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. Author manuscript; available in PMC: 2014 Sep 18.
Published in final edited form as: J Am Chem Soc. 2013 Sep 4;135(37):10.1021/ja4073172. doi: 10.1021/ja4073172

Table 1.

Reaction Optimization for Conversion of Tetralone Pivaloyl Oxime to 1-Aminonaphthalene (2)a

graphic file with name nihms522440t1.jpg
Entry palladium ligand additive % conv/ % yieldb
1 10% Pd(P(o-tol)3)2 50/ 24
2 5% Pd2(dba)3 56/ 23
3 10% Pd(PPh3)4 96/ 70
4 5% Pd2(dba)3 20% PPh3 99/ 63
5 5% Pd2(dba)3 20% PCy3 99/ 68
6 10% Pd(OAc)2 20% PCyp3 97/ 82
7 10% Pd(OAc)2 20% PCy3 97/ 80
8 10% Pd(OAc)2 20% PPh3 74/ 37
9 10% Pd(OAc)2 20% dppe 73/ 62
10 10% Pd(OAc)2 20% dppf 78/ 44
11 10% Pd(OAc)2 20% PCyp3 30% PivOH 99/ 87
a

Reaction condition of Entry 11: 1c (0.2 mmol), Pd(OAc)2 (0.02 mmol), tricyclopentylphosphine (0.04 mmol), PivOH (0.06 mmol), K2CO3 (0.8 mmol), toluene (2.2 mL).

b

1H NMR yield; internal standard = tetrachloroethane.