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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 5. Selective Synthesis of 5.

graphic file with name nihms-123271-t0017.jpg
Entry Substrate(b) Crude Ratio 2:3:4:5 Product Isolated Yield 5
1 1a 0:0:0:100 graphic file with name nihms-123271-t0018.jpg 74 %
2 1a 0:0:0:100 graphic file with name nihms-123271-t0019.jpg 75 %
3 1b 0:15:0:85 graphic file with name nihms-123271-t0020.jpg 71 %
4 1d 0:10:0:90 graphic file with name nihms-123271-t0021.jpg 69 %
5 1c 5:10:10:75 graphic file with name nihms-123271-t0022.jpg 67 %(c)
6 1e 0:10:0:90 graphic file with name nihms-123271-t0023.jpg 85 %
7 1e 0:0:0:100 graphic file with name nihms-123271-t0024.jpg 76 %
(a)

Conditions: 1.0 equiv amine, 1.4 equiv Ar2Br, 1.2 equiv NaOt-Bu, 1 mol % Pd2(dba)3, 2 mol % P(t-Bu)2Me·HBF4, toluene (0.25 M), 110 °C.

(b)

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

(c)

This material contained 7 % of isomer 3 as an inseparable impurity.