A novel stereoselective synthesis of symmetrical (1E,3E)-1,4-diarylbuta-1, 3-dienes

Article abstract of DOI:10.1055/s-2007-983833

A convenient methodology for the stereoselective synthesis of symmetrical (1E,3E)-1,4-diarylbuta-1,3-dienes based on palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of (1E,3E)-1,4-diiodobuta-1,3-diene with arylboronic reagents is reported. Georg Thieme Verlag Stuttgart.

Full text of DOI:10.1055/s-2007-983833

3
088
PRACTICAL SYNTHETIC PROCEDURES
A Novel Stereoselective Synthesis of Symmetrical
(
1E,3E)-1,4-Diarylbuta-1,3-dienes
o Babudri,a,b Gianluca M. Farinola,* Francesco Naso, Roberta Ragni, Giulia Spinaa
a
a,b
a
A
F
Novel Stere
r
oselectiv
a
e
Synthesis
n
of Symmetr
c
ical (1
E
,3
E
e
)-1,4-Diar
y
s
lbuta-1,3-
c
diene
s
a
Dipartimento di Chimica, Università degli Studi di Bari, via Orabona 4, 70126 Bari, Italy
Fax +39(80)5442129; E-mail: farinola@chimica.uniba.it
b
CNR ICCOM Bari, Dipartimento di Chimica, Università degli Studi di Bari, via Orabona 4,
PSP
7
0126 Bari, Italy
Received 8 March 2007; revised 26 March 2007
No97
Abstract: A convenient methodology for the stereoselective synthesis of symmetrical (1E,3E)-1,4-diarylbuta-1,3-dienes based on palladi-
um-catalyzed Suzuki–Miyaura cross-coupling reaction of (1E,3E)-1,4-diiodobuta-1,3-diene with arylboronic reagents is reported.
Key words: diene, Suzuki cross-coupling reaction, stereoselective synthesis, palladium
O
O
Pd(PPh3)4, Ag2O
I
Ar
+
Ar B(OH)2 or Ar
B
I
Ar
THF, H2O
r.t.
1
2a–h
3a–h
Scheme 1
Introduction
aration of unsymmetrically functionalized buta-1,3-
dienes have also been developed based on cross-coupling
The synthesis of stereodefined conjugated dienes is a top- reactions of vinyl halides or triflates with alkenyl-substi-
1
5
ic of considerable interest because this structural motif is tuted organometallic compounds such as vinylboron,
frequently met in biologically active compounds such as, -tin,16 -zinc, -germanium, -zirconium, or -magne-
for example, pheromones, and in organic materials used sium derivatives. In many cases these homocoupling
as fluorescent probes, dopant emitters in electrolumines- and cross-coupling processes are highly stereoselective.
17
18
19
1
20
2
3
4
cent devices, or nonlinear optical chromophores. More-
over, these molecules are useful substrates in various
reactions, the most common being Diels–Alder cycliza-
High stereoselectivity has been also achieved in synthetic
methods involving coupling reactions of preformed di-
enyl moieties bearing nucleophilic or electrophilic reac-
tive sites.
5
tions.
Several synthetic routes to functionalized conjugated
dienes have been developed. Among them, methodolo-
Examples involving nucleophilic dienyl building blocks
are represented by the cross-coupling of aryl halides with
mono- or bis-metalated buta-1,3-dienyl reagents such as
6
gies based on the Wittig alkenation of aldehydes, the re-
arrangement of cyclopropylcarbinyl derivatives,7
21
22
2
-aryl-3-silyl-, 1,4-bis-silyl-, or 1-boryl-4-stannylbu-
8
intermolecular enyne metathesis, and anil synthesis with
23
ta-1,3-dienes. 1,4-Bis-silylated dienes have also been
used in acylation reactions with carboxylic acid chloride–
aluminum trichloride complexes.
9
Schiff bases and propenyl substrates have found various
applications. However, many of these strategies suffer
from poor stereocontrol on formation of the conjugated
double bonds.
24
The complementary approach based on cross-coupling re-
actions of organometallic reagents with bis-electrophilic
buta-1,3-dienes has not been extensively investigated,
with the exception of a few examples including cross-cou-
pling processes of Grignard reagents with 2,3-dichlorobu-
Alternative synthetic approaches involve transition-met-
1
0
al-catalyzed coupling reactions of vinyl organometallic
compounds and/or alkenyl electrophiles. The homocou-
1
1
12
pling of alkenylstannanes, vinylboronic acids or unsat-
25
26
ta-1,3-diene,
(1E,3E)-1,4-diiodobuta-1,3-diene (1),
1
3
urated silanes, as well as the metal-promoted reductive
27
and (1E,3E)-1-bromo-4-(phenylthio)buta-1,3-diene, the
latter two proceed with complete retention of double bond
configuration.
1
4
dimerization of vinyl halides have been used as synthet-
ic tools for the synthesis of symmetrically functionalized
buta-1,3-dienes. A number of methodologies for the prep-
SYNTHESIS 2007, No. 19, pp 3088–3092
x
x.
x
x
.
2
0
0
7
Advanced online publication: 30.07.2007
DOI: 10.1055/s-2007-983833; Art ID: Z06007SS
Georg Thieme Verlag Stuttgart · New York
©

PRACTICAL SYNTHETIC PROCEDURES
Scope and Limitations
Symmetrical (1E,3E)-1,4-Diarylbuta-1,3-dienes
3089
Beletskaya et al.,29 diiodobutadiene 1 can be easily pre-
pared by dimerization of acetylene accompanied by addi-
In the framework of our studies on the stereoselective syn- tion of iodine in the presence of a platinum(IV) catalyst
2
8
thesis of polyconjugated organic compounds, we have and sodium iodide (Scheme 2) and it can be isolated by
developed a convenient protocol for the preparation of all- crystallization (H O–MeOH).
2
E symmetrical 1,4-diarylbuta-1,3-dienes that is based on
the palladium-catalyzed Suzuki–Miyaura cross-coupling
reaction of aromatic boronic derivatives with (1E,3E)-
NaI, Na2PtCl6⋅H2O
I
H
H
+
I2
I
MeOH
1
1
,4-diiodobuta-1,3-diene (1) (Scheme 1). As reported by
Scheme 2 Synthesis of (1E,3E)-1,4-diiodobuta-1,3-diene
Table 1 Suzuki–Miyaura Cross-Coupling Reaction between the (1E,3E)-1,4-Diiodobuta-1,3-diene (1) and Boronic Reagents
a
Entry
Boronic reagent
Diene
Yield (%)
1
B(OH)2
95
80
45
2
a
3
3
a
2
3
B(OH)2
B(OH)2
2
b
b
F3C
F3C
CF3
2
c
3
c
4
67
B(OH)2
2
d
3
d
F3CO
5
6
7
F3CO
B(OH)2
84
90
86
OCF3
2
e
3
e
B(OH)2
S
S
S
2
f
3
f
B(OH)2
O
O
O
2
g
3
g
O
S
B
S
S
S
8
87
S
O
S
2
h
3
h
a
Yields refer to pure isolated products.
Synthesis 2007, No. 19, 3088–3092 © Thieme Stuttgart · New York

3
090
F. Babudri et al.
PRACTICAL SYNTHETIC PROCEDURES
The simple synthesis of 1 made it particularly attractive in starts from easily available reagents and that can be also
our search for an electrophilic butadienyl building block used for the synthesis of extended conjugated systems.
for cross-coupling reactions with organometallic re-
agents, especially if compared with the corresponding
Arylboronic reagents 2a–h, Pd(PPh ) , and Ag O (Lancaster and
Aldrich) were used without further purification. THF was distilled
3
4
2
3
0
chloro derivative (1E,3E)-1,4-dichlorobuta-1,3-diene or
31
with the all-Z counterparts (1Z,3Z)-1,4-diiodo- and from Na/benzophenone under N immediately prior to use. H O–
2
2
3
2
(
1Z,3Z)-1,4-dibromobuta-1,3-diene, whose syntheses THF mixture used as the reaction solvent was carefully degassed by
bubbling N . The diiodobutadiene 1 was prepared according to the
appear complicated.
2
2
9
literature and it was stored at 4 °C. Column chromatography was
performed using silica gel 60, 40–63 mm from Merck. FT-IR spectra
were measured on a Perkin Elmer Spectrum BX spectrophotometer.
Although one example of the cross-coupling of butadiene
1
with phenylmagnesium bromide was described by Be-
2
6
1
13
letskaya et al., we preferred to investigate the Suzuki–
H NMR and C NMR spectra were recorded in CDCl on a Bruker
3
Miyaura reaction, which appears more convenient, both in AM 500 spectrometer. For peak multiplicity, standard abbrevia-
tions are used; in addition, ‘d like’ is used to describe pattern which
terms of organometallic substrate availability and experi-
rigorously cannot be a doublet but experimentally appear like broad
doublets because of the presence of longe-range low coupling con-
stants. MS spectra were recorded on a Polaris Q Thermo Electron
mental conditions, as a general approach to convert ste-
reoselectively 1 into diaryl-functionalized butadienes.
To check both scope and limitations of the methodology Corporation spectrometer. Elemental analyses were performed on a
Carlo Erba CHNS-O EA1108-Elemental Analyzer.
proposed, 1 was coupled with commercially available
arylboronic acids 2a–g (Scheme 1). The coupling reac-
(
1E,3E)-1,4-Diarylbuta-1,3-dienes 3a–h; General Procedure
tions were performed in tetrahydrofuran/water using tet-
rakis(triphenylphosphine)palladium(0) [Pd(PPh ) ] as the
A mixture of (1E,3E)-1,4-diiodobuta-1,3-diene (1, 306 mg, 1
mmol), arylboronic acid 2a–g or ester 2h (2.5 mmol), catalyst
3
4
catalyst, in the presence of silver oxide as the base, and at Pd(PPh ) (23 mg, 0.02 mmol), and Ag O (695 mg, 3 mmol) in THF
3
4
2
room temperature. Due to the mild experimental condi- (12 mL) and H O (3 mL) was stirred at r.t. for 12 h. The mixture was
2
subsequently filtered to remove Ag O. The organic soln was ex-
tions, the process tolerates the presence of various substit-
uents in the arylboronic acid reagent, affording
functionalized 1,4-diarylbuta-1,3-dienes (Table 1) in
good to excellent yields, with the exception of the arylbo-
ronic acid 2c, functionalized with the strongly electron-
withdrawing trifluoromethyl group (entry 3), which gave spectively).
diene 3c in only 45% yield. The coupling reaction appears
2
tracted with hexane (3 × 15 mL) [CH Cl (3 × 25 mL) was used for
2
2
3
h] and the organic extracts were dried (anhyd Na SO ). After dis-
2 4
tillation of the solvent at reduced pressure, the crude product was
purified by column chromatography (silica gel, petroleum ether or,
in the case of 3d and 3h, petroleum ether–CH Cl , 9.5:0.5 or 8:2, re-
2
2
(
1E,3E)-1,4-Diphenylbuta-1,3-diene (3a)9a
Pale yellow solid; yield: 196 mg (95%); mp 149–150 °C (Lit. 150–
53 °C).
to be slightly sensitive to sterical hindrance by the methyl
group ortho to the boronic functionality in 2d, as shown
by the decrease in yield to 67% (entry 4). The process is
also very efficient with heteroarylboronic acids, such as
thienyl and furyl reagents (entries 6 and 7). A boronic es-
9
a
1
–
1
IR (KBr): 3015, 1491, 1444, 1269, 990, 740, 690 cm .
1
H NMR (500 MHz, CDCl ): d = 6.64–6.73 (m, 2 H), 6.93–7.01 (m,
3
ter can be used in place of the corresponding acid, as in the 2 H), 7.21–7.27 (m, 2 H), 7.31–7.37 (m, 4 H), 7.43–7.47 (m, 4 H).
1
3
case of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
,2¢-bithiophene (2h) (Scheme 1 and Table 1, entry 8). 132.77, 137.28.
This example also shows the versatility of our approach
C NMR (125 MHz, CDCl ): d = 126.34, 127.52, 128.61, 129.19,
3
2
+
GC-MS (EI, 70 eV): m/z (%) = 206 (100) [M] , 205 (44), 191 (46),
for the synthesis of extended conjugated systems of poten- 129 (13), 128 (36), 91 (44).
tial interest as organic molecular semiconductors and ma-
terials for nonlinear optics.
Anal. Calcd for C H : C, 93.16; H, 6.84. Found: C, 93.25; H, 6.90.
1
6
14
(
1E,3E)-1,4-Bis(4-isopropylphenyl)buta-1,3-diene (3b)
The stereochemistry of dienes 3a–h can not be directly
derived from the H NMR spectra on the basis of the cou-
pling constants of the protons of the diene moiety, because
they appear as a second order AA¢BB¢ spin system. How-
ever, the analysis of this spin system by means of
MestReC NMR software allowed us to define the cou-
Pale yellow solid; yield: 232 mg (80%); mp 139–141 °C.
1
–
1
IR (KBr): 3015, 2957, 1509, 1456, 992, 853, 805 cm .
1
H NMR (500 MHz, CDCl ): d = 1.26 (d, J = 6.9 Hz, 12 H), 2.90
3
(
sept., J = 6.9 Hz, 2 H), 6.58–6.69 (m, 2 H), 6.86–6.96 (m, 2 H),
7
.20 (d, J = 8.1 Hz, 4 H), 7.37 (d, J = 8.1 Hz, 4 H).
): d = 23.90, 33.87, 126.30, 126.69,
28.61, 132.22, 135.08, 148.32.
GC-MS (EI, 70 eV): m/z (%) = 290 (29) [M] , 247 (32), 205 (100).
pling constant values J(AB) = J(A¢B¢) ~ 16 Hz, J(BB¢) 13C NMR (125 MHz, CDCl
3
1
=
9–11 Hz, J(AB¢) = 0–2 Hz, J(AA¢) ~ 0 Hz for 3a–h,
+
which are characteristic of a (1E,3E)-diene structure.
Therefore, the spectral analysis shows that the reaction Anal. Calcd for C22
proceeds with complete retention of configuration of the
H26: C, 90.98; H, 9.02. Found: C, 90.85; H, 8.93.
(
1E,3E)-1,4-Bis[4-(trifluoromethyl)phenyl]buta-1,3-diene (3c)
1
,3-dienyl moiety of 1, thus leading only to stereodefined
Pale yellow solid; yield: 154 mg (45%); mp 145–147 °C.
(
1E,3E)-1,4-diarylbuta-1,3-dienes.
IR (KBr): 1612, 1413, 1321, 1179, 1127, 1109, 1066, 1012, 989,
In summary, a simple highly stereoselective route to all-E
symmetrical 1,4-diaryl dienes has been described that
–1
8
62, 807 cm .
1
H NMR (500 MHz, CDCl ): d = 6.71–6.79 (m, 2 H), 6.99–7.08 (m,
3
2
H), 7.54 (d, J = 8.3 Hz, 4 H), 7.60 (d, J = 8.3 Hz, 4 H).
Synthesis 2007, No. 19, 3088–3092 © Thieme Stuttgart · New York

PRACTICAL SYNTHETIC PROCEDURES
Symmetrical (1E,3E)-1,4-Diarylbuta-1,3-dienes
3091
1
3
1
C NMR (125 MHz, CDCl ): d = 124.13 (q, J = 271.7 Hz),
Anal. Calcd for C H O : C, 77.40; H, 5.41. Found: C, 77.51; H,
5.49.
3
C-F
2
12 10
2
3
1
1
25.63 (q, J = 3.7 Hz), 126.56, 129.45 (q, J = 32.4 Hz),
30.92, 132.66, 140.37.
C-F
C-F
+
(1E,3E)-1,4-Bis(2,2¢-bithiophen-5-yl)buta-1,3-diene (3h)
Red solid; yield: 333 mg (87%); mp 210–212 °C.
GC-MS (EI, 70 eV): m/z (%) = 342 (58) [M] , 323 (12), 273 (100),
33 (78), 204 (18), 159 (24).
2
IR(KBr): 3100, 3062, 3006, 1600, 1496, 1425, 1233, 1055, 970,
Anal. Calcd for C H F : C, 63.16; H, 3.53. Found: C, 63.22; H,
18
12
6
–1
9
59, 837, 815, 785, 693 cm .
3
.57.
1
H NMR (500 MHz, CDCl ): d = 6.71–6.80 (m, 2 H), 6.86–6.95 (m,
3
(
1E,3E)-1,4-Bis(2,3-dimethylphenyl)buta-1,3-diene (3d)
2 H), 7.06–7.14 (m, 4 H), 7.24 (d, J = 3.7 Hz, 2 H), 7.33 (d, J = 3.5
Hz, 2 H), 7.53 (d, J = 5.0 Hz, 2 H).
Yellow solid; yield: 176 mg (67%); mp 180–182 °C.
1
3
IR(KBr): 3030, 2921, 1574, 1456, 1380, 1262, 1091, 988, 773, 734,
C NMR (125 MHz, CDCl ): d = 124.15, 124.73, 125.41, 125.68,
3
–1
7
07 cm .
127.94, 128.45, 128.57, 135.42, 136.36, 141.20.
1
H NMR (500 MHz, CDCl ): d = 2.31 (s, 6 H), 2.32 (s, 6 H), 6.83–
Anal. Calcd for C H S : C, 62.79; H, 3.69; S, 33.53. Found: C,
62.90; H, 3.77; S, 33.62.
3
20 14 4
6
.92 (m, 2 H), 6.93–7.02 (m, 2 H), 7.05–7.15 (m, 4 H), 7.42 (d like,
J = ~7 Hz, 2 H).
1
3
C NMR (125 MHz, CDCl ): d = 15.30, 20.73, 123.36, 125.51,
3
Acknowledgment
1
29.13, 130.97, 131.13, 134.13, 136.52, 136.88.
+
This work was financially supported by Ministero dell’Istruzione,
dell’Università e della Ricerca (MIUR), ‘Progetto FIRB 2003
SYNERGY RBNE 03S7XZ’ and by Università degli Studi di Bari.
GC-MS (EI, 70 eV): m/z (%) = 262 (25) [M] , 247 (100), 232 (48),
2
17 (18), 119 (10).
Anal. Calcd for C H : C, 91.55; H, 8.45. Found: C, 91.67; H, 8.53.
20
22
(
(
1E,3E)-1,4-Bis[4-(trifluoromethoxy)phenyl]buta-1,3-diene
3e)
References
(
1) Mori, K. The Synthesis of Insect Pheromones, In The Total
Synthesis of Natural Products, Vol. 4; ApSimon, J., Ed.;
John Wiley and Sons: New York, 1981.
Pale orange solid; yield: 314 mg (84%); mp 97–99 °C.
–
1
IR(KBr): 3013, 1600, 1506, 1274, 1222, 1166, 988, 857 cm .
1
H NMR (500 MHz, CDCl ): d = 6.63–6.70 (m, 2 H), 6.87–6.94 (m,
(2) Singh, A. K.; Darshi, M.; Kanvah, S. J. Phys. Chem. A 2000,
3
2
H), 7.19 (d like, J = ~8 Hz, 4 H), 7.45 (d like, J = ~8 Hz, 4 H).
104, 464.
(
(
3) Adachi, C.; Tsutsui, T.; Saito, S. Appl. Phys. Lett. 1990, 56,
99.
4) (a) Kanis, D. R.; Ratner, M. A.; Marks, T. J. Chem. Rev.
994, 94, 195. (b) Mladenova, M.; Ventelon, L.; Blanchard-
1
3
1
C NMR (125 MHz, CDCl ): d = 120.46 (q, J = 257.3 Hz),
3
C-F
3
7
1
21.19, 127.58, 129.70, 131.78, 135.89, 148.50 (q, J = 1.9 Hz).
C-F
+
GC-MS (EI, 70 eV): m/z (%) = 374 (100) [M] , 289 (99), 249 (63),
2
1
03 (44), 202 (40), 175 (24).
Desche, M. Tetrahedron Lett. 1999, 40, 6923.
5) Fringuelli, F.; Taticchi, A. Dienes in the Diels–Alder
Reaction; John Wiley and Sons: New York, 1990.
6) (a) Okukado, N.; Uchikawa, O.; Nakamura, Y. Chem. Lett.
1988, 1449. (b) Ideses, R.; Shani, A. Tetrahedron 1989, 45,
3523. (c) Benahmed-Gasmi, A.; Frère, P.; Elandaloussi, E.
H.; Roncali, J.; Orduna, J.; Garin, J.; Jubault, M.; Riou, A.;
Gorgues, A. Chem. Mater. 1996, 8, 2291. (d) Frère, P.;
Raimundo, J. M.; Blanchard, P.; Delaunay, J.; Richomme,
P.; Sauvajol, J. L.; Orduna, J.; Garin, J.; Roncali, J. J. Org.
Chem. 2003, 68, 7254.
(
(
Anal. Calcd for C H F O : C, 57.76; H, 3.23. Found: C, 57.60; H,
3
18
12
6
2
.11.
1E,3E)-1,4-Bis(2-thienyl)buta-1,3-diene (3f)6c
(
6
c
Pale yellow solid; yield: 197 mg (90%); mp 170–171 °C (Lit. 170
C).
°
IR(KBr): 3098, 1599, 1506, 1421, 1252, 980, 858, 841, 801, 698
cm .
–
1
1
H NMR (500 MHz, CDCl ): d = 6.65–6.73 (m, 2 H), 6.73–6.81 (m,
3
2
1
H), 6.94–7.02 (m, 4 H), 7.18 (d like, J = ~5 Hz, 2 H).
(7) (a) Patro, B.; Ila, H.; Junjappa, H. Tetrahedron Lett. 1992,
33, 809. (b) Yu, C. C.; Ng, D. K. P.; Chen, B.-L.; Luh, T.-Y.
Organometallics 1994, 13, 1487. (c) Ranu, B. C.; Banerjee,
S. Eur. J. Org. Chem. 2006, 3012.
3
C NMR (125 MHz, CDCl ): d = 124.43, 125.40, 125.91, 127.66,
3
1
28.47, 142.84.
+
GC-MS (EI, 70 eV): m/z (%) = 218 (100) [M] , 217 (53), 185 (42),
1
(
8) (a) Diver, S. T.; Giessert, A. J. Synthesis 2003, 466.
84 (67), 152 (12), 134 (9).
(
b) Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317.
(
9) (a) Paventi, M.; Hay, A. S. Synthesis 1990, 878. (b) Wang,
S. J.; Tjong, S. C.; Meng, Y. Z.; Fung, M. K.; Lee, S. T.;
Hay, A. S. J. Appl. Polym. Sci. 2003, 89, 1645.
Anal. Calcd for C H S : C, 66.01; H, 4.62; S, 29.37. Found: C,
1
2
10 2
6
5.88; H, 4.54; S, 29.29.
1E,3E)-1,4-Bis(2-furyl)buta-1,3-diene (3g)6c
Pale yellow solid; yield: 160 mg (86%); mp 90 °C (Lit. 95 °C).
(10) Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de
(
6
c
Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim,
2004.
IR(KBr): 3129, 1463, 1256, 1149, 1014, 988, 922, 883, 791, 736
(
11) (a) Kanemoto, S.; Matsubara, S.; Oshima, K.; Utimoto, K.;
Nozaki, H. Chem. Lett. 1987, 5. (b) Kang, S.-K.;
–
1
cm .
1
H NMR (500 MHz, CDCl ): d = 6.29 (d, J = 3.3 Hz, 2 H), 6.40 (dd,
Namkoong, E.-Y.; Yamaguchi, T. Synth. Commun. 1997,
27, 641. (c) Alcaraz, L.; Taylor, R. J. K. Synlett 1997, 791.
3
J = 3.3, 1.8 Hz, 2 H), 6.40–6.48 (m, 2 H), 6.75–6.83 (m, 2 H), 7.38
(
d, J = 1.8 Hz, 2 H).
(12) (a) Ramana Rao, V. V.; Vijaya Kumar, Ch.;
1
3
Devaprabhakara, D. J. Organomet. Chem. 1979, 179, C7.
C NMR (125 MHz, CDCl ): d = 108.57, 111.74, 120.17, 127.37,
3
(
b) Parrish, J. P.; Jung, Y. C.; Floyd, R. J.; Woon Jung, K.
1
42.19, 153.26.
Tetrahedron Lett. 2002, 43, 7899. (c) Kabalka, G. W.;
Wang, L. Tetrahedron Lett. 2002, 43, 3067.
+
GC/MS (EI, 70 eV): m/z (%) = 186 (100) [M] , 157 (46), 129 (39),
28 (47).
1
Synthesis 2007, No. 19, 3088–3092 © Thieme Stuttgart · New York

3
092
F. Babudri et al.
PRACTICAL SYNTHETIC PROCEDURES
(
13) (a) Tamao, K.; Matsumoto, H.; Kakui, T.; Kumada, M.
(23) Coleman, R. S.; Walczak, M. C. Org. Lett. 2005, 7, 2289.
(24) (a) Babudri, F.; Fiandanese, V.; Naso, F. J. Org. Chem.
1991, 56, 6245. (b) Babudri, F.; Cicciomessere, A. R.;
Farinola, G. M.; Fiandanese, V.; Marchese, G.; Musio, R.;
Naso, F.; Sciacovelli, O. J. Org. Chem. 1997, 62, 3291.
(25) Yamamoto, T.; Yasuda, T.; Kobayashi, K.; Yamaguchi, I.;
Koizumi, T.-a.; Ishii, D.; Nakagawa, M.; Mashiko, Y.;
Shimizu, N. Bull. Chem. Soc. Jpn. 2006, 79, 498.
(26) Trostyanskaya, I. G.; Titskiy, D. Y.; Anufrieva, E. A.;
Borisenko, A. A.; Kazankova, M. A.; Beletskaya, I. P. Russ.
Chem. Bull., Int. Ed. 2001, 50, 2095.
Tetrahedron Lett. 1979, 20, 1137. (b) Itami, K.; Ushiogi,
Y.; Nokami, T.; Ohashi, Y.; Yoshida, J.-i. Org. Lett. 2004, 6,
3695.
(
(
14) (a) Tanaka, H.; Kosaka, A.; Yamashita, S.; Morisaki, K.;
Torii, S. Tetrahedron Lett. 1989, 30, 1261. (b) Lee, P. H.;
Seomoon, D.; Lee, K. Org. Lett. 2005, 7, 343.
15) (a) Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. J.
Am. Chem. Soc. 1985, 107, 972. (b) Kobayashi, Y.;
William, A. D. Org. Lett. 2002, 4, 4241. (c) Takagi, J.;
Takahashi, K.; Ishiyama, T.; Miyaura, N. J. Am. Chem. Soc.
2
002, 124, 8001. (d) Molander, G. A.; Felix, L. A. J. Org.
Chem. 2005, 70, 3950. (e) Suzuki, A. Chem. Commun.
005, 4759. (f) Alami, M.; Peyrat, J.-F.; Brion, J.-D.
(27) Babudri, F.; Fiandanese, V.; Mazzone, L.; Naso, F.
Tetrahedron Lett. 1994, 35, 8847.
(28) For some recent reviews see: (a) Babudri, F.; Farinola, G.
M.; Naso, F. J. Mater. Chem. 2004, 14, 11. (b) Babudri, F.;
Farinola, G. M.; Naso, F.; Ragni, R. Chem. Commun. 2007,
1003.
(29) (a) Mitchenko, S. A.; Ananikov, V. P.; Beletskaya, I. P.;
Ustynyuk, Y. A. Mendeleev Commun. 1997, 130.
(b) Mitchenko, S. A. Kinet. Catal. 1999, 40, 253.
(c) Ananikov, V. P.; Musaev, D. G.; Morokuma, K.
Organometallics 2001, 20, 1652. (d) Ananikov, V. P.;
Mitchenko, S. A.; Beletskaya, I. P. Russ. J. Org. Chem.
(Engl. Transl.) 2002, 38, 636.
2
Tetrahedron Lett. 2002, 43, 3007.
(
(
16) Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813.
17) (a) Tucker, C. E.; Majid, T. N.; Knochel, P. J. Am. Chem.
Soc. 1992, 114, 3983. (b) Zeng, X.; Qian, M.; Hu, Q.;
Negishi, E.-i. Angew. Chem. Int. Ed. 2004, 43, 2259.
18) Wang, Z.; Wnuk, S. F. J. Org. Chem. 2005, 70, 3281.
19) (a) Cai, M.; Ye, H.; Zhao, H.; Song, C. J. Organomet. Chem.
(
(
2003, 687, 462. (b) Cai, M.-Z.; Ye, X.-L.; Wang, P.-P.
Synthesis 2005, 2654.
(
(
(
20) Fiandanese, V.; Marchese, G.; Mascolo, G.; Naso, F.;
Ronzini, L. Tetrahedron Lett. 1988, 29, 3705.
21) Ikeda, Z.; Oshima, K.; Matsubara, S. Org. Lett. 2005, 7,
(30) Kielh, A.; Eberhardt, A.; Müllen, K. Liebigs Ann. Chem.
1995, 223.
4
859.
(31) Ashe, A. J. III.; Drone, F. J. Organometallics 1985, 4, 1478.
(32) Ferede, R.; Noble, M.; Cordes, A. W.; Allison, N. T.; Lay, J.
Jr. J. Organomet. Chem. 1988, 339, 1.
22) (a) Babudri, F.; Farinola, G. M.; Fiandanese, V.; Mazzone,
L.; Naso, F. Tetrahedron 1998, 54, 1085. (b) Denmark, S.
E.; Tymonko, S. A. J. Am. Chem. Soc. 2005, 127, 8004.
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