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. Author manuscript; available in PMC: 2018 Jul 7.
Published in final edited form as: J Org Chem. 2017 Jun 15;82(13):6946–6957. doi: 10.1021/acs.joc.7b00550

Table 1.

Optimization of Nitropyrazole Arylation

graphic file with name nihms915498u2.jpg
entry ligand base T(°C) GC yield (%)a
1 PCy3 Cs2CO3 80 0
2 PtBu3 Cs2CO3 80 0
3 PPh3 Cs2CO3 80 0
4 X-Phos Cs2CO3 80 89
5 S-Phos Cs2CO3 80 88
6 dcype Cs2CO3 80 0
7 X-Phos K2CO3 80 87
8 X-Phos Cs2CO3 120 56
9b X-Phos Cs2CO3 80 0
10 none Cs2CO3 80 0
[a]

Calibrated GC yields against hexadecane as the internal standard.

[b]

Reaction without Pd(OAc)2 catalyst.