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. Author manuscript; available in PMC: 2016 Feb 20.
Published in final edited form as: Org Lett. 2015 Feb 10;17(4):892–895. doi: 10.1021/ol503748t

Table 1.

Condition Optimizationa.

graphic file with name nihms-743914-t0002.jpg
entry Pd cat. x y solvent ligand base yield
(%)b
1 Pd(dba)2 1.5 5 DMF L1 - 54
2 Pd(dba)2 1.5 5 DMA L1 - 33
3 Pd(dba)2 1.5 5 DMF L1 - 49c
4 Pd(dba)2 1.5 5 DMF L1 Et3N -
5 Pd(dba)2 1.5 5 DMF L1 K2CO3 -
6 Pd(dba)2 2.0 5 DMF L1 - 73
7 Pd(dba)2 2.5 5 DMF L1 - 71
8 Pd(dba)2 2.0 8 DMF L1 - 80
9 Pd(dba)2 2.0 10 DMF L1 - 85
10 Pd(dba)2 2.0 10 DMF L2 - 81
11 Pd(dba)2 2.0 10 DMF L3 - 54
12 Pd(dba)2 2.0 10 DMF L4 - 90
13 Pd(dba)2 2.0 10 DMF - - 54
14 Pd(OAc)2 2.0 10 DMF L4 - 55
15 PdCl2 2.0 10 DMF L4 - trace
16 Pd(PPh3)4 2.0 10 DMF L4 - trace
graphic file with name nihms-743914-t0003.jpg
a

General reaction conditions unless otherwise noted: A mixture of palladium catalyst and ligand in DMF was stirred at rt for 20 min under argon before 5a and 6a were added. The reaction mixture was stirred at rt and monitored by thin-layer chromatography.

b

Isolated reaction yield.

c

60°C.