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. Author manuscript; available in PMC: 2015 Jan 8.
Published in final edited form as: J Am Chem Soc. 2013 Dec 16;136(1):48–51. doi: 10.1021/ja410704d

Table 2.

Nickel/iodide co-catalyzed epoxide ring opening with aryl halidesa

graphic file with name nihms550409t2.jpg
entry deviation from above yield (%)b 2:3
1 none 81 > 95:5
2 No TEA•HCl 32 89:11
3 15 mol % NaI 67 > 95:5
4 25 mol % Bu4NI in place of NaI 79 95:5
5 12.5 mol % ZnI2 in place of NaI 46 88:12
6 12.5 mol % MnI2 in place of NaI 61 95:5
7 No NaI, 12 hours 68 > 95:5
8 No NaI, 24 hours 75 > 95:5
9 25 mol % NaBr in place of NaI 52 > 95:5
12 NiI2 in place of NiI2·xH2O 86 > 95:5
13 2 equiv. of Mn in place of Zn 59 95:5
14c 2 equiv. of TDAE in place of Zn 48d >95:5
15 Heated to 60 °C for 12 h 50 93:7
16 I-Ph in place of Br-Ph 51 91:9
a

Reactions were run with 1 equiv of Et3N•HCl and 2 equiv of zinc dust; 0.1 equiv nickel catalyst, ligand; 0.2 equiv pyridine, 0.25 equiv sodium iodide, and 1.34 equiv of 1a in 3 mL DMPU.

b

Uncorrected GC yield of 2aa.

c

TDAE = tetrakis(dimethylamino)ethylene.

d

Bromobenzene (52%) remained, but no biaryl or benzene was formed.