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. Author manuscript; available in PMC: 2011 Sep 3.
Published in final edited form as: Org Lett. 2010 Sep 3;12(17):3760–3763. doi: 10.1021/ol1013476

Table 1.

Effect of Reaction Conditions on Carbonylative Conjugate Additions to Chalconea

graphic file with name nihms227192u2.jpg
entry catalyst ligand additive % yield
1 5% Pd(PPh3)4 - TMSCl+LiCl 70
2 5% Pd(PPh3)4 - TMSCl 82
3 5% Pd(PPh3)4 - - N.R.
4 2.5% Pd2(dba)3 PPh3 TMSCl 85
5 2.5% Pd2(dba)3 PCy3 TMSCl 82
6 0.25% Pd2(dba)3 PPh3 TMSCl 86
7 0.25% Pd2(dba)3 PCy3 TMSCl 86
8 2.5% Pd2(dba)3 PCy3 TMSCl 83b
9 5% Ni(cod)2 PCy3 TMSCl N.R.
10 5% Pt(dba)3 PCy3 TMSCl 0
a

Reaction with 1.3 equiv Et2Zn, 2.3 equiv TMSCl, 1 atm CO, for 4 h. Subsequent to reaction, the mixture was quenched at 0 °C with acetic acid (1.5 equiv) and TBAF (1.5 equiv) for 10 minutes and then treated with saturated Na2CO3.

b

Reaction with 0.65 equivalents of Et2Zn.