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. Author manuscript; available in PMC: 2016 Sep 9.
Published in final edited form as: J Am Chem Soc. 2015 Aug 27;137(35):11246–11249. doi: 10.1021/jacs.5b07203

Table 1.

Influence of Nucleophile and Ligand on Reactivitya

graphic file with name nihms797607u2.jpg
entry amine ligand T (°C) conv (%)a,b yield (%)a
1 graphic file with name nihms797607t1.jpg RuPhos 95 0 –
2 graphic file with name nihms797607t2.jpg CPhos 95 0 –
3 graphic file with name nihms797607t3.jpg RuPhos 95 0 –
4 graphic file with name nihms797607t4.jpg RuPhos 95 80 45
5 graphic file with name nihms797607t5.jpg CPhos 95 85 62
6 graphic file with name nihms797607t6.jpg JackiePhos 95 100 45
7 graphic file with name nihms797607t7.jpg BrettPhos 95 100 73 (68)
8 graphic file with name nihms797607t8.jpg BrettPhos 40 32 5
9 graphic file with name nihms797607t9.jpg BrettPhos 70 65 70
10c graphic file with name nihms797607t10.jpg BrettPhos 95 100 quant.
a

Conditions: 1.0 equiv 4a, 1.0 equiv amine, 1.4 equiv LiOtBu, 4 mol % Pd(OAc)2, 10 mol % ligand, PhCF3 (0.1 M), 95 °C, 16 h.

b

Determined by 1H NMR using phenanthrene as an internal standard. Isolated yields are given in parentheses.

c

1.0 equiv of 2-allylphenyl triflate and 1.2 equiv of pyrrolidine were used.