Skip to main content
. Author manuscript; available in PMC: 2015 Nov 24.
Published in final edited form as: Adv Synth Catal. 2014 Oct 1;356(17):3659–3667. doi: 10.1002/adsc.201400695

Table 1.

Optimization of the direct arylation of 2-phenyl-1,3-dithiane.

graphic file with name nihms-691982-f0004.jpg
Entry Rase [PdCl(C3H5)]2 mol % NiXantphos mol % Temp./Time °C/ h Yield (%)[a] 3a
1 LiN(SiMe3)2 10 20 24 /2 71
2 NaN(SiMe3)2 10 20 24 /2 83
3 KN(SiMe3)2 10 20 24 /2 83
4 NaOt-Ru 10 20 24 /2 -
5 NaN(SiMe3)2 5 10 24 /2 89
6 NaN(SiMe3)2 5 10 24 /1 79
7 NaN(SiMe3)2 2.5 5 24 /2 92
8[b] NaN(SiMe3)2 2.5 5 24 /2 93
9 NaN(SiMe3)2 2.5 5 60 /0.5 95
10 NaN(SiMe3)2 1.25 2.5 24 /2 35
11 NaN(SiMe3)2 1.25 2.5 24 /3 37
[a]

Yield determined by 1H NMR integration of the crude reaction mixture using 0.1 mmol CH2Br2 as the internal standard.

[b]

Reaction concentration is 0.07 M (entry 8). Reaction concentration for other entries is 0.10 M.