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. Author manuscript; available in PMC: 2015 Jul 30.
Published in final edited form as: Chem Sci. 2014 Aug 4;5(11):4173–4178. doi: 10.1039/C4SC02155J

Table 1.

Evaluation of arene coupling partners and photocatalysts

graphic file with name nihms673574u1.jpg
Entry Leaving group (X) Amine (equiv.) Photocatalyst (mol%) Yielda (%)
1 CN 3 Ir(ppy)3 (1 mol%) 4%
2 I 3 Ir(ppy)3 (1 mol%) 5%
3 Br 3 Ir(ppy)3 (1 mol%) 50%
4 Cl 3 Ir(ppy)3 (1 mol%) 56%
5 F 3 Ir(ppy)3 (1 mol%) 16%
6 Cl 3 Ir(ppy)2(dtbbpy)PF6 (1 mol%) 75%
7 Cl 3 Ir(ppy)2(dtbbpy)PF6 (0.5 mol%) 78%
8 Cl 1.5 Ir(ppy)2(dtbbpy)PF6 (0.5 mol%) 77%
9b Cl 1.5 Ir(ppy)2(dtbbpy)PF6 (0.5 mol%) 84%
10c Cl 1.5 Ir(ppy)2(dtbbpy)PF6 (0.5 mol%) 87%
11 Cl 1.5 None 11%
12d Cl 1.5 Ir(ppy)2(dtbbpy)PF6 (0.5 mol%) 0%
13e Cl 1.5 Ir(ppy)2(dtbbpy)PF6 (0.5 mol%) 0%
a

Yield after 24 h determined by 1H NMR analysis of crude reaction mixture with internal standard. Reactions performed with 2 equiv. NaOAc and 0.25 M DMA.

b

With 3 equiv. H2O.

c

With 10 equiv. H2O, isolated yield.

d

Performed in the absence of light.

e

Performed in the absence of NaOAc.