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. Author manuscript; available in PMC: 2009 Sep 1.
Published in final edited form as: J Am Chem Soc. 2005 Jun 22;127(24):8644–8651. doi: 10.1021/ja0430346

Table 4. Selective Synthesis of 3.

graphic file with name nihms-123271-t0009.jpg
Entry Substrate(c) Crude Ratio 2:3:4:5 Product Isolated Yield 3
1 1a 25:65:10:0 graphic file with name nihms-123271-t0010.jpg 44 %(d)
2 1a 48:48:2:2 -
3 1b 20:70:10:0 graphic file with name nihms-123271-t0011.jpg 65 %(d)
4 1b 30:65:2:3 -
5 1c 10:80:10:0 graphic file with name nihms-123271-t0012.jpg 69 %(e)
6 1c 0:100:0:0 graphic file with name nihms-123271-t0013.jpg 64 %
7 1d 0:100:0:0 graphic file with name nihms-123271-t0014.jpg 75 %
8 1d 0:90:10:0 graphic file with name nihms-123271-t0015.jpg 58 %
9 1d 30:60:10:0 graphic file with name nihms-123271-t0016.jpg 49 %
(a)

Conditions: 1.0 equiv amine, 1.4 equiv Ar2Br, 1.2 equiv NaOt-Bu, 1 mol % Pd2(dba)3, 2 mol % 11, toluene (0.25 M), 110 °C.

(b)

11 = 2-diphenylphosphino-2′-(N,N-dimethylamino)biphenyl.

(c)

1a: Ar = p-(MeO)C6H4; 1b: Ar = p-(Cl)C6H4; 1c : Ar = p-(NC)C6H4; 1d: Ar = p-(t-BuO2C)C6H4.

(d)

Ligand = dppp.

(e)

This material contained 7 % of 4c as an inseparable impurity.