Skip to main content
. Author manuscript; available in PMC: 2010 Feb 20.
Published in final edited form as: J Org Chem. 2009 Feb 20;74(4):1663. doi: 10.1021/jo802594d

Table 4.

Coupling of bromo- and iodoarenes with aliphatic thiols catalyzed by Pd(OAc)2 and CyPF-tBu.a

graphic file with name nihms-91345-f0009.jpg
Entry Ar X R Cat. [mol %] T [°C] t [h] Yield [%]
1 4-Tol Br octyl 0.05 90 2 96
2b Br octyl 0.05 90 2 98
3 I octyl 0.05 70 2 96
4 Ph Br octyl 0.05 90 4 98
5 I octyl 0.05 70 4 98
6 4-anisyl Br octyl 0.05 90 3 98
7 I octyl 0.05 70 3 96
8 Ph Br 2-methylbutyl 0.05 90 5 90
9 I 2-methylbutyl 0.05 70 6 96
10 3-anisyl Br 2-methylbutyl 0.05 90 6 96
11 I 2-methylbutyl 0.05 70 6 96
12 Ph Br sec-butyl 0.05 90 4 90
13 I sec-butyl 0.05 70 4 93
14 4-Tol Br cyclohexyl 0.05 90 6 94
15 I cyclohexyl 0.05 70 6 99
16 Br tert-butyl 0.05 90 5 93
17 4-trifluoromethylphenyl Br tert-butyl 0.05 90 3 79
18 1-naphthyl Br octyl 0.05 90 8 96
19 I octyl 0.05 90 12 93
20 2-anisyl Br octyl 0.05 110 4 99
21 I octyl 0.05 90 12 96
22 2-Tol Br octyl 0.01 110 12 99
23 I octyl 0.05 70 12 98
24 2,5-dimethylphenyl I tert-butyl 0.05 90 12 93
25 2,6-dimethylphenyl Br tert-butyl 0.25 110 4 92
26 I tert-butyl 0.1 110 8 94
a

All experiments were conducted with a 1:1 ratio of metal to ligand, 1 mmol of both ArX and thiol, and 1.1 equiv of NaOtBu in DME (1.5 mL) at the appropriate temperature.

b

Reaction performed without using a drybox.