Synthesis of 4-vinylbiphenyl derivatives
Table 2. Pd-catalyzed Suzuki coupling of aryl bromides and arylboronic acidsa
Entry
1/R1
2/R2
Product
Time (min)
Yieldb (%)
1
4-Ethenyl (1a)
4-Me (2b)
4-C3H7 (2c)
4-OMe (2d)
4-CF3 (2e)
4-F (2f)
3b
3c
3d
3e
3f
30
10
10
10
30
30
10
20
10
10
10
10
10
10
10
10
10
20
10
10
10
10
83
86
90
81
80
83
86
85
70
74
92
98
82
82
90
81
76
65
70
96
95
92
2
1a
3
1a
4
1a
5
1a
6
1a
2,4,5-F3 (2g)
2-Me (2h)
3g
3h
3i
7
1a
8
1a
4-([1,1′-Biphenyl]-4-yl) (2i)
9
1a
4-(2-Naphthyl) (2j)
3j
10
11
12
13
14
15
16
17
18
19
20
21
22
1a
4-Ethenyl (2k)
3k
3b
3d
3i
4-Me (1b)
4-OMe (1c)
4-Ph (1d)
4-COMe (1e)
4-CN (1f)
4-NH2 (1g)
2k
2k
2k
2k
2k
2k
2k
2k
2k
2k
2k
2k
3l
3m
3n
3o
3p
3q
3r
3-bromopyridine (1h)
2-bromopyridine (1i)
2-bromothiophene (1j)
4-(4-propylcyclohexyl) (1k)
4-(4-pentylcyclohexyl) (1l)
4-[4’-pentyl-1,1’-bi(cyclohexyl)] (1m)
3s
3t
aReaction conditions: 1 (0.5 mmol), 2 (0.75 mmol), Pd(OAc)2 (0.5 mol%), PCy3 (1.0 mol%), K3PO4.3H2O (3.0 equiv.), toluene (2.0 ml); 80°C.
bIsolated yields.
Conclusions
References
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In summary, we have developed a rapid and efficient catalyst sys-
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PCy3-catalyzed Suzuki–Miyaura reactions in good to excellent yields
under mild conditions. With a simple reaction procedure and broad
available substrate range, this method was particularly useful for the
efficient preparation of 4-vinylbiphenyl functional monomers and
liquid crystal compounds.
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We gratefully acknowledge financial support of this work by the
National Basic Research Program of China (973 Program:
2012CB722603), the Program for Changjiang Scholars and
Innovative Research Team in University (No. IRT1161), the NSFC
(No. 21103114) and the Doctor Foundation of Xinjiang Bingtuan
(No. 2012BB010).
Appl. Organometal. Chem. (2013)
Copyright © 2013 John Wiley & Sons, Ltd.
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