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. Author manuscript; available in PMC: 2011 Aug 1.
Published in final edited form as: Org Lett. 2007 Feb 2;9(5):875–878. doi: 10.1021/ol063111x

Table 3.

Scope and Selectivity in Nickel-Catalyzed Coupling of α-Olefins and Isocyanates.a

graphic file with name nihms308278u4.jpg
entry R1 R2 R3 product(s) yield a; b; c (%)b
1 n-hexyl Cy - 1a, 1b 79; 14; 0
2 n-hexyl t-Bu - 2a, 2b 74; 17; 0
3c graphic file with name nihms308278t1.jpg Cy - 3a 72; 0; 0
4 graphic file with name nihms308278t2.jpg t-Bu - 4a 91; 0; 0
5c graphic file with name nihms308278t3.jpg Cy - 5a, 5b 74; 5; 0
6 graphic file with name nihms308278t4.jpg t-Bu - 6a, 6b 71; 10; 0
7c PhCH2 Cy Ph 7a, 7b, 7c 65; 8; 22
8c PhCH2 t-Bu Ph 8a, 8b, 8c 83; 1d; 5d
9c graphic file with name nihms308278t5.jpg Cy - 9a 86; 0; 0
10 graphic file with name nihms308278t6.jpg t-Bu - 10a 82; 0; 0
11 graphic file with name nihms308278t7.jpg Cy - 11a, 11b 74; 13; 0
12 graphic file with name nihms308278t8.jpg t-Bu - 12a, 12b 72; 12; 0
13 graphic file with name nihms308278t9.jpg Cy - 13a 24; 0; 0
14 graphic file with name nihms308278t10.jpg t-Bu - 14a, 14b 70; 2; 0
15 graphic file with name nihms308278t11.jpg Cy - 15a, 15b 68; 17; 0
16 graphic file with name nihms308278t12.jpg t-Bu - 16a, 16b 65; 9; 0
a

Standard conditions (see Supporting Information): Reactions were run with 0.5 mmol 1-octene, 1.0 mmol tert-butyl isocyanate, 0.05 mmol

Ni(cod)2, and 0.05 mmol IPr in 0.5 mL toluene under Ar(g) in a sealed

tube at 60 °C for 18–24 h.

b

Isolated yields.

c

Reaction was run using 2 mL toluene.

d

Isolated as a mixture of 8b and 8c, with relative ratios determined by 1H NMR.