Selective Heck reaction of aryl bromides with cyclopent-2-en-1-one or cyclohex-2-en-1-one

Article abstract of DOI:10.1016/j.tet.2008.11.006

The selective Heck reaction of cyclopent-2-en-1-one or cyclohex-2-en-1-one with aryl bromides gives a simple access to the corresponding 3-arylcycloalk-2-en-1-ones. The choice of the base was found to be crucial to avoid the formation of 3-arylcyclopentan

Full text of DOI:10.1016/j.tet.2008.11.006

Tetrahedron 65 (2009) 489–495
Contents lists available at ScienceDirect
Tetrahedron
journal homepage: www.elsevier.com/locate/tet
Selective Heck reaction of aryl bromides with cyclopent-2-en-1-one or
cyclohex-2-en-1-one
,
a,
*
Yacoub Fall a, Henri Doucet b , Maurice Santelli
*
a Laboratoire de Synthe`se Organique, UMR 6263 CNRS and Universite´ d’Aix-Marseille, Faculte´ des Sciences de Saint Je´roˆme, Avenue Escadrille Normandie-Niemen,
13397 Marseille Cedex 20, France
b
´
Institut Sciences Chimiques de Rennes, UMR 6226 CNRS-Universite de Rennes, ‘Catalyse et Organometalliques’, Campus de Beaulieu, 35042 Rennes, France
a r t i c l e i n f o
a b s t r a c t
Article history:
The selective Heck reaction of cyclopent-2-en-1-one or cyclohex-2-en-1-one with aryl bromides gives
a simple access to the corresponding 3-arylcycloalk-2-en-1-ones. The choice of the base was found to be
crucial to avoid the formation of 3-arylcyclopentanones or 3-arylcyclohexanones as side-products. Using
KF as base, DMF as solvent and Pd(OAc)2 as catalyst, the target products were obtained in moderate to
good yields with a variety of aryl bromides. Substituents such as fluoro, trifluoromethyl, acetyl, benzoyl,
formyl, ester or nitrile on the aryl bromide are tolerated. Sterically congested aryl bromides or bromo-
pyridines can also be employed.
Received 29 September 2008
Received in revised form 3 November 2008
Accepted 4 November 2008
Available online 8 November 2008
Ó 2008 Elsevier Ltd. All rights reserved.
1. Introduction
observed the formation of this unexpected side-product in 30%
selectivity in the course of the intramolecular arylation of a 4-
3-Arylcycloalk-2-en-1-ones bearing various substituents on the
aromatic ring are useful building blocks in organic synthesis. The
Heck palladium catalyzed reaction of aryl and heteroaryl halides
with cycloalk-2-en-1-one should be a powerful method for the
synthesis of these compounds.1 However, if the Heck reaction of
aryl halides with linear alk-1-en-3-ones has been largely de-
scribed,2–4 on the other hand, only a few examples of coupling of
cyclopent-2-en-1-one or cyclohex-2-en-1-one with aryl halides
have been reported.2n,3i,5,6–10 Moreover, most of the results employ
aryl iodides, which are generally more expensive than aryl bromi-
des.2n,9,10 In most cases, the reaction of cycloalk-2-en-1-one with
aryl bromides led to moderate yields or to mixtures.3i,5 For exam-
ple, 2-bromo-6-dimethylaminonaphthalene reacted with cyclo-
pent-2-en-1-one or cyclohex-2-ene-1-one in the presence of
PdCl2(PPh3)2 as catalyst gave the desired products in 50 and 38%
yields, respectively.3i A similar yield was observed for the coupling
of 4-bromoanisole with cyclopent-2-en-1-one using Pd(OAc)2/
DABCO as catalyst and K2CO3 as base.5 In some cases, the formation
of the double bond hydrogenated by-product was obtained in rel-
atively large amount (Scheme 1). Negishi and co-workers had
substituted cyclohex-2-en-1-one.6 Genet and co-workers also
studied this reaction. They observed that for the coupling of iodo-
benzene with cyclohex-2-en-1-one using Pd(OAc)2/TPPTS as cata-
lyst, the ratio of desired Heck product and hydrogenated product
was 40:60.7 In a few other cases, expensive aryl iodides were also
employed for this reaction.2n,8–10 Myers and Tanaka have recently
reported the influence of some reaction conditions for the vinyl-
ation of 2,4-dimethoxyiodobenzene using cyclohex-2-en-1-one.8
The best yield was obtained using Pd(OAc)2 as catalyst, NaHCO3 as
base in the presence of a stoichiometric amount of Bu4NCl.
O
O
O
[Pd]
solvent, base
+
X
+
R
R
R
Scheme 1.
Therefore, the discovery of reaction conditions leading selec-
tively and in high yields to the 3-arylcycloalk-2-en-1-ones, espe-
cially in the presence of aryl bromides, which are more easily
available than iodides, and in absence of additives such as ammo-
nium salts, which are an important source of wastes, is desirable.
Here, in order to establish the requirements for a successful 3-
arylation of cyclopent-2-en-1-one or cyclohex-2-en-1-one, we
* Corresponding authors. Tel.: þ33 2 23 23 63 84; fax: þ33 2 23 23 69 39 (H.D.);
tel.: þ33 4 91 28 88 25 (M.S.).
E-mail addresses: henri.doucet@univ-rennes1.fr (H. Doucet), m.santelli@univ-
cezanne.fr (M. Santelli).
0040-4020/$ – see front matter Ó 2008 Elsevier Ltd. All rights reserved.
doi:10.1016/j.tet.2008.11.006

490
Y. Fall et al. / Tetrahedron 65 (2009) 489–495
wish to report on the influence of several reaction parameters and
also on the aryl bromide substitution, on the yields and
selectivities.
led to complete conversion of the aryl bromide, but no improve-
ment of the selectivity in 1a was observed (Table 1, entries 9 and
10). A lower reaction temperature (80 ꢀC) also led to a very low
conversion of the aryl bromide (Table 1, entry 11).
Then, using the most selective reaction condition (DMF, KF,
Pd(OAc)2, 130 ꢀC), we explored the scope and limitations of this
reaction using para-, meta- and ortho-substituted aryl bromides
and also a few heteroaryl bromides employing cyclopent-2-en-1-
one or cyclohex-2-en-1-one as vinylation partners (Schemes 3 and
4, Tables 2–5).
2. Results and discussion
For this study, based on previous results,4,11–13 DMF was initially
chosen as the solvent. The reactions were performed at 130 ꢀC
under argon in the presence Pd(OAc)2 as catalyst. First, we exam-
ined the influence of the base for the coupling of 4-bromoaceto-
phenone with cyclopent-2-en-1-one. Surprisingly, a very important
effect of the base was observed. In all cases, a complete conversion
of the aryl bromide was observed. However, the yield in target
product 1a strongly depends on the base. Using Cs2CO3 or t-BuOK,
no formation of 1a was detected by gas chromatography (Scheme 2,
Table 1, entries 1 and 2). A clean reaction was observed using
Na2CO3, but, in the presence of this base, the hydrogenated side-
product 1b was obtained in 81% selectivity (Table 1, entry 3). A
suitable conformation of the Pd intermediate is necessary for the
O
O
Pd(OAc)2
+
Br
DMF, KF, 130 °C, 20 h
R
R
2−17
Scheme 3.
b
-elimination step of the catalytic cycle. With cyclopent-2-en-1-
one, the conformation of the palladium intermediate is probably
not suitable for a fast -elimination, and side-reactions occur. A
O
O
b
Pd(OAc)2
+
R
Br
similar phenomenon had been observed for Heck reactions using
cyclopentene or cyclohexene. With these substrates, the partial
migration of the double bond of the cycloalkene was observed.13
Therefore, the formation of 1b using cyclopent-2-en-1-one was not
surprising. Then, we studied this reaction using other bases, and we
observed more selective reactions in favour of 1a in the presence of
K2CO3 or NaOAc (Table 1, entries 4 and 5). However, the best se-
lectivity in 1a was obtained employing KF as base with a ratio 1a/1b
of 88:12 (Table 1, entry 6). Using these conditions,1a was isolated in
62% yield.
DMF, KF, 130 °C, 20 h
R
18−31
Scheme 4.
First, we have investigated the reaction of cyclopent-2-en-1-
one with several para-substituted aryl bromides (Scheme 3, Table 2).
In most cases, the reaction proceeds very smoothly in the
O
O
Table 2
Palladium catalyzed reaction of cyclopent-2-en-1-one with para- or meta-
substituted aryl bromides (Scheme 3)
O
Pd(OAc)2
+
Br
+
solvent, base,
80−130 °C, 20 h
Entry
1
Aryl bromide
Product
Yield (%)
69
O
O
Br
O
O
O
O
1a
1b
2
Scheme 2.
O
Ph
Ph
2
3
71
61
Br
Br
Next, we examined the influence of the solvent on the conver-
sion and selectivity. Very low conversions of 4-bromoacetophenone
were observed in the presence of acetonitrile or 1,2-dimethoxy-
ethane (Table 1, entries 7 and 8). On the other hand, NMP or DMAc
O
O
3
O
O
O
MeO
NC
MeO
NC
4
Table 1
O
Influence of the reaction conditions for palladium catalyzed arylation of cyclopent-
2-en-1-one using 4-bromoacetophenone (Scheme 2)
4
5
73
67
Br
5
6
O
Entry Base
Solvent Temperature Conversion of
Ratio of Yield in
(ꢀC)
4-bromoacetophenone products 1a (%)
F3C
Br
F3C
(%)
1a/1b
1
2
3
4
5
6
7
Cs2CO3 DMF
130
130
130
130
130
130
100
100
100
100
100
100
0
d
0
0
12
4
41
66 (62)
0
O
t-BuOK DMF
Na2CO3 DMF
K2CO3 DMF
NaOAc DMF
d
6
7
68
58
F
Br
F
19/81
50/50
64/36
88/12
d
7
NC
NC
O
KF
DMF
Br
NaOAc MeCN 130
8
8
9
10
11
NaOAc DME
130
130
5
d
3
KF
KF
KF
NMP
DMAc 130
DMF 80
100
100
2
72/28
72/28
d
34
24
0
Br
O
8
70
9
Conditions: Pd(OAc)2 (0.02 equiv), 4-bromoacetophenone (1 equiv), cyclopent-2-
en-1-one (2 equiv), KF (2 equiv), DMF, 20 h, GC and NMR yields, yield in parenthesis
is isolated.
Conditions: Pd(OAc)2 (0.02 equiv), ArBr (1 equiv), cyclopent-2-en-1-one (2 equiv),
KF (2 equiv), DMF, 130 ꢀC, 20 h, isolated yields.

Y. Fall et al. / Tetrahedron 65 (2009) 489–495
491
Table 4
presence of 2 mol % catalyst. We observed that yields of 61–71%
can be obtained for activated substrates such as 4-bromopro-
piophenone, 4-bromobenzophenone, 4-bromobenzonitrile, 4-tri-
fluoromethylbromobenzene or 4-fluorobromobenzene (Table 2,
entries 1–6). The influence of the presence of meta-substituents
on the aryl bromide is also reported in Table 2. As expected
a relatively similar yield than in the presence of the para-
substituted substrates was observed with 3-bromobenzonitrile
(Table 2, entry 7). With the non-activated 2-bromonaphthalene,
a yield of 70% in 9 was obtained (Table 2, entry 8).
ortho-Substituents on the aryl bromides generally have a more
important effect on the reaction rates of Heck reactions due to their
steric or coordination properties. With cyclopent-2-en-1-one, in
some cases, similar yields than in the presence of the para-
substituted aryl bromides were obtained. We observed that the
coupling of 2-trifluoromethylbromobenzene or 1-bromonaph-
thalene proceeds nicely to give 10 and 13 in 64 and 77% yields,
respectively (Table 3, entries 1 and 4). On the other hand, 2-bro-
mobenzonitrile and methyl 2-bromobenzoate gave 11 and 12 in
lower yields of 48 and 46%, respectively, due to the formation of
unidentified side-products (Table 3, entries 2 and 3). Next, we tried
to evaluate the difference of reactivity between mono- and di-or-
tho-substituted aryl bromides, and we observed that even the
highly hindered aryl bromide, 9-bromoanthracene, could be
employed successfully (Table 3, entry 5).
Palladium catalyzed reaction of cyclohex-2-en-1-one with para- or meta-substituted
aryl bromides (Scheme 4)
Entry
1
Aryl bromide
Product
Yield (%)
55
O
Br
O
O
18
O
Br
2
3
4
5
6
7
8
57
50
53
48
64
51
46
O
O
19
O
O
O
H
O
H
Br
20
Ph
O
Ph
O
Br
21
O
O
O
Br
MeO
MeO
22
O
NC
Br
NC
23
NC
O
NC
Table 3
Br
Palladium catalyzed reaction of cyclopent-2-en-1-one with ortho-substituted aryl
bromides and heteroaryl bromides (Scheme 3)
24
O
O
O
Entry
1
Aryl bromide
Product
CF3
Yield (%)
64
O
O
Br
CF3
25
O
O
O
Br
10
11
12
O
Br
CN
CN
Br
9
55
2
3
4
48
46
77
26
Conditions: Pd(OAc)2 (0.02 equiv), ArBr (1 equiv), cyclohex-2-en-1-one (2 equiv), KF
(2 equiv), DMF, 130 ꢀC, 20 h, isolated yields.
CO2Me
CO2Me
Br
Then, we examined the reactivity of cyclohex-2-en-1-one with
a set of aryl bromides using the same reaction conditions (Scheme
4, Tables 4 and 5). The expected 3-arylcyclohex-2-en-1-ones 18–31
were obtained in moderate to good yields. In the presence of para-
substituted aryl bromides, compounds 18–23 have been isolated in
48–64% yields (Table 4, entries 1–6). The highest yield was obtained
using 4-bromobenzonitrile (Table 4, entry 6).
In all cases, the formation of the hydrogenated compounds and
also of several other minor side-products was observed. 3-Bro-
mobenzonitrile led to 24 in 51% yield (Table 4, entry 7). Non-acti-
vated aryl bromides, 4-bromo-1,2-(methylenedioxy)benzene and
2-bromonaphthalene also gave the target products 25 and 26 in
moderate yields (Table 4, entries 8 and 9). The two ortho-
substituted aryl bromides 2-bromobenzonitrile and 1-bromo-
naphthalene were found to give 27 and 28 in 39 and 51% yields,
respectively (Table 5, entries 1 and 2). Finally, three heteroaryl
bromides have been employed. 3-Bromopyridine, 3-bromoquino-
line or 4-bromoisoquinoline gave 29–31 in 56–60% yields (Table 5,
entries 3–5).
O
O
Br
Br
13
5
57
14
O
Br
6
7
68
60
N
N
15
O
Br
N
N
16
O
In summary, we have established that, using appropriate re-
action conditions, Pd(OAc)2 provides an efficient catalyst for the
coupling of aryl bromides with cyclopent-2-en-1-one or cyclohex-
2-en-1-one. The nature of the base has a determining influence on
the reaction yields and selectivities. In the presence of KF as base,
8
51
Br
N
N
17
Conditions: Pd(OAc)2 (0.02 equiv), ArBr (1 equiv), cyclopent-2-en-1-one (2 equiv),
KF (2 equiv), DMF, 130 ꢀC, 20 h, isolated yields.

492
Y. Fall et al. / Tetrahedron 65 (2009) 489–495
Table 5
3.3. 3-(4-Acetylphenyl)-cyclopent-2-enone (1a)
Palladium catalyzed reaction of cyclohex-2-en-1-one with ortho-substituted aryl
bromides and heteroaryl bromides (Scheme 4)
From 4-bromoacetophenone (0.199 g, 1 mmol) and cyclopent-2-
Entry
1
Aryl bromide
Product
Yield (%)
39
en-1-one, product 1 was obtained in 62% (0.124 g) yield.
1H NMR (200 MHz, CDCl3)
d
8.02 (d, J¼8.4 Hz, 2H), 7.73 (d,
J¼8.4 Hz, 2H), 6.64 (s, 1H), 3.07 (m, 2H), 2.63 (s, 3H), 2.58 (m, 2H);
13C NMR (50 MHz, CDCl3)
208.9, 197.2, 172.1, 138.6, 138.1, 129.4,
CN
O
CN
Br
d
27
128.8, 126.9, 35.3, 28.6, 26.7; C13H12O2: calcd C 77.98, H 6.04; found
C 77.90, H 6.15. Product 1b was also isolated in low yield: 1H NMR
O
O
2
3
4
51
56
59
(200 MHz, CDCl3)
3.50 (m, 1H), 2.80–1.97 (m, 9H).
d
7.98 (d, J¼8.4 Hz, 2H), 7.34 (d, J¼8.4 Hz, 2H),
Br
Br
28
3.4. 3-(4-Propionylphenyl)-cyclopent-2-enone (2)
N
29
N
From 4-bromopropiophenone (0.213 g, 1 mmol) and cyclopent-
2-en-1-one, product 2 was obtained in 69% (0.148 g) yield.
O
1H NMR (200 MHz, CDCl3)
d
8.01 (d, J¼8.4 Hz, 2H), 7.71 (d,
Br
J¼8.4 Hz, 2H), 6.62 (s, 1H), 3.05 (m, 2H), 2.99 (q, J¼7.5 Hz, 2H), 2.60
N
30
N
(m, 2H), 1.22 (t, J¼7.5 Hz, 3H); 13C NMR (50 MHz, CDCl3)
d 208.8,
199.8, 172.1, 138.4, 137.9, 129.1, 128.4, 126.9, 35.2, 32.0, 28.6, 8.04;
C14H14O2: calcd C 78.48, H 6.59; found C 78.61, H 6.39.
O
5
60
3.5. 3-(4-Benzoylphenyl)-cyclopent-2-enone (3)
Br
N
N
31
From 4-bromobenzophenone (0.261 g, 1 mmol) and cyclopent-
Conditions: Pd(OAc)2 (0.02 equiv), ArBr (1 equiv), cyclohex-2-en-1-one (2 equiv), KF
(2 equiv), DMF, 130 ꢀC, 20 h, isolated yields.
2-en-1-one, product 3 was obtained in 71% (0.186 g) yield.
1H NMR (200 MHz, CDCl3)
d
7.95–7.60 (m, 9H), 6.67 (s, 1H), 3.09
(m, 2H), 2.63 (m, 2H); 13C NMR (50 MHz, CDCl3)
d
208.9, 195.8,
the 3-arylcycloalk-2-en-1-ones were generally obtained in mod-
erate to high yields. A wide range of functions such as fluoro, acetyl,
formyl, benzoyl, carboxylate or nitrile on the aryl bromide are tol-
erated. Sterically hindered aryl bromides and some heteroaromatic
substrates such as bromopyridines have also been employed suc-
cessfully. It should be noted that, despite their interest, most of the
products prepared by this method are new, indicating a relatively
limited access to such compounds using more traditional cross-
coupling procedures. A very wide variety of aryl bromides, cyclo-
pent-2-en-1-one or cyclohex-2-en-1-one and also the catalyst are
commercially available. This is a practical advantage of this
reaction.
172.3, 139.5, 137.5, 137.0, 132.8, 130.4, 130.0, 129.2, 128.4, 126.6, 35.3,
28.7; C18H14O2: calcd C 82.42, H 5.38; found C 82.47, H 5.20.
3.6. 4-(3-Oxocyclopent-1-enyl)-benzoic acid methyl ester (4)
From methyl 4-bromobenzoate (0.215 g, 1 mmol) and cyclo-
pent-2-en-1-one, product 4 was obtained in 61% (0.132 g) yield.
1H NMR (200 MHz, CDCl3)
d
8.09 (d, J¼8.3 Hz, 2H), 7.70 (d,
J¼8.3 Hz, 2H), 6.63 (s, 1H), 3.94 (s, 3H), 3.06 (m, 2H), 2.60 (m, 2H);
13C NMR (50 MHz, CDCl3)
208.9, 172.3, 166.2, 138.0, 132.1, 130.0,
d
129.2, 126.7, 52.3, 35.3, 28.7; C13H12O3: calcd C 72.21, H 5.59; found
C 72.30, H 5.48.
3. Experimental
3.7. 4-(3-Oxocyclopent-1-enyl)-benzonitrile (5)
3.1. General remarks
From 4-bromobenzonitrile (0.182 g, 1 mmol) and cyclopent-2-
en-1-one, product 5 was obtained in 73% (0.134 g) yield.
All reactions were run under argon in Schlenk tubes using
vacuum lines. DMF analytical grade was not distilled before use.
KF (99%) was used. Commercial aryl bromides were used with-
out purification. The reactions were followed by GC and NMR.
1H NMR (200 MHz, CDCl3)
d
7.74 (m, 4H), 6.65 (s, 1H), 3.05 (m,
2H), 2.63 (m, 2H); 13C NMR (50 MHz, CDCl3)
d
208.5, 170.9, 138.1,
132.6, 130.1, 127.2, 118.1, 114.3, 35.3, 28.5; C12H9NO: calcd C 78.67, H
4.95; found C 78.51, H 5.07.
1H and 13C spectra were recorded with
a Bruker 200 MHz
spectrometer in CDCl3 solutions. Chemical shifts are reported in
parts per million relative to CDCl3 (7.25 for 1H NMR and 77.0 for
13C NMR). Flash chromatography was performed on silica gel
(230–400 mesh).
3.8. 3-(4-Trifluoromethylphenyl)-cyclopent-2-enone (6)
From 4-bromobenzotrifluoride (0.225 g, 1 mmol) and cyclo-
pent-2-en-1-one, product 6 was obtained in 67% (0.152 g) yield.
1H NMR (200 MHz, CDCl3)
d
7.90 (m, 4H), 6.65 (s, 1H), 3.05 (m,
3.2. General procedure
2H), 2.63 (m, 2H); 13C NMR (50 MHz, CDCl3)
d
208.8, 171.8, 132.7 (q,
J¼31.7 Hz), 129.3, 127.3, 126.0, 125.8 (q, J¼3.7 Hz), 124.6 (q,
J¼271.6 Hz), 35.3, 28.7; C12H9F3O: calcd C 63.72, H 4.01; found C
63.59, H 4.19.
In a typical experiment, the aryl halide (1 mmol), cyclopent-2-
en-1-one (0.164 g, 2 mmol) or cyclohex-2-en-1-one (0.192 g,
2 mmol), KF (0.116 g, 2 mmol), Pd(OAc)2 (0.005 g, 0.02 mmol), were
dissolved in DMF (5 mL) under an argon atmosphere. The reaction
mixture was stirred at 130 ꢀC for 18 h. Then, the product was
extracted three times with Et2O or CH2Cl2. The combined organic
layer was dried over MgSO4 and the solvent was removed in vacuo.
The crude product was purified by silica gel column
chromatography.
3.9. 3-(4-Fluorophenyl)-cyclopent-2-enone (7)
From 4-bromofluorobenzene (0.175 g, 1 mmol) and cyclopent-
2-en-1-one, product 7 was obtained in 68% (0.120 g) yield.
1H NMR (200 MHz, CDCl3)
(t, J¼8.7 Hz, 2H), 3.06 (m, 2H), 2.62 (m, 2H).
d
7.70 (dd, J¼5.3 and 8.7 Hz, 2H), 7.70

Y. Fall et al. / Tetrahedron 65 (2009) 489–495
493
3.10. 3-(3-Oxocyclopent-1-enyl)-benzonitrile (8)
1H NMR (200 MHz, CDCl3)
d
8.49 (s, 1H), 8.10–7.95 (m, 2H), 7.95–
7.85 (m, 2H), 7.60–7.40 (m, 4H), 6.49 (s, 1H), 3.13 (m, 2H), 2.83 (m,
From 3-bromobenzonitrile (0.182 g, 1 mmol) and cyclopent-2-
2H); 13C NMR (50 MHz, CDCl3)
d
209.4, 177.2, 136.0, 131.2, 131.0,
en-1-one, product 8 was obtained in 58% (0.106 g) yield.
128.7, 127.6, 127.3, 126.3, 125.4, 124.8, 35.7, 34.5; C19H14O: calcd C
88.34, H 5.46; found C 88.49, H 5.31.
1H NMR (200 MHz, CDCl3)
d
7.90 (s, 1H), 7.88 (d, J¼8.5 Hz, 1H),
7.75 (d, J¼8.5 Hz, 1H), 7.59 (t, J¼8.5 Hz, 1H), 3.04 (m, 2H), 2.62 (m,
2H); 13C NMR (50 MHz, CDCl3)
208.5, 170.6, 135.3, 134.0, 130.8,
d
3.17. 3-(Pyridin-3-yl)-cyclopent-2-enone (15)
130.0,129.8,129.3,118.0,113.4, 35.2, 28.5; C12H9NO: calcd C 78.67, H
4.95; found C 78.39, H 4.87.
From 3-bromopyridine (0.158 g, 1 mmol) and cyclopent-2-en-1-
one, product 15 was obtained in 68% (0.108 g) yield.
3.11. 3-(Naphthalen-2-yl)cyclopent-2-enone (9)
1H NMR (200 MHz, CDCl3)
d
8.90 (s, 1H), 8.68 (d, J¼4.2 Hz, 1H),
7.92 (d, J¼8.1 Hz, 1H), 7.40 (dd, J¼8.1 and 4.2 Hz, 1H), 6.63 (s, 1H),
3.07 (m, 2H), 2.62 (m, 2H); 13C NMR (50 MHz, CDCl3)
208.6, 170.4,
From 2-bromonaphthalene (0.207 g, 1 mmol) and cyclopent-2-
d
en-1-one, product 9 was obtained in 70% (0.146 g) yield.
151.8, 147.8, 133.8, 129.7, 128.7, 123.7, 35.0, 28.4; C10H9NO: calcd C
75.45, H 5.70; found C 75.50, H 5.56.
1H NMR (200 MHz, CDCl3)
d
8.05 (s, 1H), 8.00–7.88 (m, 3H), 7.70
(d, J¼8.0 Hz, 1H), 7.26 (m, 2H), 6.65 (s, 1H), 3.10 (m, 2H), 2.60 (m,
2H); 13C NMR (50 MHz, CDCl3)
209.2, 173.4, 134.4, 132.8, 131.2,
d
3.18. 3-(Quinolin-3-yl)-cyclopent-2-enone (16)
128.8,128.5,127.7 (2C),127.6,126.8 126.7,123.8, 35.1, 28.4; C15H12O:
calcd C 86.51, H 5.81; found C 86.59, H 5.69.
From 3-bromoquinoline (0.208 g, 1 mmol) and cyclopent-2-en-
1-one, product 16 was obtained in 60% (0.126 g) yield.
3.12. 3-(2-Trifluoromethylphenyl)-cyclopent-2-enone (10)
1H NMR (200 MHz, CDCl3)
d 9.18 (s, 1H), 8.32 (s, 1H), 8.14 (d,
J¼8.2 Hz, 1H), 7.89 (d, J¼8.2 Hz, 1H), 7.80 (t, J¼7.5 Hz, 1H), 7.60 (t,
From 2-bromobenzotrifluoride (0.225 g, 1 mmol) and cyclo-
J¼7.5 Hz, 1H), 6.76 (s, 1H), 3.16 (m, 2H), 2.62 (m, 2H); 13C NMR
pent-2-en-1-one, product 10 was obtained in 64% (0.145 g) yield.
(50 MHz, CDCl3) d 208.6, 170.2, 149.4, 148.5, 133.6, 131.1, 129.4,
128.6, 128.5, 127.6, 127.3, 126.9, 34.9, 28.4; C14H11NO: calcd C 80.36,
H 5.30; found C 80.52, H 5.27.
1H NMR (200 MHz, CDCl3)
d
7.74 (d, J¼8.0 Hz, 1H), 7.64–7.46 (m,
2H), 7.32 (d, J¼8.0 Hz, 1H), 6.24 (s, 1H), 2.97 (m, 2H), 2.61 (m, 2H);
13C NMR (50 MHz, CDCl3)
208.8, 174.4, 133.7, 131.7, 128.8, 128.2,
d
127.5 (q, J¼30.5 Hz), 126.4 (q, J¼5.2 Hz), 124.2 (q, J¼273.5 Hz), 35.5,
3.19. 3-(Isoquinolin-4-yl)-cyclopent-2-enone (17)
33.5; C12H9F3O: calcd C 63.72, H 4.01; found C 63.80, H 3.98.
From 4-bromoisoquinoline (0.208 g, 1 mmol) and cyclopent-2-
3.13. 2-(3-Oxocyclopent-1-enyl)-benzonitrile (11)
en-1-one, product 17 was obtained in 51% (0.107 g) yield.
1H NMR (200 MHz, CDCl3)
d
9.27 (s, 1H), 8.60 (s, 1H), 8.05–7.90
(m, 2H), 7.80–7.55 (m, 2H), 6.58 (s, 1H), 3.19 (m, 2H), 2.68 (m, 2H);
13C NMR (50 MHz, CDCl3)
208.6, 171.5, 154.2, 153.0, 144.0, 140.8,
From 2-bromobenzonitrile (0.182 g, 1 mmol) and cyclopent-2-
en-1-one, product 11 was obtained in 48% (0.088 g) yield.
d
1H NMR (200 MHz, CDCl3)
d
7.80 (d, J¼8.4 Hz, 1H), 7.85–7.30 (m,
3H), 6.83 (s, 1H), 3.16 (m, 2H), 2.63 (m, 2H); 13C NMR (50 MHz,
CDCl3) 208.4, 170.0, 137.9, 134.6, 133.2, 133.1, 130.2, 128.0, 118.0,
134.5, 131.5, 130.8, 128.4, 127.7, 123.6, 35.1, 32.3; C14H11NO: calcd C
80.36, H 5.30; found C 80.21, H 5.24.
d
110.4, 35.2, 30.4; C12H9NO: calcd C 78.67, H 4.95; found C 78.79, H
4.96.
3.20. 3-(4-Acetylphenyl)-cyclohex-2-enone (18)
From 4-bromoacetophenone (0.199 g, 1 mmol) and cyclohex-2-
3.14. Methyl 2-(3-oxocyclopent-1-enyl)-benzoate (12)
en-1-one, product 18 was obtained in 55% (0.118 g) yield.
1H NMR (200 MHz, CDCl3)
d
7.99 (d, J¼8.4 Hz, 2H), 7.61 (d,
From methyl 2-bromobenzoate (0.215 g, 1 mmol) and cyclo-
J¼8.4 Hz, 2H), 6.44 (s, 1H), 2.81 (t, J¼7.6 Hz, 2H), 2.62 (s, 3H), 2.53 (t,
pent-2-en-1-one, product 12 was obtained in 46% (0.099 g) yield.
J¼7.6 Hz, 2H), 2.24 (m, 2H); 13C NMR (50 MHz, CDCl3)
d 199.5, 197.3,
1H NMR (200 MHz, CDCl3)
d
7.96 (d, J¼8.2 Hz, 1H), 7.57 (t,
158.2, 143.2, 137.7, 128.7, 126.8, 126.2, 37.2, 28.0, 26.7, 22.7;
C14H14O2: calcd C 78.48, H 6.59; found C 78.60, H 6.68.
J¼7.6 Hz, 1H), 7.46 (t, J¼7.6 Hz, 1H), 7.28 (d, J¼8.2 Hz, 1H), 6.11 (s,
1H), 3.85 (s, 3H), 2.94 (m, 2H), 2.59 (m, 2H); 13C NMR (50 MHz,
CDCl3)
d 209.3, 178.4, 167.1, 138.2, 132.1, 131.0, 130.4, 129.0, 128.6,
3.21. 3-(4-Propionylphenyl)-cyclohex-2-enone (19)
127.9, 52.4, 35.8, 32.6; C13H12O3: calcd C 72.21, H 5.59; found C
72.36, H 5.38.
From 4-bromopropiophenone (0.213 g, 1 mmol) and cyclohex-
2-en-1-one, product 19 was obtained in 57% (0.130 g) yield.
3.15. 3-(Naphthalen-1-yl)-cyclopent-2-enone (13)
1H NMR (200 MHz, CDCl3)
d
7.98 (d, J¼8.4 Hz, 2H), 7.59 (d,
J¼8.4 Hz, 2H), 6.43 (s, 1H), 3.02 (q, J¼7.6 Hz, 2H), 2.77 (t, J¼7.6 Hz,
From 1-bromonaphthalene (0.207 g, 1 mmol) and cyclopent-2-
2H), 2.49 (t, J¼7.6 Hz, 2H), 2.19 (m, 2H), 1.22 (t, J¼7.6 Hz, 3H); 13C
en-1-one, product 13 was obtained in 77% (0.160 g) yield.
NMR (50 MHz, CDCl3) d 200.0,199.6,158.3,142.9,137.5, 128.3, 126.6,
1H NMR (200 MHz, CDCl3)
d
8.08 (m, 1H), 7.98–7.88 (m, 2H),
7.60–7.40 (m, 4H), 6.50 (s, 1H), 3.12 (m, 2H), 2.66 (m, 2H); 13C NMR
(50 MHz, CDCl3) 209.1,174.9,134.0,133.7,133.4,130.0,129.9,128.6,
126.2, 37.1, 31.9, 28.0, 22.7, 8.1; C15H16O2: calcd C 78.92, H 7.06;
found C 78.71, H 7.14.
d
126.8, 126.2, 124.9, 124.6, 124.4, 35.1, 32.6; C15H12O: calcd C 86.51, H
5.81; found C 86.40, H 5.94.
3.22. 4-(3-Oxocyclohex-1-enyl)-benzaldehyde (20)
From 4-bromobenzaldehyde (0.185 g, 1 mmol) and cyclohex-2-
3.16. 3-(Anthracen-9-yl)-cyclopent-2-enone (14)
en-1-one, product 20 was obtained in 50% (0.100 g) yield.
1H NMR (200 MHz, CDCl3)
d
10.04 (s, 1H), 7.92 (d, J¼8.4 Hz, 2H),
From 9-bromoanthracene (0.257 g, 1 mmol) and cyclopent-2-
en-1-one, product 14 was obtained in 57% (0.147 g) yield.
7.67 (d, J¼8.4 Hz, 2H), 6.45 (s, 1H), 2.82 (t, J¼7.6 Hz, 2H), 2.51 (t,
J¼7.6 Hz, 2H), 2.18 (m, 2H); 13C NMR (50 MHz, CDCl3)
d 199.5, 191.5,

494
Y. Fall et al. / Tetrahedron 65 (2009) 489–495
158.1, 144.6, 136.9, 129.9, 127.2, 126.6, 37.1, 28.1, 22.7; C13H12O2:
calcd C 77.98, H 6.04; found C 77.79, H 6.00.
3.30. 3-(Naphthalen-1-yl)-cyclohex-2-enone (28)
From 1-bromonaphthalene (0.207 g, 1 mmol) and cyclohex-2-
en-1-one, product 28 was obtained in 51% (0.113 g) yield.
3.23. 3-(4-Benzoylphenyl)-cyclohex-2-enone (21)
1H NMR (200 MHz, CDCl3)
d 8.00–7.90 (m, 3H), 7.60–7.40 (m,
3H), 7.32 (d, J¼8.0 Hz, 1H), 6.21 (s, 1H), 2.77 (t, J¼7.6 Hz, 2H), 2.60 (t,
From 4-bromobenzophenone (0.261 g, 1 mmol) and cyclohex-2-
J¼7.6 Hz, 2H), 2.26 (m, 2H).
en-1-one, product 21 was obtained in 53% (0.146 g) yield.
1H NMR (200 MHz, CDCl3)
d 8.00–7.30 (m, 9H), 6.47 (s, 1H), 2.83
(t, J¼7.6 Hz, 2H), 2.51 (t, J¼7.6 Hz, 2H), 2.18 (m, 2H); 13C NMR
3.31. 3-(Pyridin-3-yl)-cyclohex-2-enone (29)
(50 MHz, CDCl3) d 199.5,195.8,158.4,142.5,138.4,137.1,132.6,130.3,
From 3-bromopyridine (0.158 g, 1 mmol) and cyclohex-2-en-1-
129.9, 128.3, 126.7, 125.9, 37.2, 28.0, 22.7; C19H16O2: calcd C 82.58, H
5.84; found C 82.47, H 6.02.
one, product 29 was obtained in 56% (0.098 g) yield.
1H NMR (200 MHz, CDCl3)
7.79 (d, J¼7.7 Hz, 1H), 7.35 (dd, J¼7.7 and 4.0 Hz, 1H), 6.42 (s, 1H),
2.80 (t, J¼7.6 Hz, 2H), 2.54 (t, J¼7.6 Hz, 2H), 2.25 (m, 2H).
d
8.78 (s, 1H), 8.64 (d, J¼4.0 Hz, 1H),
3.24. 4-(3-Oxocyclohex-1-enyl)-benzoic acid methyl ester (22)
From methyl 4-bromobenzoate (0.215 g, 1 mmol) and cyclohex-
3.32. 3-(Quinolin-3-yl)-cyclohex-2-enone (30)
2-en-1-one, product 22 was obtained in 48% (0.111 g) yield.
1H NMR (200 MHz, CDCl3)
d
8.09 (d, J¼8.2 Hz, 2H), 7.58 (d,
From 3-bromoquinoline (0.208 g, 1 mmol) and cyclohex-2-en-
J¼8.2 Hz, 2H), 6.44 (s, 1H), 3.93 (s, 3H), 2.78 (t, J¼7.6 Hz, 2H), 2.50 (t,
J¼7.6 Hz, 2H), 2.20 (m, 2H); 13C NMR (50 MHz, CDCl3)
d 199.6, 166.4,
1-one, product 30 was obtained in 59% (0.132 g) yield.
1H NMR (200 MHz, CDCl3)
d 9.07 (s, 1H), 8.24 (s, 1H), 8.09 (d,
158.4, 143.1, 130.2, 129.9, 126.7, 126.0, 52.3, 37.2, 28.0, 22.7;
C14H14O3: calcd C 73.03, H 6.13; found C 73.14, H 6.00.
J¼8.3 Hz, 1H), 7.84 (d, J¼8.3 Hz, 1H), 7.71 (t, J¼7.7 Hz, 1H), 7.57 (t,
J¼7.7 Hz, 1H), 6.58 (s, 1H), 2.87 (t, J¼7.6 Hz, 2H), 2.54 (t, J¼7.6 Hz,
2H), 2.23 (m, 2H); 13C NMR (50 MHz, CDCl3)
d 199.1, 156.3, 148.3,
3.25. 4-(3-Oxocyclohex-1-enyl)-benzonitrile (23)
147.8, 133.3, 131.2, 130.5, 129.2, 128.3, 127.4, 127.2, 126.4, 37.1, 27.7,
22.6; C15H13NO: calcd C 80.69, H 5.87; found C 80.47, H 5.79.
From 4-bromobenzonitrile (0.182 g, 1 mmol) and cyclohex-2-
en-1-one, product 23 was obtained in 64% (0.126 g) yield.
1H NMR (200 MHz, CDCl3)
d
7.71 (d, J¼8.2 Hz, 2H), 7.60 (d,
3.33. 3-(Isoquinolin-4-yl)-cyclohex-2-enone (31)
J¼8.2 Hz, 2H), 6.41 (s, 1H), 2.78 (t, J¼7.6 Hz, 2H), 2.51 (t, J¼7.6 Hz,
From 4-bromoisoquinoline (0.208 g, 1 mmol) and cyclohex-2-
2H), 2.20 (m, 2H).
en-1-one, product 31 was obtained in 60% (0.134 g) yield.
1H NMR (200 MHz, CDCl3)
d 9.20 (s, 1H), 8.24 (s, 1H), 8.00 (d,
3.26. 3-(3-Oxocyclohex-1-enyl)-benzonitrile (24)
J¼8.3 Hz, 1H), 7.85 (d, J¼8.3 Hz, 1H), 7.67 (t, J¼7.7 Hz, 1H), 7.59 (t,
J¼7.7 Hz, 1H), 6.21 (s, 1H), 2.79 (t, J¼7.6 Hz, 2H), 2.59 (t, J¼7.6 Hz,
From 3-bromobenzonitrile (0.182 g, 1 mmol) and cyclohex-2-
2H), 2.25 (m, 2H); 13C NMR (50 MHz, CDCl3)
d 198.9, 158.5, 153.1,
en-1-one, product 24 was obtained in 51% (0.101 g) yield.
1H NMR (200 MHz, CDCl3)
d 7.95–7.40 (m, 4H), 6.34 (s, 1H), 2.74
143.8, 140.3, 132.4, 132.0, 131.0, 130.5, 128.2, 127.5, 123.7, 37.3, 31.5,
23.1; C15H13NO: calcd C 80.69, H 5.87; found C 80.42, H 5.98.
Registry No.: 7, 111945-91-6; 23, 123732-13-8; 24, 130339-70-7;
25, 77545-60-9; 26, 42160-93-0; 28, 42160-94-1; 29, 63843-14-1.
(t, J¼7.6 Hz, 2H), 2.50 (t, J¼7.6 Hz, 2H), 2.17 (m, 2H).
3.27. 3-(Benzo[1,3]dioxol-5-yl)-cyclohex-2-enone (25)
References and notes
From 4-bromo-1,2-(methylenedioxy)benzene (0.201 g, 1 mmol)
and cyclohex-2-en-1-one, product 25 was obtained in 46% (0.100 g)
yield.
1. For reviews on the Heck reaction see: (a) Beletskaya, I.; Cheprakov, A. Chem. Rev.
2000, 100, 3009; (b) Withcombe, N.; Hii (Mimi), K. K.; Gibson, S. Tetrahedron
2001, 57, 7449; (c) Littke, A.; Fu, G. Angew. Chem., Int. Ed. 2002, 41, 4176; (d)
Farina, V. Adv. Synth. Catal. 2004, 346, 1553.
1H NMR (200 MHz, CDCl3)
d
7.26 (s, 1H), 7.10 (d, J¼8.0 Hz, 1H),
6.83 (d, J¼8.0 Hz,1H), 6.34 (s, 1H), 6.01 (s, 1H), 2.71 (t, J¼7.6 Hz, 2H),
2. For Heck vinylations with linear alk-1-en-3-ones and aryl iodides: (a) Ziegler, F.
E.; Chakraborty, U. R.; Weisenfeld, R. B. Tetrahedron 1981, 37, 4035; (b) Cacchi,
S.; Arcadi, A. J. Org. Chem. 1983, 48, 4236; (c) Jeffery, T. J. Chem. Soc., Chem.
Commun. 1984, 1287; (d) Cacchi, S.; Palmieri, G. Synthesis 1984, 575; (e) Ohff,
M.; Ohff, A.; van der Boom, M. E.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687;
(f) Anson, M. S.; Mirza, A. R.; Tonks, L.; Williams, J. M. J. Tetrahedron Lett. 1999,
40, 7147; (g) Cacchi, S.; Fabrizi, G.; Gasparrini, F.; Villani, C. Synlett 1999, 345;
(h) Hagiwara, H.; Shimizu, Y.; Hoshi, T.; Suzuki, T.; Ando, M.; Ohkubo, K.; Yo-
koyama, C. Tetrahedron Lett. 2001, 42, 4349; (i) Cacchi, S.; Fabrizi, G.; Goggia-
mani, A. Arkivoc 2003, 8, 58; (j) Bianco, A.; Cavarischia, C.; Farina, A.; Guiso, M.;
Marra, C. Tetrahedron Lett. 2003, 44, 9107; (k) Botella, L.; Najera, C. Tetrahedron
Lett. 2004, 45, 1833; (l) Cesati, R. R.; de Armas, J.; Hoveyda, A. H. J. Am. Chem.
Soc. 2004, 126, 96; (m) Yang, D.; Chen, Y.-C.; Zhu, N.-Y. Org. Lett. 2004, 6, 1577;
(n) Gupta, A. K.; Song, C. H.; Oh, C. H. Tetrahedron Lett. 2004, 45, 4113; (o)
Bianco, A.; Cavarischia, C.; Guiso, M. Eur. J. Org. Chem. 2004, 2894; (p) Martinez,
S.; Vallribera, A.; Cotet, C. L.; Popovici, M.; Martin, L.; Roig, A.; Moreno-Manas,
M.; Molins, E. New J. Chem. 2005, 29, 1342; (q) Arisawa, M.; Hamada, M.; Ta-
kamiya, I.; Shimoda, M.; Tsukamoto, S.; Arakawa, Y.; Nishida, A. Adv. Synth.
Catal. 2006, 348, 1063; (r) Alacid, E.; Najera, C. Synlett 2006, 2959; (s) Arcadi, A.;
Attanasi, O. A.; Berretta, S.; Bianchi, G.; Filippone, P. Synthesis 2006, 2523; (t)
Climent, M. J.; Corma, A.; Iborra, S.; Mifsud, M. Adv. Synth. Catal. 2007, 349, 1949.
3. For Heck vinylations with linear alk-1-en-3-ones and aryl bromides: (a) Aslam,
M.; Elango, V.; Davenport, K. G. Synthesis 1989, 869; (b) Semmelhack, M. F.; Ho,
S.; Cohen, D.; Streigerwald, M.; Lee, M. C.; Lee, G.; Gilbert, A. M.; Wulff, W. D.;
Ball, R. G. J. Am. Chem. Soc. 1994, 116, 7108; (c) Hagiwara, H.; Eda, Y.; Morohashi,
K.; Suzuki, T.; Ando, M.; Ito, N. Tetrahedron Lett. 1998, 39, 4055; (d) Uchiro, H.;
Nagasawa, K.; Aiba, Y.; Kobayashi, S. Tetrahedron Lett. 2000, 41, 4165; (e) Uchiro,
2.48 (t, J¼7.6 Hz, 2H), 2.14 (m, 2H).
3.28. 3-(Naphthalen-2-yl)-cyclohex-2-enone (26)
From 2-bromonaphthalene (0.207 g, 1 mmol) and cyclohex-2-
en-1-one, product 26 was obtained in 55% (0.122 g) yield.
1H NMR (200 MHz, CDCl3)
d 8.10 (s, 1H), 7.95–7.85 (m, 3H), 7.60
(d, J¼8.0 Hz, 1H), 7.60–7.40 (m, 2H), 6.57 (s, 1H), 2.90 (t, J¼7.6 Hz,
2H), 2.53 (t, J¼7.6 Hz, 2H), 2.20 (m, 2H).
3.29. 2-(3-Oxocyclohex-1-enyl)-benzonitrile (27)
From 2-bromobenzonitrile (0.182 g, 1 mmol) and cyclohex-2-
en-1-one, product 27 was obtained in 39% (0.077 g) yield.
1H NMR (200 MHz, CDCl3)
d
7.73 (d, J¼8.2 Hz, 1H), 7.64 (t,
J¼7.6 Hz, 1H), 7.51 (t, J¼7.6 Hz, 1H), 7.38 (d, J¼8.2 Hz, 1H), 6.20 (s,
1H), 2.82 (t, J¼7.6 Hz, 2H), 2.54 (t, J¼7.6 Hz, 2H), 2.21 (m, 2H); 13C
NMR (50 MHz, CDCl3) d 198.8, 158.5, 144.3, 133.7, 133.0, 129.8, 129.0,
127.9, 117.7, 110.0, 37.2, 30.1, 23.1; C13H11NO: calcd C 79.16, H 5.62;
found C 79.07, H 5.45.

Y. Fall et al. / Tetrahedron 65 (2009) 489–495
495
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4. Lemhadri, M.; Doucet, H.; Santelli, M. Synlett 2006, 2935.
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M.; Reisman, S. E.; Hirata, M.; Weiss, M. M.; Tamaki, K.; Ovasaka, T. V.; Wood,
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12. (a) Feuerstein, M.; Doucet, H.; Santelli, M. J. Org. Chem. 2001, 66, 5923; (b)
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13. Lemhadri, M.; Battace, A.; Berthiol, F.; Zair, T.; Doucet, H.; Santelli, M. Synthesis
2008, 1142.