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Synthesis of 4-substituted styrene compounds via palladium catalyzed SuzukiЦMiyaura reaction using bidentate Schiff base ligands.

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Full Paper
Received: 5 May 2009
Revised: 5 August 2009
Accepted: 5 August 2009
Published online in Wiley Interscience 16 September 2009
(www.interscience.com) DOI 10.1002/aoc.1548
Synthesis of 4-substituted styrene compounds
via palladium catalyzed Suzuki?Miyaura
reaction using bidentate Schiff base ligands
Yan Liu and Jinqu Wang?
Air-stable symmetric Schiff base have been synthesized and proved to be efficient ligands for Suzuki?Miyaura reaction between
aryl bromides and arylboronic acids using PdCl2 (CH3 CN)2 as palladium source under aerobic conditions. The coupling reaction
proceeded smoothly using N,N-bis(anthracen-9-ylmethylene)benzene-1,2-diamine (L7 ) as ligand to provide 4-substituted
c 2009 John Wiley & Sons, Ltd.
styrene compounds in good yields. Copyright Keywords: Suzuki?Miyaura reaction; Schiff base; 4-substituted styrene compounds; synthesis
Introduction
476
Substituted styrene starting materials have been extensively
used in both specialty chemical and polymer synthesis. Not
only can styrene be used in transformations such as olefin
metathesis[1] or Heck-type reactions[2] but also the alkene can
be employed as a platform on which to introduce a variety of
functionalities.[3 ? 8] In regard to polymer synthesis, a multitude
of transformations exist for polymerizing styrene.[9 ? 13] The
utility of such transformations has dramatically increased the
demand for facile routes to substituted styrene. Transition metalmediated cross-coupling reactions provide efficient routes to
functionalized styrene that complement traditional methods such
as dehydration,[14,15] Grignard reaction[16] or Hoffman elimination,
all of which are incompatible with sensitive functional groups. The
Suzuki?Miyaura reaction of organoboron compounds is nowadays
the most widely used cross-coupling reaction because of its low
toxicity and wide functional group tolerance,[17 ? 21] and has been
extensively used in the synthesis of pharmaceuticals,[22,23] and
liquid crystal compounds.[24 ? 29] Since the general procedures
were discovered, efforts have been made towards increasing
the substrate scope and efficiency. Therefore, designing ligands
with appropriate features and great diversity is crucial in dealing
with the challenging substrates in this area. For many years,
phosphine ligands have been most commonly employed for the
reaction. However, these types of ligands are generally either
air/moisture sensitive or expensive, which places significant
limits on their synthetic applications. Therefore, N-ligands,
which are inexpensive, easy to access and stable, have gained
major attention, such as Schiff bases,[30 ? 36] aryloximes,[37,38]
arylimines,[39 ? 45] N-acylamidines[46] , guanidine[47] and simple
amines.[48 ? 53] As a part of our ongoing efforts to develop efficient
methods for the synthesis of substituted styrene compounds,
herein we report the results of palladium-catalyzed coupling
reaction between aryl bromides and arylboronic acids to prepare
4-substituted styrene compounds by using symmetric Schiff base
as ligands in air.
Appl. Organometal. Chem. 2009 , 23, 476?480
H2 N
NH2 + R CHO
N
EtOH
R
N
N
R
L1: R = C6H5
L2: R = (4-Cl)C6H4
L3: R = (4-OMe)C6H4
L4: R = (2-OMe)C6H4
L5: R = (3-OMe,4-OMe)C6H4
N
L6 : R =
L7
Scheme 1. Synthesis of L1 ?L7 .
Results and Discussion
Ligands 1?7 were prepared by reaction of 1, 2-diamine with 2.0
equiv substituted aromatic aldehyde of in ethanol or MeOH/DMF,
they were used without further purification, and their structures
were established by 1 H NMR (Scheme 1). Initially, we focused on
optimization of the reaction conditions of the coupling reaction
of 4-bromostyrene with phenylboronic acid. The base usually
plays an important role in the Suzuki?Miyaura reaction (Table 1).
K3 PO4 �2 O gave the best results at a 40% yield (Table 1, entry
6). The contrast in yield for simple changes in base was more
profound for K3 PO4 �2 O and K3 PO4 (40 vs 30%, entries 5 and 6).
When K2 CO3 and CH3 ONa were used as base, the yield of product
was reduced to 29 and 31% respectively (Table 1, entries 3 and 4),
but Na2 CO3 and NaOH were no more efficient (Table 1, entries 1
and 2).
To evaluate the efficiency of PdCl2 (CH3 CN)2 ?ligands in the
Suzuki?Miyaura reaction, the coupling of 4-bromostyrene with
phenylboronic acid was tested, and the results are summarized
in Table 2. Among these ligands investigated, L1 ?L6 showed low
?
Correspondence to: Jinqu Wang, State Key Laboratory of Fine Chemicals, Institute of Adsorption and Inorganic Membrane, Dalian University of Technology,
158 Zhongshan Rd, Dalian 116012, China. E-mail: wangjinqu@hotmail.com
State Key Laboratory of Fine Chemicals, Institute of Adsorption and Inorganic
Membranes, Dalian 116012, People?s Republic of China
c 2009 John Wiley & Sons, Ltd.
Copyright Synthesis of 4-substituted styrene compounds
Table 1. Effect of base on the Suzuki?Miyaura reactiona
Entry
1
2
3
4
5
6
Base
Yield (%)b
Na2 CO3
NaOH
K2 CO3
MeONa
K3 PO4
K3 PO4 �2 O
trace
trace
29
31
30
40
a
Reaction conditions: p-bromostyrene (0.50 mmol), phenylboronic
acid (0.75 mmol), PdCl2 (CH3 CN)2 (0.50 mmol%), L6 (0.75 mmol%), base
(1.50 mmol), toluene (2.0 mL), 80 ? C, reaction time 10 h.
b Isolated yield.
(88?92%, Table 3, entries 13?15). In addition, aryl iodide such as
4-iodoacetophenone reacted with 4-vinylphenylboronic acid to
give excellent yield at 80 ? C (90%, Table 3, entry 16). However, aryl
chlorides such as 4-chloroacetophenone resulted in no reaction in
the same conditions (Table 3, entry 17).
Conclusion
In conclusion, symmetric Schiff base compounds (L1 ?L7 ) were easily prepared from commercially available reagents and show high
air-, moisture- and thermostability. We successfully synthesized 4substituted styrene compounds by Pd-catalyzed Suzuki?Miyaura
reaction of various aryl bromides with arylboronic acids using L7 as
ligand in air and provided a practical procedure for the synthesis
of liquid crystal compounds.
Table 2. Effect of ligand on the Suzuki?Miyaura reactiona
Entry
1
2
3
4
5
6
7
8
9
10
Ligand
Yield (%)b
?
L1
L2
L3
L4
L5
L6
L7
L7
L7
5
30
35
48
19
16
40
75
66c
70d
Experimental
General
1
H and 13 C NMR spectra were recorded on a 400 MHz spectrometer
with the chemical shift values reported in ? units (ppm) relative
to an internal standard (TMS). The open-bed chromatography was
carried out on silica gel (200?300 mesh, Qingdao Haiyang) using
gravity flow. The column was packed with slurries made from the
elution solvent.
Synthesis of L1 ?L7
a
Reaction conditions: p-bromostyrene (0.50 mmol), phenylboronic
acid (0.75 mmol), PdCl2 (CH3 CN)2 (0.50 mmol%), L1 ?L7 (0.75 mmol%),
K3 PO4 �2 O (1.50 mmol), toluene (2.0 mL), 80 ? C, reaction time 10 h.
b Isolated yield.
c
Pd(OAc)2 as Pd source.
d Pd (dba) 稢HCl as Pd source.
2
3
3
L1 ?L5 were synthesized according to the literature method.[54]
L6 and L7 were also synthesized according to the literature
method.[55] They were used without further purification.
Dibenzylidene ethylenediamine (L1 )[54]
Appl. Organometal. Chem. 2009, 23, 476?480
Yield: 67%. Yellow solid. M.p. 150?152 ? C. 1 H NMR (400 MHz,
CDCl3 ): ? 8.29 (s, 2H, H2 and H2 ), 7.71?7.68 (m, 4H, H3 and H3 ),
7.40?7.38 (m, 6H, H4, H4 and H5, H5 ), 3.98 (s, 4H, H1 and H1 ).
N,N-bis(4-chlorobenzylidene)ethane-1,2-diamine (L2 )[54]
Yield: 83%. White solid. M.p. 146?147 ? C. 1 H NMR (400 MHz, CDCl3 ):
? 8.23 (s, 2H, H2 and H2 ), 7.63 (d, J = 8.8 Hz, 4H, H3 and H3), 7.36
(d, J = 8.4 Hz, 4H, H4 and H4 ), 3.96 (s, 4H, H1 and H1 ).
N,N-bis(4-methoxybenzylidene)ethane-1,2-diamine (L3 )[54]
Yield: 78%. Yellow solid. M.p. 103?104 ? C. 1 H NMR (400 MHz,
CDCl3 ): ? 8.21 (s, 2H, H2 and H2 ), 7.63 (d, J = 8.8 Hz, 4H, H3 and
H3 ), 6.89 (d, J = 8.8 Hz, 4H, H4 and H4 ), 3.91 (s, 4H, H1 and
H1 ),3.77 (s, 6H, H5 and H5 ).
N,N-bis(2-methoxybenzylidene)ethane-1,2-diamine (L4 )[54]
Yield: 80%. White solid. M.p. 117?118 ? C. 1 H NMR (400 MHz, CDCl3 ):
? 8.71 (s, 2H, H2 and H2 ), 7.92 (d, J = 7.6 Hz, 2H, H3 and H3 ), 7.35
(t, J = 7.2, 8.4 Hz, 2H, H5 and H5 ), 6.96 (t, J = 7.2, 7.6 Hz, 2H, H6
and H6 ), 6.87 (d, J = 8.4 Hz, 2H, H4 and H4 ), 3.96 (s, 4H, H1 and
H1 ), 3.80 (s, 6H, H7 and H7 ).
c 2009 John Wiley & Sons, Ltd.
Copyright www.interscience.wiley.com/journal/aoc
477
efficiency, which gave the coupling product in 16?48% yield
(Table 2, entries 2?7). L7 showed good efficiency, and gave the
coupling product in 75% yield (Table 2, entry 8), but only a 5%
yield was obtained without any ligands (Table 2, entry 1). With
Pd(OAc)2 and Pd2 (dba)3 稢HCl3 as Pd sources, respectively, and L7
as ligand, the coupling product was also obtained in satisfactory
yields (66 and 70%, Table 2, entries 9 and 10).
Thus, the optimized reaction conditions for the Suzuki?Miyaura
reaction were PdCl2 (CH3 CN)2 (0.50% mmol), L7 (0.75% mmol)
and K3 PO4 �2 O (1.50 mmol) in toluene at 80 ? C. Next we
explored the scope of the coupling reaction in the presence
of a variety of functional groups. As shown in Table 3, the
Suzuki?Miyaura proceeds with good to excellent yields in the
presence of electron-poor functional groups including ketones
and aldehydes (80?92%, Table 3, entries 1, 3, 4, 5, 7, 9). However
the electron-rich aryl bromide, such as 4-bromoanisole reacted
with 4-vinylphenylboronic acid to give moderate yields at the same
conditions (68 and 70%, Table 3, entries 2 and 6). The aryl bromide
containing ortho substituent reacted to prepare the desired biaryl
product in moderate yield (51%, Table 3, entry 8), but electronpoor or -rich arylboronic acids reacted with p-bromostyrene to
give lower yields (40 and 47%, Table 3, entries 11, 12). The catalyst
system was also used to synthesize liquid crystal compounds
and obtained good yields at the optimized reaction conditions
Y. Liu and J. Wang
Table 3. Suzuki?Miyaura reaction of aryl halides and arylboronic acidsa
Entry
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
R1
X
R2
Product
Yield (%)b
4-Ethenyl (1a)
1a
1a
1a
1a
1a
1a
1a
1a
4-H (1b)
4-Me (1c)
4-F (1d)
1a
1a
1a
1a
1a
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
I
Cl
4-F (2a)
4-Me (2b)
4-Ethenyl (2c)
4-CHO (2d)
4-COMe (2e)
4-OMe (2f)
3,4-Difluoro (2g)
2,4,5-Trifluoro (2h)
3,4,5-Trifluoro (2i)
4-Ethenyl (2c)
4-Ethenyl (2c)
4-Ethenyl (2c)
4,4 -Propyl-cyclohexyl (2h)
4,4 -Pentyl-cyclohexyl (2i)
4,4 -Pentyl-bicyclohexyl (2n)
4-COMe (2l)
4-COMe (2m)
3a
3b
3c
3d
3e
3f
3g
3h
3i
3j
3b
3f
3k
3l
3m
3e
3e
81
70
92
80
87
68
86
51
87
75
40
47
92
90
88
90
0
Reaction conditions: aryl halides (0.50 mmol), arylboronic acids (0.75 mmol), PdCl2 (CH3 CN)2 (0.50 mmol%), L7 (0.75 mmol%), K3 PO4 �2 O
(1.50 mmol), toluene (2.0 mL), 80 ? C, reaction time 10 h.
b Isolated yield.
a
N,N-bis(3, 4-dimethoxybenzylidene)ethane-1,2-diamine (L5 )[55,57]
?
Yield: 75%. White solid. M.p. 155?156 C. 1 H NMR (400 MHz, CDCl3 ):
? 8.20 (s, 2H, H2 and H2 ), 7.40 (s, 2 H, H3 and H3 ), 7.11 (d, J = 8.4 Hz,
2H, H5 and H5 ), 6.86 (d, J = 8.0 Hz, 2H, H4 and H4 ), 3.93 (s, 10H,
H1, H1 and H6, H6 ), 3.91 (s, 6H, H7 and H7 ).
N,N-bis(9-anthrylmethylene)ethane-1,2-diamine (L6 )[56]
Yield: 92%.Yellow solid. M.p. 228?230 ? C. 1 H NMR (400 MHz,
CDCl3 ): ? 9.50 (s, 2H, H2 and H2 ), 8.46 (s, 2H, H7 and H7 ),
8.42 (d, J = 8.8 Hz, 4H, H3 and H3 ), 7.96 (d, J = 8.4 Hz, 4H, H4 and
H4 ), 7.36 (dd, J = 7.2, 8.0 Hz, 4H, H5 and H5 ), 7.12 (dd, J = 7.6,
8.0 Hz, 4H, H6 and H6 ), 4.52 (s, 4H, H1 and H1 ).
N,N-bis(9-anthrylmethylene)benzene-1,2-diamine (L7 )
Yield: 89%. Yellow solid. M.p. 168?170 ? C. 1 H NMR (400 MHz,
CDCl3 ): ? 9.80 (s, 2H, H3 and H3 ), 8.85 (d, J = 9.2 Hz, 4H, H4 and
H4 ), 8.50 (s, 2H, H8 and H8 ), 7.98 (d, J = 8.8 Hz, 4H, H5 and H5 ),
7.50?7.43 (m, 4H, H6 and H6 ), 7.37 (dd, J = 7.2, 7.6 Hz, 4H, H7 and
H7 ), 7.11 (dd, J = 7.6, 7.6 Hz, 4H, H1, H1 and H2, H2 ). 13 C NMR
(100 MHz, CDCl3 ): ? 121.2 (C3 and C3 ), 125.1 (C13 and C13 ), 125.5
(C1 and C1 ),126.9 (C9 and C9 ), 127.2 (C8 and C8 ), 128.9 (C10 and
C10 ), 130.7 (C7 and C7 ), 130.8 (C5 and C5 ), 131.4 (C2 and C2 ),
135.4 (C2 and C2 ), 145.7 (C12 and C12 ), 161.8 (C4 and C4 ). IR (KBr,
cm?1 ): 1623 (C N). Elemental anal. calcd for C36 H24 N2 : C, 89.23;
H, 4.99; N, 5.78. Found, C, 89.00; H, 5.00; N, 5.80.
Typical Suzuki?Miyaura reaction of aryl bromides
and arylboronic acids
478
To the solution of L7 (0.75% mmol) and PdCl2 (CH3 CN)2 (0.50%
mmol) in toluene (2.0 mL) were added aryl bromide (0.50 mmol),
www.interscience.wiley.com/journal/aoc
arylboronic acid (0.75 mmol) and K3 PO4 �2 O (1.50 mmol) under
air conditions. The mixture was sealed and was stirred at 80 ? C
for 10 h, cooled to room temperature and then shaken with
a mixture of water (4 mL) and EtOAc (4 mL). The organic layer
was separated, and the remaining aqueous phase was extracted
with EtOAc (2 � 5 mL). The combined organic extracts were
concentrated in vacuum, and the product was purified by flash
column chromatography on silica gel eluting with petroleum.
4-Fluoro-4 -vinylbiphenyl (3a)[62]
White solid. M.p. 125?126 ? C. 1 H NMR (400 MHz, CDCl3 ):
? 7.53?7.47 (m, 6H, H3?H5 and H3 ?H5 ), 7.15?7.10 (m, 2H, H6
and H6 ), 6.75 (dd, J = 10.8, 17.6 Hz, 1H, H2), 5.80 (d, J = 17.6 Hz,
1H, H1 ), 5.28 (d, J = 11.6 Hz, 1H, H1). 13 C NMR (100 MHz, CDCl3 ): ?
114.2 (C1), 115.7 (C9), 115.9 (C9 ), 126.9 (C4 and C4 ), 127.3 (C5 and
C5 ), 128.6 (C8 and C8 ), 128.7 (C7), 136.5 (C2), 136.8 (C6), 161.4
(C10).
4-Methyl-4 -vinylbiphenyl (3b)[58,62]
White solid. M.p. 119?120 ? C. 1 H NMR (400 MHz, CDCl3 ):
? 7.49?7.45 (m, 8H, H3?H6), 6.75 (dd, J = 10.8, 17.6 Hz, 1H,
H2), 5.79 (d, J = 17.6 Hz, 1H, H1), 5.27 (d, J = 10.8 Hz, 1H, H1 ),
2.39 (s, 3H, H7). 13 C NMR (100 MHz, CDCl3 ): ? 21.3 (C11), 113.8 (C1),
126.8 (C4 and C4 ), 127.0 (C5 and C5 ), 127.6 (C8 and C8 ), 129.7 (C9
and C9 ), 136.5 (C10), 136.6 (C2), 136.8 (C3), 138.02 (C7), 140.7 (C6).
4,4 -Diethenyl-1,1 -biphenyl (3c)[59]
White solid. M.p. 153 ? C. 1 H NMR (400 MHz, CDCl3 ): ? 7.57
(d, J = 8.4 Hz, 2H, H4 and H4 ), 7.48 (d, J = 8.4 Hz, 2H, H3
and H3 ), 6.75 (dd, J = 11.0, 17.6 Hz, 1H, H2), 5.80 (d, J = 17.6 Hz,
c 2009 John Wiley & Sons, Ltd.
Copyright Appl. Organometal. Chem. 2009, 23, 476?480
Synthesis of 4-substituted styrene compounds
1H, H1), 5.28 (d, J = 11.0 Hz, 1H, H1 ). 13 C NMR (100 MHz, CDCl3 ): ?
114.1 (C1), 126.8 (C4 and C4 ), 127.2 (C5 and C5 ), 136.5 (C2), 136.8
(C3), 140.2 (C6).
4 -Ethenyl-[1,1 -biphenyl]-4-carboxaldehyde (3d)[60]
White solid. M.p. 131?133 ? C. 1 H NMR (400 MHz, CDCl3 ): ? 10.06
(s, 1H, H7), 7.95 (d, J = 8.4 Hz, 2H, H6 and H6 ), 7.76 (d, J = 8.4 Hz,
2H, H5 and H5 ), 7.62 (d, J = 8.4 Hz, 2H, H4 and H4 ), 7.52 (d,
J = 8.4 Hz, 2H, H3 and H3 ), 6.77 (dd, J = 10.8, 17.6 Hz, 1H, H2),
5.83 (d, J = 17.6 Hz, 1H, H1), 5.33 (d, J = 10.8 Hz, 1H, H1 ). 13 C
NMR (100 MHz, CDCl3 ) ? 114.9 (C1), 127.0 (C4 and C4 ), 127.6 (C5
and C5 ), 127.7 (C8 and C8), 130.5 (C9 and C9 ), 135.4 (C10), 136.3
(C2), 138.0 (C6), 139.1 (C6), 146.8 (C7), 192.0 (C11).
1-[4 -Ethenyl (1, 1 -biphenyl)-4-yl]-ethanone (3e)[61]
White solid. M.p. 134?136 ? C. 1 H NMR (400 MHz, CDCl3 ): ? 8.03 (d,
J = 6.8 Hz, 2H, H6 and H6 ), 7.70 (d, J = 6.8 Hz, 2H, H5 and H5 ),
7.61 (d, J = 6.8 Hz, 2H, H4 and H4 ), 7.52 (d, J = 8.0 Hz, 2H, H3
and H3 ), 6.77 (dd, J = 10.8, 18.4 Hz, 1H, H2), 5.83 (d, J = 18.4 Hz,
1H, H1), 5.32 (d, J = 10.8 Hz, 1H, H1 ), 2.64 (s, 3H, H7). 13 C NMR
(100 MHz, CDCl3 ): ? 26.8 (C12), 114.7 (C1), 126.9 (C4 and C4 ), 127.1
(C5 and C5 ), 127.5 (C8 and C8 ), 129.1 (C9 and C9 ), 136.0 (C10),
136.3 (C2), 137.7 (CC3), 139.3 (C6), 145.4 (C7), 197.8 (C11).
4-Methoxy-4 -vinylbiphenyl (3f)[62]
White solid. M.p. 145?146 ? C. 1 H NMR (400 MHz, CDCl3 ): ? 7.48 (d,
J = 8.8 Hz, 2H, H5 and H5 ), 7.44 (d, J = 8.4 Hz, 2H, H4 and H4 ),
7.24 (d, J = 8.4 Hz, 2H, H3 and H3 ), 7.18 (d, J = 8.0 Hz, 2H, H6
and H6 ), 6.66 (dd, J = 11.0, 18.0 Hz, 1H, H2), 5.68 (d, J = 18.0 Hz,
1H, H1), 5.18 (d, J = 11.0 Hz, 1H, H1 ), 3.74 (s, 3H, H7). 13 C NMR
(100 MHz, CDCl3 ): ? 55.3 (C11), 113.5 (C1), 114.2 (C9 and C9 ), 126.6
(C4 and C4 ), 126.7 (C5 and C5 ), 127.9 (C8 and C8 ), 133.2 (C7),
136.0 (C2), 136.4 (C3), 140.2 (C6), 159.2 (C10).
3,4-Difluoro-4 -vinylbiphenyl (3g)
White solid. M.p. 39?40 ? C. Anal. calcd for C14 H9 F3 : C, 77.77; H, 4.66.
Found: C, 77.53; H, 4.85. 1 H NMR (400 MHz, CDCl3 ): ? 7.31?7.12
(m, 7H, H3?H7), 6.75 (dd, J = 11.6, 18.4 Hz, 1H, H2), 5.80 (d,
J = 18.4 Hz, 1H, H1), 5.30 (d, J = 11.6 Hz, 1H, H1 ); 13 C NMR
(100 MHz, CDCl3 ): ? 114.6 (C1), 115.9 (C11), 116.0 (C11), 117.6 (C8),
117.8 (C8), 127.0 (C4), 127.2 (C4 ), 136.3 (C5), 137.3 (C5 ), 138.6 (C3),
149.0 (C7), 149.6 (C6), 151.3 (C10), 152.0 (C9).
2,4,5-Trifluoro-4 -vinylbiphenyl (3h)
Appl. Organometal. Chem. 2009, 23, 476?480
White solid. M.p. 30?31 ? C. Anal. calcd for C14 H9 F3 : C, 71.79; H, 3.87.
Found: C, 71.85; H, 3.78. 1 H NMR (400 MHz, CDCl3 ): ? 7.49?7.45
(m, 4H, H3, H3 , H4 and H4 ), 7.21?7.17 (m, 2H, H5 and H5 ), 6.75
(dd, J = 10.8, 17.6 Hz, 1H, H2), 5.81 (d, J = 17.6 Hz, 1H, H1), 5.32
(d, J = 10.8 Hz, 1H, H1 ); 13 C NMR (100 MHz, CDCl3 ): ? 110.9 (C1),
111.1 (C8 and C8 ), 115.0 (C4 and C4 ), 127.1 (C5 and C5 ), 136.2
(C2), 137.6 (C7), 138.0 (C3), 140.7 (C10), 150.5 (C6), 153.0 (C9 and
C9 ).
4-Vinylbiphenyl (3j)[59]
White solid. M.p. 115 ? C. 1 H NMR (400 MHz, CDCl3 ): ? 7.61?7.22
(m, 9H, H3?H7), 6.76 (dd, J = 10.8, 17.6 Hz, 1H, H2), 5.79 (d,
J = 17.6 Hz, 1H, H1), 5.27 (d, J = 10.8 Hz, 1H, H1 ). 13 C NMR
(100 MHz, CDCl3 ): ? 114.0 (C1), 126.8 (C4 and C4 ), 127.1 (C10),
127.3 (C5 and C5 ), 127.4 (C8 and C8 ), 128.9 (C9 and C9 ), 136.6
(C2), 136.7 (C3), 140.7 (C6), 140.9 (C7).
4-Ethenyl-4 -(4-propylcyclohexyl)-1,1 -biphenyl (3k)
White solid. M.p. 60?62 ? C. Anal. calcd for C23 H28 : C, 90.73; H, 9.27.
Found: C, 90.48; H, 9.43. 1 H NMR (400 MHz, CDCl3 ): ? 7.59?7.46 (m,
6H, H3?H5 and H3 ?H5 ), 7.28 (d, J = 8.0 Hz, 2H, H6 and H6 ), 6.75
(dd, J = 10.8, 17.6 Hz, 1H, H2), 5.78 (d, J = 17.6 Hz, 1H, H1), 5.26 (d,
J = 10.8 Hz, 1H, H1 ), 2.49 (m, 1H, H7), 1.94?0.89 (m, 16H, H8, H8 ,
H9, H9 , and H10?H13); 13 C NMR (100 MHz, CDCl3 ): ? 14.6 (C17),
20.2 (C16), 33.8 (C14), 34.6 (C13 and C13 ), 37.3 (C12 and C12 ), 40.0
(C15), 44.5 (C11), 113.8 (C1), 126.8 (C4 and C4 ), 127.0 (C8 and C8 ),
127.3 (C5 and C5 ), 127.5 (C9 and C9 ), 136.5 (C2), 136.7 (C3), 138.5
(C7), 140.8 (C6), 147.4 (C10).
4-Ethenyl-4 -(4-pentylcyclohexyl)-1,1 -biphenyl (3l)
White solid. M.p. 140?142 ? C. Anal. calcd for C25 H32 : C, 90.30; H,
9.70. Found: C, 90.23; H, 9.68. 1 H NMR (400 MHz, CDCl3 ): ? 7.59?7.07
(m, 8H, H3?H6 and H3 ?H6 ), 6.75 (dd, J = 10.8, 17.6 Hz, 1H, H2),
5.78 (d, J = 17.6 Hz, 1H, H1), 5.26 (d, J = 10.8 Hz, 1H, H1 ),
2.54?0.84 (m, 15H, H7?H15). 13 C NMR (100 MHz, CDCl3 ): ? 14.3
(C19), 22.9 (C18), 26.9 (C16), 32.4 (C14), 33.8 (C12 and C12 ), 34.5
(C13 and C13 ), 37.5 (C17), 40.1 (C15), 44.5 (C11), 113.8 (C1), 126.8
(C4 and C4 ), 127.0 (C8 and C8 )), 127.2 (C5 and C5 ), 127.5 (C9 and
C9 ), 131.5 (C2), 136.5 (C3), 138.4 (C7), 140.8 (C6), 147.4 (C10).
4-Ethenyl-4 -[4 -pentyl(1,1 -bicyclohexyl)-4-yl]-1,1 -biphenyl (3m)
White solid. M.p. 170?172 ? C. Anal. calcd for C31 H42 : C, 89.79;
H, 10.21. Found: C, 89.84; H, 10.15. 1 H NMR (400 MHz, CDCl3 ): ?
7.59?7.27 (m, 8H, H3?H6 and H3 ?H6 ), 6.75 (dd, J = 11.2, 17.6 Hz,
1H, H2), 5.80 (d, J = 18.0 Hz, 1H, H1), 5.28 (d, J = 10.8 Hz, 1H, H1 ),
2.47(m, 1H, H7), 1.97?0.82 (m, 29H, H8?H19); 13 C NMR (100 MHz,
CDCl3 ): ? 14.3 (C23), 22.9 (C22), 26.9 (C13), 30.4 (C17), 30.6 (C20),
32.5 (C18), 33.9 (C16), 34.8 (C12), 37.7 (C21), 38.2 (C19), 43.2 (C14),
43.7 (C15), 44.6(C11), 113.8 (C1), 126.8 (C4 and C4 ), 127.0 (C8 and
C8 ), 127.2 (C5 and C5 ), 127.5 (C9 and C9 ), 136.5 (C2), 136.7 (C3),
138.4 (C7), 140.8 (C6), 147.4 (C10).
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c 2009 John Wiley & Sons, Ltd.
Copyright www.interscience.wiley.com/journal/aoc
479
White solid. M.p. 130?132 ? C. Anal. calcd for C14 H9 F3 : C, 71.79;
H, 3.87. Found: C, 71.60; H, 3.96. 1 H NMR (400 MHz, CDCl3 ): ?
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(d, J = 17.6 Hz, 1H, H1), 5.31 (d, J = 10.8 Hz, 1H, H1 ). 13 C NMR
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