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. Author manuscript; available in PMC: 2010 Feb 16.
Published in final edited form as: J Am Chem Soc. 2008 Apr 30;130(20):6586. doi: 10.1021/ja077074w

Table 4.

Comparison of the Activity of CyPF-t-Bu, XPhos, and SiPr for the Reactions of 4-Chlorotoluene with a Primary Alkylamine.a

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Entry Ligand Loading Solvent T[°C]b t [ h] Conversionc
(%)		 A:B
1 Pd(OAc)2/1 0.01 DME 100 48 100(95) 100:0
2 Pd(OAc)2/2 0.05 Toluene 100 48 13 18:1
3 Pd(dba)2/2 0.1 Toluene 100 48 25 10:1
4 Pd(OAc)2/2 0.1 Toluene 100 48 16 39:1
5 Pd(OAc)2/2 0.5 Toluene 100 12 96(91) 2.7:1
6 Pd(dba)2/2 0.5 Toluene 100 12 100(93) 2.3:1
7 3 0.005 Toluene 110 48 40 >50:1
8 3 0.05 Toluene 110 48 76 15.3:1
9 3 0.5 Toluene 110 12 100 4.3:1
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a

The experiments were conducted with a 1:1 ratio of Pd/CyFP-t-Bu or 1:2 ratio of Pd/XPhos, 1 mmol of 4-chlorotoluene and 1.2 equiv 1-octylamine, and 1.4 equiv base in 1.0 mL solvent.

b

Bath temperature.

c

Determined by 1H NMR analysis of the crude product. Isolated yields are indicated in parentheses.