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. Author manuscript; available in PMC: 2012 Nov 23.
Published in final edited form as: J Am Chem Soc. 2011 Nov 2;133(46):18566–18569. doi: 10.1021/ja208068w

Table 3.

Scope of Directing Groups for Pd/Ru-Catalyzed C–H Arylation

graphic file with name nihms-336332-t0023.jpg

Entry Substrate Product Isolated Yielda
1 graphic file with name nihms-336332-t0024.jpg graphic file with name nihms-336332-t0025.jpg 72%
2 b graphic file with name nihms-336332-t0026.jpg graphic file with name nihms-336332-t0027.jpg 79%
3c,d graphic file with name nihms-336332-t0028.jpg graphic file with name nihms-336332-t0029.jpg 53%
4 d graphic file with name nihms-336332-t0030.jpg graphic file with name nihms-336332-t0031.jpg 44%
5 e graphic file with name nihms-336332-t0032.jpg graphic file with name nihms-336332-t0033.jpg 49%
6f,g,h graphic file with name nihms-336332-t0034.jpg graphic file with name nihms-336332-t0035.jpg 50%
[a]

General procedure: Substrate (1.0 equiv), Pd(OAc)2 (0.1 equiv), Ru(bpy)3Cl2•6H2O (0.025 equiv), PhN2BF4 (4.0 equiv), MeOH (0.1 M in substrate), rt, 4 h, 26 W compact fluorescent light bulb.

[b]

General conditions but with 0.05 equiv of Ru(bpy)3Cl2•6H2O.

[c]

Ag2CO3 (1.0 equiv) used as an additive.

[d]

Reaction run for 5 h.

[e]

3.5 equiv of PhN2BF4

[f]

General conditions but with 0.20 equiv of Pd(OAc)2.

[g]

Reaction run for 5.5 h.

[h]

MeOH (0.2 M in substrate).