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. Author manuscript; available in PMC: 2013 Jan 29.
Published in final edited form as: Angew Chem Int Ed Engl. 2011 Sep 20;50(45):10694–10698. doi: 10.1002/anie.201104475

Table 2.

Nickel-Catalyzed Cycloaddition of Diynes and Nitriles.a,b

Entry Diyne Nitrile Product Yieldc
graphic file with name nihms416666t1.jpg
X = C(CO2Et)2 		graphic file with name nihms416666t2.jpg graphic file with name nihms416666t3.jpg
1 1 a (Ar = Ph) 1a 98%
2 1 b (Ar = 2-Me-Ph) 1b 87%
3 1 c (Ar = 4-OMe-Ph) 1c 90%
4 1 d (Ar = 4-CF3-Ph) 1d 99%
5 1 e (Ar = 3,5-F2-Ph) 1e >99%
6 1 f (Ar = 2-Naphthyl) 1f 96%
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X = C(CO2Me)2 		graphic file with name nihms416666t5.jpg graphic file with name nihms416666t6.jpg
7 2 a (Ar = Ph) 2a 92% (86%)d
8 2 b (Ar = 2-Me-Ph) 2b 85% (81%)d
9 2 c (Ar = 4-OMe-Ph) 2c 89% (64%)d
10 2 d (Ar = 4-CF3-Ph) 2d 98% (94%)d
11 2 e (Ar = 3,5-F2-Ph) 2e >99%
graphic file with name nihms416666t7.jpg graphic file with name nihms416666t8.jpg
12 2 g 2g >99%e
graphic file with name nihms416666t9.jpg graphic file with name nihms416666t10.jpg
13 2 h (R = Me) 2h 94% (69%)d
14 2 i (R = i-Pr) 2i 90% (72%)d
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15 3 a 3a 73% (78%)d
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16 4 a 4a 80% (93%)d
graphic file with name nihms416666t13.jpg graphic file with name nihms416666t14.jpg
17 5 a 5a 93%
a

Reaction Conditions: 3 mol % Ni(COD)2, 3 mol % Xantphos, diyne (1 equiv., 0.1 M), nitrile (1.5 equiv.), toluene, RT, 3 h.

b

Nitriles were neither distilled nor degassed. Nitriles were used as received.

c

Isolated yields.

d

Yields from reference 6a.

e

The reaction was run at 100 °C.