g, 54c
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8 R = Et, 1f 2a 4h 3h, 41
9 R = Ph, 1g 2a 4h, 3i, 45
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10 1h 2a 4h 3j, 41
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11 1i 2a 4h 3k, 65
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12 1j 2b 4h 3l, 64
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13 1k 2a 24h 3m, 40d
a

Reaction Conditions: 0.4 M 1, 0.4 M 2, 10 mol % Fe(OAc)2, 13 mol % L12, 20 mol % Zn, DMF, 85 °C.

b

Average of at least two reaction runs.

c

2 equiv of alkyne.

d

Reaction Conditions: 0.4 M 1, 0.4 M 2, 20 mol % Fe(OAc)2, 26 mol % L12, 40 mol % Zn, DMF, 85 °C.