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. Author manuscript; available in PMC: 2010 Sep 17.
Published in final edited form as: Org Lett. 2009 Sep 17;11(18):4076–4079. doi: 10.1021/ol901518g

Table 1.

Selected Reaction Conditions for Optimization Studies

graphic file with name nihms-140824-t0010.jpg
entry Pd/ligand solv. temp time isolated yield
1 Pd(OAc)2
PPh3 		DMF 100 °C 5 h 40%
2 Pd2(dba)3·CHCl3
PPh3 		DMF 100 °C 5 h 40%
3 Pd(dba)2
P(OPh)3 		DMF 100 °C 8 h 0%a
4 Pd(dba)2
rac-BINAP		 DMF 100 °C 4 h 51%
5 Pd(dba)2
PS-PPh3 		DMF 100 °C 4 h 56%
6 Pd(dba)2
dppe		 DMF 100 °C 4 h 60%
7 Pd(dba)2
dppe b 		THF 75 °C 6 hc 82%
8 no palladium
no ligand		 DMF 145 °C 16 h 0%a
a

Starting material was recovered.

b

Reaction conducted with 5 mol % Pd(dba)2 and 15 mol % dppe resulted in 50% conversion to product (by1H NMR integration) after 6 h.

c

Longer reactions time (16 h) resulted in lower yield (53%).