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. Author manuscript; available in PMC: 2012 Oct 21.
Published in final edited form as: Org Lett. 2011 Sep 22;13(20):5413–5415. doi: 10.1021/ol202202a

Table 2.

Substrate Scope of Hiyama Coupling Reactions

graphic file with name nihms328264u3.jpg
entrya enaminone product yield (%)b
1 graphic file with name nihms328264t1.jpg
1a
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3b
85
2 graphic file with name nihms328264t3.jpg
1a
graphic file with name nihms328264t4.jpg
3c
73
3 graphic file with name nihms328264t5.jpg
1a
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3d
50
4 graphic file with name nihms328264t7.jpg
1a
graphic file with name nihms328264t8.jpg
3e
65
5 graphic file with name nihms328264t9.jpg
1a
graphic file with name nihms328264t10.jpg
3f
61
6c graphic file with name nihms328264t11.jpg
1a
graphic file with name nihms328264t12.jpg
3g
43
7 graphic file with name nihms328264t13.jpg
1b
graphic file with name nihms328264t14.jpg
3h
62
8 graphic file with name nihms328264t15.jpg
1c
graphic file with name nihms328264t16.jpg
3i
81
9 graphic file with name nihms328264t17.jpg
1d
graphic file with name nihms328264t18.jpg
3j
75
10 graphic file with name nihms328264t19.jpg
1e
graphic file with name nihms328264t20.jpg
3k
68
11 graphic file with name nihms328264t21.jpg
1f
graphic file with name nihms328264t22.jpg
3l
72
12d graphic file with name nihms328264t23.jpg
1g
not observed 0
13d graphic file with name nihms328264t24.jpg
1h
not observed 0
a

Reaction conditions: enaminone (0.1 M), Pd(OAc)2 (0.25 equiv), CuF2 (2.5 equiv), ArSi(OEt)3 (2.5 equiv) in tBuOH/AcOH (4:1), 65 °C, 3h.

b

Isolated yield.

c

α-Naphthyltrimethoxysilane was used.

d

Starting material recovered.