Lewis acid InBr3-catalyzed arylation of diorgano diselenides and ditellurides with arylboronic acids

Article abstract of DOI:10.1039/b914533h

A novel Lewis acid InBr₃-catalyzed direct cross-coupling reaction of arylboronic acids with diorgano diselenides and ditellurides without any additive has been developed. The reactions generated the corresponding unsymmetrical diorgano monoselenides and monotellurides in good to excellent yields. The method has advantages of broad substrate scope, simple operation, mild reaction conditions and high effectiveness. A possible reaction mechanism was proposed. The Royal Society of Chemistry 2009.

Full text of DOI:10.1039/b914533h

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www.rsc.org/obc | Organic & Biomolecular Chemistry
Lewis acid InBr3-catalyzed arylation of diorgano diselenides and ditellurides
with arylboronic acids†
Kai Ren,a Min Wanga and Lei Wang*a,b
Received 20th July 2009, Accepted 18th August 2009
First published as an Advance Article on the web 23rd September 2009
DOI: 10.1039/b914533h
A novel Lewis acid InBr3-catalyzed direct cross-coupling reaction of arylboronic acids with diorgano
diselenides and ditellurides without any additive has been developed. The reactions generated the
corresponding unsymmetrical diorgano monoselenides and monotellurides in good to excellent yields.
The method has advantages of broad substrate scope, simple operation, mild reaction conditions and
high effectiveness. A possible reaction mechanism was proposed.
and stereoselectivity. Compared to conventional Lewis acids,
Introduction
they have advantages of water stability, recyclability, operational
Organic chalcogens, especially with selenium and tellurium as
simplicity, strong tolerance to oxygen and nitrogen-containing
reaction substrates and functional groups.13 As green Lewis acid
catalysts, In(III) salts used in the Diels–Alder,14 Friedel–Crafts,15
Mukaiyama aldol,16 and Sakurai–Hosomi allylation reactions17
have been extensively investigated.18 However, In(III)-catalyzed
preparation of unsymmetrical organochalcogenides has not so far
been described, despite the fact that a reaction of dichalcogenides
with alkyl and acyl halides using a stoichiometric indium(I) iodide
has been reported.19
Organoboronic acids are widely used as reagents in organic
synthesis because they are commercially available, stable, generally
nontoxic, and compatible with a variety of functional groups.
Recently, a copper-catalyzed C–Se and C–Te coupling reaction
of arylboronic acids with diselenides and ditellurides has been
demonstrated by our group.20 After that, synthesis of unsymmetri-
cal monochalcogenides, including sulfides, selenides and tellurides
from dichalcogenides with organoboronic acids in presence of
CuI and a ligand 2,2¢-dipyridyl was investigated.21 As part of
our ongoing efforts devoted to the synthesis of unsymmetrical
organochalcogenides using a new and practical procedure, herein
we wish to report a novel and highly efficient InBr3-catalyzed direct
cross-coupling reaction of diorgano diselenides and ditellurides
with arylboronic acids in air in the absence of any additive. The
reactions generated the corresponding unsymmetrical diorgano
monoselenides and monotellurides in good to excellent yields
(Scheme 1).
structural motifs, are generally found in a variety of biological and
pharmaceutical molecules1 and in materials science.2 Additionally,
organoselenium compounds have emerged as an exceptional class
of structures that exemplify a role in biochemical processes, serving
as important therapeutic compounds ranging from antiviral and
anticancer agents to naturally occurring food supplements.3 To
synthesize these compounds, a number of synthetic methods have
been explored.4 The generally used method to introduce a selenium
or tellurium moiety into organic molecules is the reaction of
a metal selenolate or tellurolate with appropriate electrophiles,
such as organic halides and acyl chlorides, but aryl halides failed
because of the less reactivity of C(sp2)–X bonds.5
On the other hand, transition metal-catalyzed aryl carbon–
chalcogen bond formation reactions for the preparation of un-
symmetrical organochalcogenides have received more attention.6
For the preparation of aryl chalcogenides, C–S and C–Se coupling
reactions of aryl halides with thiols and selenols have been success-
fully carried out in the presence of palladium7 and nickel,8 as well
as copper,9 as catalyst under basic reaction conditions. Recently,
dichalcogenides are used as substrates in the synthesis of monose-
lenides and tellurides since they are stable in air and are easy
to treat. However, this is limited to alkyl halides.10 In the metal-
catalyzed chalcogenylation of aryl halides with dichalcogenide,
an efficient reductant is often necessary for the generation of the
corresponding anion11 or metal–monochalcogenide complex.12 As
drawbacks, most of these synthetic protocols suffer from lengthy
synthetic steps, harsh reaction conditions, and usually require the
handling of air- and moisture-sensitive reagents.
Over the past few years, indium(III) salts have received in-
creasing attention as a novel type of water-tolerant green Lewis
acid catalyst for organic synthesis with highly chemo-, regio-
Scheme 1
aDepartment of Chemistry, Huaibei Coal Teachers College, Huaibei
Anhui 235000, P R China. E-mail: leiwang@hbcnc.edu.cn; Fax: + 86
(0)561 3090 518; Tel: + 86 (0)561 3802 069
Results and discussion
In our preliminary investigations aimed at the preparation of
4-methoxyphenyl phenyl selenide, we undertook a detailed study
using diphenyl diselenide and 4-methoxyphenyboronic acid as
model coupling partners in order to probe the optimized reaction
conditions with respect to a variety of indium salts and indium
bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of
Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, P R
China
† Electronic supplementary information (ESI) available: Full experimental
details and further results. See DOI: 10.1039/b914533h
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Table 1 Screening of catalysts and solvents for the reaction of arylboronic
Table 2 InBr3-catalyzed C–Se (Te) direct cross-coupling reactionsa
acid with diphenyl diselenidea
ln Br 5mol%
(
)
1
2
R1Y + R2B OH ⎯⎯⎯⎯⎯→R −Y −R
3
(
)
(
)
ꢀ
2
2
DMSO,130
C
4-MeOC H B OH +C6H5SeSeC6H5
(
)
6
4
2
Entry
(R1Y)2
R2B(OH)2
Yield (%)b
ln Catal.
[
]
⎯⎯⎯⎯→4-MeOC6H4SeC6H5
1
2
3
4
5
6
7
8
(C6H5Se)2
(C6H5Se)2
(C6H5Se)2
(C6H5Se)2
(C6H5Se)2
(C6H5Se)2
(C6H5Se)2
(C6H5Se)2
(4-MeOC6H4Se)2
(4-MeOC6H4Se)2
(4-MeOC6H4Se)2
(4-MeOC6H4Se)2
(4-MeOC6H4Se)2
(4-MeOC6H4Se)2
(4-MeOC6H4Se)2
(4-MeOC6H4Se)2
(4-MeOC6H4Se)2
(n-C4H9Se)2
4-MeOC6H4B(OH)2
3-MeOC6H4B(OH)2
2-MeOC6H4B(OH)2
2,4-MeOC6H4B(OH)2
2,6-MeOC6H4B(OH)2
4-MeSC6H4B(OH)2
4-MeO2CC6H4B(OH)2
2-OHCC6H4B(OH)2
C6H5B(OH)2
98
90
95
98
88c
96
85
73
91
72
70
85
93
77
89
83
trace
71
90
98
95
94
95
99
Entry
Indium source (amount)
Solvent/temp.
Yield (%)b
1
2
InCl3 (5 mol%)
InBr3 (5 mol%)
DMSO/130 ◦
DMSO/130 ◦
C
C
82
98
76c
97
40
35
0
0
0
0
81
98
0
0
0
0
0
0
30
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
InI3 (5 mol%)
DMSO/130 ◦
DMSO/130 ◦
DMSO/130 ◦
DMSO/130 ◦
DMSO/130 ◦
DMSO/130 ◦
C
C
C
C
C
C
In(CF3SO3)3 (5 mol%)
In(CH3COO)3 (5 mol%)
InCl (5 mol%)
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
4-ClC6H4B(OH)2
4-BrC6H4B(OH)2
4-FC6H4B(OH)2
InBr (5 mol%)
In metal (5 mol%)
In metal (5 mol%)
InBr3 (2.5 mol%)
InBr3 (10 mol%)
InBr3 (5 mol%)
InBr3 (5 mol%)
InBr3 (5 mol%)
InBr3 (5 mol%)
InBr3 (5 mol%)
InBr3 (5 mol%)
InBr3 (5 mol%)
H2O/100 ◦
C
DMSO/130 ◦
DMSO/130 ◦
C
C
4-MeC6H4B(OH)2
3-MeC6H4B(OH)2
2-MeC6H4B(OH)2
4-t-C4H9C6H4B(OH)2
n-C4H9B(OH)2
4-MeOC6H4B(OH)2
4-MeOC6H4B(OH)2
4-MeOC6H4B(OH)2
3-MeOC6H4B(OH)2
2-MeOC6H4B(OH)2
4-MeO2CC6H4B(OH)2
C6H5B(OH)2
DMF/130 ◦
C
C
DMA/130 ◦
toluene/130 ◦
C
benzene/80 ◦
C
THF/67 ◦
DCE/84 ◦
C
C
(C6H5CH2Se)2
(C6H5Te)2
(C6H5Te)2
(C6H5Te)2
(C6H5Te)2
DMSO/100 ◦
C
a Reaction conditions: 4-methoxyphenylboronic acid (1.00 mmol),
diphenyl diselenide (0.50 mmol), In catalyst (its amount indicated in this
Table) in solvent (1.0 mL) at the indicated temperature for 20 h. b Isolated
yields. c A commercially available Sale WP 650 microwave oven was utilized
at 2450 MHz at 100% power for 0.25 h.
(4-MeOC6H4Te)2
a Reaction conditions: organoboronic acid (1.0 mmol), dichalcogenide
(0.5 mmol), InBr3 (0.05 mmol) in DMSO (1.0 mL), 130 ◦C, 20 h. b Isolated
yields. c At 130 ◦C for 36 h.
metal, and the results are summarized in Table 1. Notably, when
the reaction was ongoing on DMSO at 130 ◦C, InBr3 or InI3
was the judicious catalyst of choice, delivering 4-methoxyphenyl
phenyl selenide exclusively, in very high yield and purity (Table 1,
entries 2 and 3). On the other hand, other indium(III) salts, such as
InCl3, In(CF3SO3)3, and In(CH3COO)3 under the same reaction
conditions, were inferior and generated the desired products in
82, 40 and 35% yields, respectively (Table 1, entries 1, 4 and 5).
However, when InCl, InBr or In metal was used as catalyst, no
desired product was isolated and starting materials were recovered
(Table 1, entries 6–9). Considering that InBr3 is relatively cheap
compared to InI3, it was therefore chosen as catalyst for the
following experiments. With respect to the catalyst loading, when
2.5 mol% of InBr3 was used, the reaction did not go to completion
(Table 1, entry 10), but that a higher loading (5 mol%) of the
catalyst gave a very good result (Table 1, entry 2). However, with
an increased loading of the catalyst up to 10 mol% there was no
increase in the isolated yield of the product (Table 1, entry 11).
Thus, 5 mol% of InBr3 is enough to accomplish this reaction.
We next screened the effect of solvent on the model reaction
by using 5 mol% of InBr3 as catalyst at 130 ◦C, and the nature
of the reaction media significantly affects the reaction. What is
noteworthy is that the choice of DMSO as the solvent was crucial,
and 98% yield of the desired product was isolated (Table 1, entry
2). Unfortunately, none of the desired product was isolated when
the reactions were carried out in N,N-dimethylformamide (DMF),
N,N-dimethylacetamide (DMA), toluene, benzene, tetrahydrofu-
ran (THF) and 1,2-dichloroethane (DCE) (Table 1, entries 12–17).
Microwave irradiation conditions could significantly shorten
the reaction time from 20 h to 0.25 h, but the yield of the product
was reduced from 98% to 76% (Table 1, entry 2). Meanwhile, the
effect of reaction temperature was also investigated. High yield was
obtained when the reaction was carried out in DMSO at 130 C
◦
for 20 h. The reaction at 100 ◦C for 20 h only gave product in 30%
yield (Table 1, entry 18). Thus, the optimized reaction conditions
for the cross-coupling of arylboronic acids with diselenides and
ditellurides are InBr3 (5 mol%) in DMSO at 130 ◦C for 20 h
without any additive.
After obtaining the optimized reaction conditions, the scope
of this transformation on the direct cross-coupling reaction of a
variety of dichalcogenides with different substituted arylboronic
acids was evaluated. The results are delineated in Table 2. At
first, we set out to explore InBr3-catalyzed arylation of diselenides
by the use of various arylboronic acids. In general, the reac-
tion is unaffected by electronic factors and steric hindrance of
substituted groups on benzene rings in arylboronic acids. When
diphenyl diselenide or di(4-methoxyphenyl) diselenide was served
as dichalcogenide partner, a variety of electron-rich, electron-
neutral, and electron-deficient arylboronic acids underwent C–Se
cross-coupling reactions smoothly to generate the corresponding
diaryl monoselenides in good to excellent yields (Table 2, entries
1–16). More distal steric bulk has, as expected, little effect upon
reactivity as demonstrated by the 4-tert-butylphenylboronic acid
case which reacted with di(4-methoxyphenyl) diselenide under the
present reaction conditions to generate the desired product in
83% yield (Table 2, entry 16). Furthermore, sterically demanding
ortho substituents did not hamper the cross-coupling reaction and
the corresponding unsymmetrical diaryl monoselenides were ob-
tained in good yields (Table 2, entries 3–5, 8, and 15). Remarkable
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observation was that more strongly sterically hindered substitution
does not significantly affect the reaction rate or over yield, with
2,6-dimethoxyphenylboronic acid producing good yield of the
expected product within a reasonable time (Table 2, entry 5).
What’s more, the tolerance of potentially reactive functional
group, such as carbonyl and ester group to the described protocol
was remarkable (Table 2, entries 7 and 8). However, only a trace
amount of the product was isolated when an alkylboronic acid,
such as n-C4H9B(OH)2 was used as the substrate (Table 2, entry
17). Fortunately, dialkyl diselenide, such as n-C4H9SeSeC4H9-n,
and dibenzyl diselenide (C6H5CH2SeSeCH2C6H5) also reacted
with 4-methoxyphenylboronic acid to generate the corresponding
products in 71, 90% yields, respectively (Table 2, entries 18
and 19).
Then, we explored the cross-coupling reaction using other
dichalcogenides, such as ditellurides and disulfides. According to
the previously developed procedure, InBr3-catalyzed coupling of
ditellurides with a number of arylboronic acids also underwent
C–Te bond formation smoothly to afford the desired diaryl
monotellurides in good yields, which also were not affected by
electronic effects or steric hindrance of the reaction center (Table 2,
entries 20–24). However, all attempts to use diaryl disulfides as
chalcogen source for directly C–S coupling with arylboronic acids
were met with failure, probably due to the stronger S–S bond, and
starting materials were recovered unconsumed.
via transmetallation to generate PhSeInIII(Br)Ar, which produced
the desired cross-coupling product PhSeAr and InBr according
to path A route via reductive elimination. On the other hand,
PhSeInIII(Br)Ar also could generate the cross-coupling product
PhSeAr and re-generate InBr3 in path B way in the presence
of an oxidant. DMSO, not only as the solvent, but also as the
oxidant in path B might be reduced into dimethyl sulfide under the
present reaction conditions.24 The formed dimethyl sulfide could,
in small amounts, be observed in gas chromatography analysis.
Also we assumed that the generated dimethyl sulfide can stabilize
the formed boronic acid in the transmetallation step.
The generated InBr in path A next reacted with PhSeBr, which
is from initially step to provide PhSeInIIIBr2 via oxidative addition.
The proposed mechanism here also indicated that the cross-
coupling of diorgano diselenide with arylboronic acid is able to
use both selenide groups on diselenide.
Conclusions
In conclusion, we have successfully developed a novel and highly
efficient procedure for the synthesizing unsymmetrical diorgano
monoselenides and diorgano monotellurides in good to excellent
yields through the directly C–Se and C–Te cross-coupling reaction
of arylboronic acids and potassium aryltrifluoroborates with
diorgano diselenides and diphenyl ditelluride in the presence of
a catalytic amount of InBr3 in DMSO without any additive
in air. The present method displays a broad substrate scope,
and is mild, simple, effective and convenient. Furthermore, this
method can tolerate arylation of both organochalcogenide groups
in a dichalcogenide. Althought the similar results including the
reaction conditions, substrate scopes and yields, etc. were achieved
by our previous work using copper catalysts,20 it may open a new
way for using InBr3 as Lewis acid-catalyzed cleavage of Se–Se and
Te–Te bond in diorgano diselenides and ditellurides without any
activating agent and ligand in organic synthesis. Further work on
In-catalyzed organic transformation is being in progress in our
laboratory.
As an alternative to organoboronic acids and esters, organ-
otrifluoroborate salts have emerged as a new class of air-
stable boron derivatives, facile to prepare in high yields and
purities, easy to handle, and feasible to utilize in a number of
useful synthetic processes.22 When the reaction of potassium 4-
methoxyphenyltrifluoroborates with diphenyl diselenide or ditel-
luride was performed under the present reaction conditions, as
expected, excellent yields of the desired products were obtained
(Scheme 2).
Experimental
Scheme 2
For full details, see the ESI.† General remarks: All reactions were
carried out under an air atmosphere. All reagents were purchased
from commercial suppliers and used after further purification.
Products were purified by flash chromatography on 230–400
mesh silica gel, SiO2. All 1H NMR, 13C NMR spectra were
measured on a Bruker Avance NMR spectrometer (400 MHz or
100 MHz, respectively) with CDCl3 as solvent and recorded in ppm
relative to internal tetramethylsilane standard. High resolution
mass spectroscopy data of the product were collected on a Waters
Micromass GCT instrument.
A possible mechanism of InBr3-catalyzed reaction was shown
in Scheme 3. Initially, InBr3 reacted with PhSeSePh to form
PhSeInIIIBr2 and PhSeBr through a heterolytic cleavage of Se–Se
bond.23 The obtained PhSeInIIIBr2 then reacted with ArB(OH)2
General procedure for InBr3-catalyzed preparation of
monochalcogenides from dichalcogenides with arylboronic acids
without any additive: A 10 mL of reaction tube was charged with
dichalcogenide (0.5 mmol), arylboronic acid (1.0 mmol), InBr3
(0.05 mmol), and DMSO (1.0 mL). The reaction vessel was placed
in an oil bath at 130 ◦C. After the reaction was carried out at this
temperature for 20 h, it was cooled to room temperature, diluted
with H2O and extracted twice with Et2O. The organic layers were
combined, dried over Na2SO4, and concentrated to yield the crude
Scheme 3 Possible mechanism of the reaction
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product, which was further purified by flash chromatography
on silica gel (eluant: petroleum ether) to give the desired cross-
coupling product.
9 Selected methods using Cu catalyst: (a) H. Suzuki, H. Abe and A.
Osuka, Chem. Lett., 1981, 151–152; (b) W. R. Bowman, H. Heaney
and P. H. G. Smith, Tetrahedron Lett., 1984, 25, 5821–5824; (c) F. Y.
Kwong and S. L. Buchwald, Org. Lett., 2002, 4, 3517–3520; (d) R. K.
Gujadhur and D. Venkataruman, Tetrahedron Lett., 2003, 44, 81–84.
10 Chalcogenations of alkyl halides or alkenyl borane with dichalcogenide:
(a) A. Kundu and S. Roy, Organometallics, 2000, 19, 105–108; (b) T.
Nishino, M. Okada, T. Kuroki, T. Watanabe, Y. Nishiyama and N.
Sonoda, J. Org. Chem., 2002, 67, 8696–8698; (c) K. Ajiki and K.
Tanaka, Org. Lett., 2005, 7, 4193–4195.
Acknowledgements
We gratefully acknowledge financial support by the National
Natural Science Foundation of China (No. 20772043).
11 C. Millois and P. Diaz, Org. Lett., 2000, 2, 1705–1708.
12 (a) N. Taniguchi and T. Onami, Synlett, 2003, 829–832; (b) N. Taniguchi
and T. Onami, J. Org. Chem., 2004, 69, 915–920; (c) N. Taniguchi,
J. Org. Chem., 2004, 69, 6904–6906; (d) N. Taniguchi, Synlett, 2005,
1687–1690; (e) V. Go´mez-Betez, O. Baldovino-Pantaleo´n, C. Herrera-
Notes and references
´
Alvarez, R. A. Toscano and D. Morales-Morales, Tetrahedron Lett.,
1 (a) K. C. Nicolaou, N. A. Petasis, in Selenium in Natural Products
Synthesis, CIS, Pennsylvania, 1984; (b) S. Patai, Z. Rappoport and C.
Wiley, in The Chemistry of Organic Selenium and Tellurium Compounds,
1987, vol. 2; (c) T. G. Back, in Organoselenium Chemistry: A Practical
Approach, Oxford University Press, New York, 1999; (d) G. Liu, J. R.
Huth, E. T. Olejniczak, R. Mendoza, P. DeVries, S. Leitza, E. B. Reilly,
G. F. Okasinski, S. W. Fesik and T. W. Geldern, J. Med. Chem., 2001,
44, 1202–1210; (e) G. Mugesh, W. W. Mont and H. Sies, Chem. Rev.,
2001, 101, 2125–2179; (f) M. G. Szczepina, B. D. Johnston, Y. Yuan, B.
Svensson and B. M. Pinto, J. Am. Chem. Soc., 2004, 126, 12458–12469.
2 (a) Y. Okamoto, in The Chemistry of Organic Selenium and Tellurium
Compounds, ed. S. Patai and Z. Rappoport, Wiley, Chichester, U.K.,
1986, vol. 1, ch. 10; (b) J. Hellberg, T. Remonen, M. Johansson, O.
Ingana¨s, M. Theander, L. Engman and P. Eriksson, Synth. Met., 1997,
84, 251–252; (c) T. Ando, T. S. Kwon, A. Kitagawa, T. Tanemura, S.
Kondo, H. Kunisada and Y. Yuki, Macromol. Chem. Phys., 1996, 197,
2803–2810.
2006, 47, 5059–5062; (f) S. Kumar and L. Engman, J. Org. Chem.,
2006, 71, 5400–5403; (g) D. Cheng and W. Bao, Synlett, 2006, 1786–
1788; (h) S. I. Fukuzawa, D. Tanihara and S. Kikuchi, Synlett, 2006,
2145–2147.
13 Reviews for indium Lewis acids: (a) C. G. Frost and K. K. Chauhan,
J. Chem. Soc., Perkin Trans., 1, 2000, 3015–3019; (b) F. Fringuelli, O.
Piermatti, F. Pizzo and L. Vaccaro, Curr. Org. Chem., 2003, 7, 1661–
1689; (c) C. G. Frost and J. P. Hartley, Mini-Rev. Org. Chem., 2004, 1,
1–7; (d) Z.-H. Zhang, Synlett, 2005, 711–712.
14 (a) Y.-C. Teo and T.-P. Loh, Org. Lett., 2005, 7, 2539–2541; (b) G. Babu
and P. T. Perumal, Tetrahedron Lett., 1998, 39, 3225–3228.
15 T. Miyai, Y. Onishi and A. Baba, Tetrahedron Lett., 1998, 39, 6291–
6294.
16 T.-P. Loh and L.-L. Wei, Tetrahedron Lett., 1998, 39, 323–326.
17 (a) G. K. Friestad, C. S. Korapala and H. Ding, J. Org. Chem., 2006,
71, 281–289; (b) Y. Onishi, T. Ito, M. Yasuda and A. Baba, Eur. J. Org.
Chem., 2002, 1578–1581.
18 Allylation of carbonyl compounds with allyltributylstannanes: (a) Y.-
U. Teo, J.-D. Goh and T.-P. Loh, Org. Lett., 2005, 7, 2743–2745; (b) J.
Lu, S.-J. Ji, Y.-C. Teo and T.-P. Loh, Org. Lett., 2005, 7, 159–161;
(c) J. A. Marshall and K. W. Hinkle, J. Org. Chem., 1995, 60, 1920–
1921; (d) Other reactions, see: S. Harada, S. Handa, S. Matsunaga
and M. Shibasaki, Angew. Chem., Int. Ed., 2005, 44, 4365–4368; (e) R.
Yanada, S. Obika, Y. Kobayashi, T. Inokuma, M. Oyama, K. Yanada
and Y. Takemoto, Adv. Synth. Catal., 2005, 347, 1632–1642; (f) R.
Yanada, S. Obika, M. Oyama and Y. Takemoto, Org. Lett., 2004, 6,
2825–2828; (g) A. P. Dobbs, S. J. J. Guesne´, S. Martinovic´, S. J. Coles and
M. B. Hursthouse, J. Org. Chem., 2003, 68, 7880–7883; (h) Y. Onishi,
D. Ogawa, M. Yasuda and A. Baba, J. Am. Chem. Soc., 2002, 124,
13690–13691; (i) Y. S. Cho, H. Y. Kim, J. H. Cha, A. N. Pae, H. Y. Koh,
J. H. Choi and M. H. Chang, Org. Lett., 2002, 4, 2025–2028; (j) M.
Yasuda, Y. Onishi, M. Ueba, T. Miyai and A. Baba, J. Org. Chem.,
2001, 66, 7741–7744.
19 (a) B. C. Ranu, T. Mandal and S. Samanta, Org. Lett., 2003, 5, 1439–
1441; (b) B. C. Ranu and T. Mandal, J. Org. Chem., 2004, 69, 5793–5795.
20 L. Wang, M. Wang and F. Huang, Synlett, 2005, 2007–2010.
21 N. Taniguchi, J. Org. Chem., 2007, 72, 1241–1245.
22 (a) G. A. Molander and M. Ribagorda, J. Am. Chem. Soc., 2003, 125,
11148–11149; (b) G. A. Molander and M. R. Rivero, Org. Lett., 2002,
4, 107–109; (c) G. A. Molander and B. J. Biolatto, J. Org. Chem., 2003,
68, 4302–4314; (d) R. A. Batey and A. N. Thadani, Org. Lett., 1999,
1, 1683–1686; (e) A. N. Thadani and R. A. Batey, Org. Lett., 2002, 4,
3827–3830; (f) G. W. Kabalka, B. Venkataiah and G. Dong, Org. Lett.,
2003, 5, 3803–3805; (g) T. E. Barder and S. L. Buchwald, Org. Lett.,
2004, 6, 2649–2652.
3 (a) A. Krief and M. Derock, Tetrahedron Lett., 2002, 43, 3083–
3086; (b) D. L. Klayman and W. H. H. Gu¨nther, in Organoselenium
Compounds: Their Chemistry and Biology, Wiley-Interscience, New
York, 1973.
4 For selected reviews: (a) B. M. Trost and I. Fleming, in Comprehensive
Organic Synthesis, Pergamon Press, New York, 1991, vol. 4; (b) A.
Krief, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel,
F. G. A. Stone and G. Wilkinson, Pergamon Press, New York, 1995,
vol. 11, ch. 13; (c) N. Miyaura, in Metal-Catalyzed Cross-Coupling
Reactions, vol. 1, ed. A. Meijere, F. Diederich), Wiley-VCH, Weinheim,
2004, pp 41–123; (d) H. R. Ahn, Y. A. Cho, D.-S. Kim, J Chin, Y.-S.
Gyoung, S Lee, H Kang and J Ham, Org. Lett., 2009, 11, 361–364;
(e) V. P. Reddy, A. V. Kumar, K Swapna and K. R. Rao, Org. Lett.,
2009, 11, 951–953.
5 (a) W. Bao, Y. Zheng, Y. Zhang and J. Zhou, Tetrahedron Lett., 1996,
37, 9333–9334; (b) S. Fukuzawa, Y. Niimoto, T. Fujinami and S. Sakai,
Heteroat. Chem., 1990, 1, 491–495; (c) M. Sakakibara, K. Katsumata,
Y. Watanabe, T. Toru and Y. Ueno, Synthesis, 1992, 377–379; (d) M. R.
Detty, J. Org. Chem., 1980, 45, 274–279; (e) L. Wang and Y. Zhang,
Heteroat. Chem., 1999, 10, 203–208.
6 For selected reviews, see: (a) S. V. Ley and A. W. Thomas, Angew.
Chem., Int. Ed., 2003, 42, 5400–5449; (b) T. Kondo and T. Mitsudo,
Chem. Rev., 2000, 100, 3205–3220.
7 For selected papers using Pd catalyst: (a) T. Migita, T. Shimizu, Y.
Asami, J. Shiobara and M. Kosugi, Bull. Chem. Soc. Jpn., 1980, 53,
1385–1389; (b) M. Kosugi, T. Ogata, M. Terada, H. Sano and T. Migita,
Bull. Chem. Soc. Jpn., 1985, 58, 3657–3658; (c) D. Barran˜ano and J. F.
Hartwig, J. Am. Chem. Soc., 1995, 117, 2937–2938; (d) P. G. Ciattini,
E. Morera and G. Ortar, Tetrahedron Lett., 1995, 36, 4133–4136; (e) N.
Zheng, J. C. McWilliams, F. J. Fleitz, J. D. Armstrong, III and R. P.
Volante, J. Org. Chem., 1998, 63, 9606–9607; (f) Y. Nishiyama, K.
Tokunaga and N. Sonoda, Org. Lett., 1999, 1, 1725–1727; (g) T. Itoh
and T. Mase, Org. Lett., 2004, 6, 4587–4590.
23 S. Usugi, H. Yorimitsu, H. Shinokubo and K. Oshima, Org. Lett., 2004,
6, 601–603.
24 (a) A. J. Mancuso and D. Swern, Synthesis, 1981, 165–185; (b) B.
Karimi, H. Hazarkhani and D. Zareyee, Synthesis, 2002, 2513–2516;
(c) L. W. Bieber, M. F. Silva and P. H. Menezes, Tetrahedron Lett., 2004,
45, 2735–2737.
8 The synthetic method using Ni catalyst: (a) H. J. Cristau, B. Chabaud,
A. Cheˆne and H. Christol, Synthesis, 1981, 892–894; (b) K. Takagi,
Chem. Lett., 1987, 2221–2224.
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