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. Author manuscript; available in PMC: 2012 Jun 17.
Published in final edited form as: Org Lett. 2011 May 23;13(12):3218–3221. doi: 10.1021/ol201123b

Table 1.

Optimization of Reaction Conditions.a

graphic file with name nihms298989u2.jpg
entry ligand product ratio 8g:6a:12b
1 graphic file with name nihms298989t1.jpg R = Me (13) 14:0:1
2 R = iPr 4:0:1
3 graphic file with name nihms298989t2.jpg R = NMe2 3:0:1
4 R = Me 4:0:1
5 graphic file with name nihms298989t3.jpg (14) 10:0:1
6 graphic file with name nihms298989t4.jpg R = Ph (4)c 0:1:0
7 R = Cy (15)c >20:0:1 (63% yield)d
8 PCy3•HBF4 >20:0:1
a

Conditions: 1.0 equiv 5b, 1.2 equiv PhCl, 2.4 equiv NaOtBu, 1 mol % Pd2(dba)3, 4 mol % ligand, toluene (0.25 M), 100 °C, 5–24 h.

b

Product ratios were determined by 1H NMR analysis of crude reaction mixtures.

c

The reaction was conducted using 2 mol % ligand.

d

The product was isolated with 25:1 dr, although analysis of the crude reaction mixture indicated the product had been formed with 8:1 dr.