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. Author manuscript; available in PMC: 2016 Jan 31.
Published in final edited form as: Chem Sci. 2014 Nov 10;6(2):1115–1119. doi: 10.1039/c4sc03106g

Table 1.

Cross-electrophile coupling of Bn-OH with Ar-X.a

graphic file with name nihms-642746-f0004.jpg
Entry X Catalystb Yield 3 (A%)c 3:4
1 Br [Ni] only 3 1:1
2 Br Co(Pc) only 0 ND:3
3 Br [Ni], Co(Pc) 73 1:ND
4 Br [Ni], CoCl2 4 4:1
5 Br [Ni], NaI (25 mol%) 25 1:1
6 Br [Ni], Co(Pc), Mn instead of Zn 64 4:1
7 Br NiBr2•3H2O, Co(Pc) 1 1:6
8 Br No [Ni] and no Co(Pc) 0 0:1
9d,e I [Ni] only 71 7:1
10e I Co(Pc) only 0 ND:1
11d,e I [Ni], Co(Pc) 83 17:1
12 I [Ni], Co(Pc) 83 83:1
13 I [Ni], NaI (25 mol%) 64 8:1
14 I [Ni], Co(Pc), Mn instead of Zn 42 1.4:1
a

Reactions run at 0.25 M in DMA. BnOMs was formed in situ from BnOH, Ms2O (1.44 equiv), and EtN(i-Pr)2 (1.6 equiv). See Supporting Information.

b

[Ni] = 7 mol% NiBr2•3H2O and 5 mol% dtbbpy.19 Co(Pc) = 1 mol% cobalt phthalocyanine.

c

Yields and ratios reported as GC Area%.

d

Reaction run at 60 °C.

e

Reaction complete within 1 h.