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. Author manuscript; available in PMC: 2009 Jul 13.
Published in final edited form as: European J Org Chem. 2008;(31):5254–5262. doi: 10.1002/ejoc.200800651

Table 1.

Domino Heck–aza-Michael.[a]

graphic file with name nihms-116068-f0003.jpg
Entry Catalyst Base Additive % Conv.[b]
1 Pd(OAc)2/PPh3 Et3N – 34
2 Pd(OAc)2/PPh3 Cs2CO3 – 15
3 PdCl2(PPh)3 Cs2CO3 – 13
4 Pd2(dba)3·CHCl3 Et3N – 35
5 Pd(OAc)2/PPh3 Et3N Bu4NCl 91
6 Pd2(dba)3·CHCl3 Et3N Bu4NCl 95
7 Pd(OAc)2/PPh3 Et3N – 94[c]
8 Pd(OAc)2/PPh3 Et3N Bu4NCl 95[d]
[a]

Reaction conditions: 1 (0.12 mmol), Pd (2 mol-%), methyl acrylate (0.36 mmol), base (0.36 mmol) in DMF at 110 °C for 14 h.

[b]

Conversion by G.C.

[c]

Pd(OAc)2 (20 mol-%), PPh3 (40 mol-%) in microwave 110 °C for 2 h.

[d]

Pd(OAc)2 (10 mol-%), PPh3 (20 mol-%) in microwave 110 °C for 2 h.