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. Author manuscript; available in PMC: 2015 Aug 11.
Published in final edited form as: Adv Synth Catal. 2014 Jul 30;356(11-12):2517–2524. doi: 10.1002/adsc.201400679

Table 3.

Optimization of palladium-catalyzed DCCP of benzyl phenyl sulfide.

graphic file with name nihms640057u3.jpg
entry 1a:2a:3a solvent T (°C) time (h) Pd: NiXantPhos (mol %) 4aa (%)
1 2:1:2 THF 80 12 10:20 45
2 2:1:3 THF 80 12 10:20 0
3 1:2:2 THF 80 12 10:20 52
4 1:2:2 THF 50 12 10:20 53
5 1:2:2 THF R.T. 12 10:20 60
6 1:2:2 THF R.T. 6 10:20 67
7 1:2:2 THF R.T. 1 10:20 80
8 1:2:2 THF R.T. 0.5 10:20 86
9 1:2:2 THF R.T. 0.25 10:20 76
10 1:2:2 THF R.T. 0.5 5:10 67
11 1:2:2 THF R.T. 0.5 5:10 64b
12 1:2:2 CPME R.T. 0.5 10:20 0
13 1:2:2 DME R.T. 0.5 10:20 58
14 1:2:2 dioxane R.T. 0.5 10:20 0
15 1:2:2 hexanes R.T. 0.5 10:20 0
16 1:2:2 toluene R.T. 0.5 10:20 0
a

Yields determined by 1H NMR analysis of crude mixture with CH2Br2 as internal standard.

b

concentration 0.2 M.