CuI/Oxalic Diamide-Catalyzed Cross-Coupling of Thiols with Aryl Bromides and Chlorides

Article abstract of DOI:10.1002/chem.201701671

We report a general copper-catalyzed cross-coupling of thiols with aryl halides by using N-aryl-N′-alkyl oxalic diamide (L3) or N,N′-dialkyl oxalic diamide (L5) as the ligand. Both aryl and alkyl thiols can be coupled with unactivated aryl bromides and chlorides to give the desired products in good yields. Furthermore, this system features a broad substrate scope and good tolerance of functional groups. Importantly, the oxalic diamides are stable and can be prepared easily from commercially available and cheap starting materials.

Full text of DOI:10.1002/chem.201701671

A Journal of
Accepted Article
Title: CuI/Oxalic Diamide-Catalyzed Cross-Coupling of Thiols with Aryl
Bromides and Aryl Chlorides
Authors: Chin-Fa Lee, Chia-Wei Chen, Yi-Ling Chen, Daggula
Mallikarjuna Reddy, Kai Du, Chao-En Li, Bo-Hao Shih, and
Yung-Jing Xue
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To be cited as: Chem. Eur. J. 10.1002/chem.201701671
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10.1002/chem.201701671
Chemistry - A European Journal
FULL PAPER
DOI: 10.1002/chem.200((will be filled in by the editorial staff))
CuI/Oxalic Diamide-Catalyzed Cross-Coupling of Thiols with Aryl Bromides and
Aryl Chlorides
Chia-Wei Chen,[a] Yi-Ling Chen,[a] Daggula Mallikarjuna Reddy,[a] Kai Du,[a] Chao-En Li,[a] Bo-
Hao Shih,[a] Yung-Jing Xue,[a] and Chin-Fa Lee*[a]
Abstract: We report a general copper- first copper-catalyzed coupling of thiols prepared easily from commercially
catalyzed cross-coupling of thiols with with unactivated aryl chlorides. available cheap starting materials.
aryl bromides and aryl chlorides by Furthermore, this system features broad
using N-aryl-N’-alkyl oxalic diamide substrate scope and good tolerance of
(L3) or N,N’-dialkyl oxalic diamide (L5) functional groups. Importantly, the
as the ligands. Remarkably, this is the oxalic diamides are stable and can be
Keywords: oxalic diamide
bromide • aryl chloride • thiol • thioether
• aryl
copper catalysis. Therefore, the development of a general copper-
catalyzed coupling of thiols with aryl chlorides is highly desirable.
Recently, Ma and co-workers reported the copper-catalyzed
amination[19,20] and etherification[21,22] of aryl chlorides by using oxalic
diamide as ligand. Oxalic diamides are stable, and can be easily prepared
from cheap commercially available oxalyl chloride [for symmetrical,
Scheme1, (a)] or ethylchlorooxalate [for unsymmetrical, Scheme 1, (b)]
with amines .[19,22] As part of our ongoing interest in C-S bond forming
reaction,[11b,13,16f-j,23] we herein report a general copper-catalyzed cross-
coupling reaction of thiols with aryl bromides and aryl chlorides.
Interestingly, N,N’-diaryl oxalamide is less reactive than N,N’-dialkyl
oxalic diamide and N-aryl-N’-benzyl oxalic diamide for coupling with
aryl bromides. Surprisingly, N,N’-dialkyl oxalic diamide (L5) is a
powerful ligand for copper-catalyzed coupling of thiols with aryl
chlorides. To the best of our knowledge, this is the first general method
for copper-catalyzed thioetherification of aryl chlorides.
Introduction
Thioethers are an important class of motifs present in numerous bioactive
molecules, organic synthesis and materials science.[1-4] Therefore, the
synthesis of thioethers has received considerable attention during the past
decades.[1-14] Transition-metal-catalyzed coupling reaction of aryl halides
with thiols is a powerful strategy for the preparation of thioethers.[5-14]
Migita and co-workers first reported the cross-coupling reaction of aryl
halides and thiols by using Pd(PPh3)4 as a catalyst.[6a] Many nice works
have later been achieved under palladium catalysis.[6b,6c,7] Catalytic
systems based on other transition metals such as nickel[8], cobalt,[9] iron,[10]
rhodium,[11] gold,[12] manganese[13] and iridium[14] have also been
introduced for C-S bond cross-coupling reaction. Most of these catalytic
systems however suffer from several limitations, such as high cost and
high toxicity of catalysts and ligands. Although aryl chloride is the most
attractive aryl halide for metal-catalyzed cross-coupling reactions,
however, aryl chloride is less reactive than aryl bromides and iodides.[15]
Palladium is the most prominent catalyst for the coupling of thiols with
aryl chlorides.[7]
Copper salt has commonly applied for C-S cross-coupling reactions
because of its low cost.[16-18] Aryl iodides,[16] aryl bromides[17] and
activated aryl chlorides[18] are well-known in this area. Unactivated aryl
chloride has not been well developed for the coupling with thiols through
[*]
C.-W. Chen, Y.-L. Chen, Dr. D. M. Reddy, K. Du, C.-E. Li,
B.-H. Shih, Y.-J. Xue, Prof. Dr. C.-F. Lee
Department of Chemistry
Scheme 1. Synthesis of oxalic diamides.
National Chung Hsing University
Taichung, Taiwan 402, R.O.C
E-mail: cfalee@dragon.nchu.edu.tw
Supporting information for this article is given via a link at the end of the
document.((Please delete this text if not appropriate))
1
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Table 1. Reaction conditions optimization.[a,b]
Results and Discussion
Initially, thiophenol (1a) and 4-bromotoluene (2a) were chosen as
model substrates to optimize the reaction conditions. When N,N’-bis(2-
biphenyl) oxalic diamide, L1 was used as a ligand, the target was obtained
in 17% yield (Table 1, entry 1). When N-aryl-N’-benzyl oxalic diamide,
L2 was employed as a ligand, the desired product was afforded in 94%
yield (Table 1, entry 2). Encouraged by this result, we then examined
other oxalic diamides (L3-L5, Table 1, entries 3-5). Interestingly, n-
hexyl-substituted oxalic diamides L3 and L5 showed excellent reactivity
for this coupling reaction (Table 1, entries 3 and 5, respectively). When
hexyl was replaced by bulkier cyclohexyl ligand (L4), the yield of the
product was dropped to 49% (Table 1, entry 4). Replacing CuI with other
catalysts such as Cu2O, CuCl2, CuBr and CuCl gave little inferior results
compared with CuI (Table 1, entries 6-9). When DMSO, DMF and NMP
were used as solvents, products 3a and 3a’ in different ratio were detected
(Table 1, entries 10-12), the formation of 3a’ suggests a benzyne
intermediate was involved.[16h] We next used different bases for this
system, bases such as KOMe, Cs2CO3, K3PO4 and NaOtBu gave the
product 3a in lower yields (Table 1, entries 13-16). A lower yield was
obtained when the loading of ligand was decreased to 5 mol% (Table 1,
entry 17). Trace amount of product was detected when the reaction was
carried out in the absence of ligand (Table 1, entry 18). Shorter reaction
times diminished the product yield to 78% yield (Table 1, entry 19).
Scheme 2 summaries the copper-catalyzed C-S coupling reaction. A
variety of para-substituted aryl bromides bearing either electron-donating
or electron-withdrawing groups were coupled with thiophenol to afford
the coupling products 3b-3g in good to excellent yields. Aryl bromides
with ortho- and meta-substituents were also worked to provide thioethers
3h-3j in good yields. Importantly, 3h was obtained as the sole product in
95% yield by using L5 as a ligand, however, the regio-isomer 3h’
(through benzyne) was observed when L3 was used as a ligand. When 1-
naphthyl bromide was used as a coupling partner, 3k was obtained in 74%
yield. Aryl bromides with bulky groups such as tert-butyl at 3- and 5-
positions were tolerated and afforded the thioethers 3j and 3l in good
yields. Heterocycles such as 3-bromopyridine and 3-bromothiophene
were also successfully coupled with thiophenol, gave the corresponding
thioethers (3m and 3n) in excellent yields.
Entry
1
Catalyst
CuI
Ligand
L1
L2
L3
L4
L5
L3
L3
L3
L3
L3
L3
L3
L3
L3
L3
L3
L3
-
Base
Solvent
Yield of 3a
17
KOtBu
KOtBu
KOtBu
KOtBu
KOtBu
KOtBu
KOtBu
KOtBu
KOtBu
KOtBu
KOtBu
KOtBu
KOMe
Cs2CO3
K3PO4
NaOtBu
KOtBu
KOtBu
KOtBu
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
DMSO
2
CuI
94
3
CuI
99
4
CuI
49
5
CuI
98
6
Cu2O
CuCl2
CuBr
CuCl
CuI
96
7
95
8
95
9
93
10
11
12
13
14
15
16
17
18
19
99[c]
95[d]
41[e]
45
CuI
DMF
CuI
NMP
CuI
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
CuI
trace
12
CuI
CuI
20
CuI
72[f]
trace
78[g]
CuI
CuI
L3
[a] Reaction conditions: 1a (1.0 mmol), 2a (1.3 equiv), catalyst (5 mol%), ligand (10
mol%), base (1.7 equiv) and solvent (1.5 mL) under atmosphere of argon at 110 ºC for
24 h. [b] Isolated yields. [c] Ratio of 3a and 3a’ is 1:1. [d] Ratio of 3a and 3a’ is 8:2. [e]
Ratio of 3a and 3a’ is 8:2. [f] 5 mol% of L3 used. [g] Reaction run for 12 h. 1,4-Dioxane
= 1,4-dioxacyclohexane; DMSO = dimethyl sulfoxide; DMF = N,N-dimethylformamide;
NMP = N-methyl-2-pyrrolidone.
Since the performance of L5 is better than L3 in Scheme 2, we
decided to use L5 as a ligand to survey the coupling reaction of other aryl
thiols with aryl bromides, the results are summarized in Scheme 3. A
variety of para-substituted aryl thiols consisting of either electron-
donating or electron-withdrawing groups were worked smoothly with aryl
bromides to afford the targets 3a, 3e, 3f and 3o in 56-95% yields.
Sterically hindered aryl thiols such as 2-methylthiophenol and 2-
chlorothiophenol were successfully coupled with bromobenzene and
delivered the desired products 3i and 3p in high yields. Remarkably,
unprotected 2-aminothiophenol was reacted with bromobenzene to
provide 3q in 91% yield. 1-naphthylthiol was coupled with
bromobenzene to obtain 3k in almost quantitative yield. Heterocycles
such as pyridine-2-thiol was coupled with bromobenzene to give thioether
(3r) in 92% yield. Aryl bromides with electron-rich and electron-deficient
were also conducted with various aryl thiols to afford the corresponding
thioethers 3s-3u in good yields. In general, alkyl thiol is less reactive than
aryl thiol for copper-catalyzed C-S bond formation.[23b] A 10% of product
5a was isolated when 2-methyl-1-propanethiol reacted with
bromobenzene at 110 ºC. To our delight, a 74% yield was achieved when
the reaction was performed at 135 °C employing 2.5 equiv of base.
Several of alkyl thiols including linear, cyclic and branched thiols were
reacted with aryl bromides to give the thioethers in good to excellent
yields (Scheme 4).
Scheme 2. Scope of aryl bromides to couple with thiophenol. [a] Using L5 as ligand.
Yields of the isolated products are given. See the Supporting Information for details.
We next turned our attention to the challenging cross-coupling
reaction of aryl chlorides with thiols. 4-Chlorotoluene (6a) and thiophenol
(1a) were selected as the substrates to study the optimized reaction
conditions. As shown in Table 2, only 15% of product was observed
(Table 2, entry 1) when the reaction was performed under the best
conditions used for aryl bromides. To our delight, when reaction
temperatures increased to 120 °C and 135 °C, as a result, yields of the
product 3a were improved to 48% and 67% (Table 2, entries 2 and 3,
respectively). After screening ligands (entries 4-7) and bases (entries 8-
10), L5 and KOtBu were found to be the best ligand and base. Increased
amount of KOtBu to 2.5 equiv, resulted the formation of 3a and 3a’ in
2
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10.1002/chem.201701671
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65:35 ratio in 91% yield. (Table 2, entry 11). To our delight, 3a’ was
in moderate yields. Not only aryl thiols but also alkyl thiols successfully
inhibited when the reaction was performed in toluene (Table 2, entry 12).
coupled with aryl chlorides and gave the products (5) in good yields.
Scheme 3. Scope of aryl bromides with thiophenols. Yields of the isolated products are
given. See the Supporting Information for details.
Scheme 5. Scope of aryl chlorides with thiols. Yields of the isolated products are given.
[a] Ratio of 3k and 3w is 8:2. See the Supporting Information for details.
Conclusion
In conclusion, we have developed a general copper/oxalic diamide
catalytic system for the coupling reaction of thiols with aryl bromides and
aryl chlorides. There are several advantages to this system: (1) oxalic
diamides are stable, and can be easily prepared from cheap starting
materials; (2) Functional groups including fluoro, trifluoromethyl,
unprotected amine, chloro and heterocycles are all tolerated by the
reaction conditions employed; (3) sterically substrates were also proved
to be good coupling partners. Studies on the mechanism and application
of this catalytic system are in progress.
Scheme 4. Scope of aryl bromides with alkyl thiols. Yields of the isolated products are
given. [a] At 110 °C. [b] Ratio of 5e and 5e’ is 9:1. See the Supporting Information for
details.
Table 2. Reaction conditions optimization.[a,b]
Experimental
General information: all commercial chemicals were used as received except
where noted. All Cu-catalyzed experiments were performed under an
atmosphere of argon using standard sealed tube unless otherwise stated. Flash
chromatography was performed on Merck silica gel 60 (230–400 mesh). NMR
spectra were recorded on a Varian Unity Inova-600 or a Varian Mercury-400
instrument using CDCl3 as a solvent. Chemical shifts are reported in parts per
million (ppm) and referenced to the residual solvent resonance. Coupling
constant (J) are reported in hertz (Hz). Standard abbreviations indicating
multiplicity were used as follows: s = singlet, d = doublet, t = triplet, dd =
double of doublet, q = quartet, m = multiplet, b = broad. Melting points (M.P.)
were determined using a Büchi 535 apparatus and are reported uncorrected.
Entry
1
Ligand
L5
Base (equiv.)
KOtBu (1.7)
KOtBu (1.7)
KOtBu (1.7)
KOtBu (1.7)
KOtBu (1.7)
KOtBu (1.7)
KOtBu (1.7)
LiOtBu (1.7)
NaOtBu (1.7)
Cs2CO3 (1.7)
KOtBu (2.5)
KOtBu (2.5)
Solvent
Yield of 3a
15[c]
48[d]
67
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
toluene
2
L5
3
L5
4
L1
NR
5
L2
NR
6
L3
15
7
L4
NR
8
L5
NR
GC-MS analyses were performed on
a GC-MS analysis on Agilent
9
L5
trace
NR
91[e]
Technologies 5977A GC equipped with Agilent 7890B MS. High-resolution
mass spectra were carried out on a Jeol JMS-HX 110 spectrometer by the
services at the National Chung Hsing University. Ligands L1-L3 and L5 were
prepared following the literature procedure.[22,24]
10
11
12
L5
L5
L5
84
[a] Reaction conditions: 1a (1.0 mmol), 6a (1.3 equiv), CuI (5 mol%), ligand (10 mol%),
base and solvent (1.5 mL) under atmosphere of argon at 135 °C for 24 h. [b] Isolated
yields. [c] Reaction performed at 110 °C. [d] Reaction performed at 120 °C. [e] Ratio of
3a and 3a’ is 65:35.
Analysis: NMR spectra were recorded on a Varian Unity Inova-600 or a
Varian Mercury-400 instrument using CDCl3 as a solvent. Chemical shifts are
reported in parts per million (ppm) and referenced to the residual solvent
resonance. Coupling constant (J) are reported in hertz (Hz). Standard
abbreviations indicating multiplicity were used as follows: s = singlet, d =
doublet, t = triplet, dd = double doublet, q = quartet, quin = quintet, m =
multiplet, b = broad. GC-MS analysis were performed on a Agilent
Technologies 5977A GC equipped with Agilent 7890B MS. High-resolution
mass spectra were carried out on a Jeol JMS-HX 110 spectrometer by the
services at the National Chung Hsing University.
With the optimized conditions established, we then explored the
substrate scope of the reaction (Scheme 5). Functional groups such as
fluoro, trifluoromethyl, chloro and thiophene are all suitable as coupling
partners. When electron-rich thiols were conducted with aryl chlorides,
the corresponding thioethers were delivered in good yields, whereas aryl
chlorides coupled with electron-deficient thiols such as 4-fluoro
thiophenol and 4-trifluoromethyl thiophenol, the products were obtained
3
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10.1002/chem.201701671
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General procedure for Table 1
Lowe, Polym. Chem. 2010, 1, 17; d) J. Liu, J. Yang, Q. Yang, G. Wang, Y. Li,
Adv. Funct. Mater. 2005, 15, 1297.
A 5 mL sealable tube equipped with a Teflon-coated magnetic stir bar was
charged with catalyst (5 mol%), ligand (10 mol%) and base (1.7 equiv). The
tube was then evacuated and backfilled with argon (this sequence was repeated
three times), and 4-bromotoluene (0.160 mL, 1.3 mmol), thiophenol (0.102
mL, 1.0 mmol) and solvent (1.5 mL ) were then added into the tube via syringe.
The reaction mixture was stirred at 110 °C in an oil bath for 24 h. After cooling
to room temperature, the crude product was diluted with ethyl acetate (~40
mL), and filtered through silica gel pad. Then the filtrate was concentrated in
vacuum. The residue was purified by flash chromatography (SiO2, hexane) to
yield 3a.
[3] a) S. W. Kaldor, V. J. Kalish, J. F. Davies, II, B. V. Shetty, J. E. Fritz, K. Appelt,
J. A. Burgess, K. M. Campanale, N. Y. Chirgadze, D. K. Clawson, B. A.
Dressman, S. D. Hatch, D. A. Khalil, M. B. Kosa, P. P. Lubbehusen, M. A.
Muesing, A. K. Patick, S. H. Reich, K. S. Su, J. H. Tatlock, J. Med. Chem. 1997,
40, 3979; b) S. F. Nielsen, E. O. Nielsen, G. M. Olsen, T. Liljefors, D. Peters, J.
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Reilly, G. F. Okasinski, S. W. Fesik, T. W. von Geldern, J. Med. Chem. 2001, 44,
1202.
The representative example of Table 1
Phenyl(p-tolyl)sulfane (3a):[25] Following the condition A, using 4-
bromotoluene (0.160 mL, 1.3 mmol), CuI (9.5 mg), L5 (25.4 mg), KOtBu
(0.186g, 1.7 mmol), thiophenol (0.102 mL, 1.0 mmol) and dioxane (1.5 mL),
then purified by column chromatography (SiO2, hexane) to provide 3a as a
[5] a) Metal-Catalyzed Cross-Coupling Reactions Vol. 1 (Eds.: A. de Meijere, F.
Diederich), Wiley-VCH, Weinheim, 2004; b) Handbook of Organopalladium
Chemistry for Organic Synthesis Vol. 1-2 (Eds.: E.-i. Negishi), Wiley-Interscience,
New York, 2002; c) Catalyzed Carbon-Heteroatom Bond Formation (Eds.: A. K.
Yudin, A. K), Wiley-VCH, Weinheim, 2011.
1
yellow liquid (196 mg, 98% yield). H NMR (400 MHz, CDCl3): δ 2.28 (s,
3H), 7.06-7.13 (m, 3H), 7.17-7.28 (m, 6H); 13C NMR (100 MHz, CDCl3): δ
21.0, 126.2, 128.9, 129.6, 129.9, 131.2, 132.2, 137.0, 137.4.
[6] a) T. Migita, T. Shimizu, Y. Asami, J. Shiobara, Y. Kato, M. Kosugi, Bull. Chem.
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4587.
General procedure for Table 2-4 and Table 6:
[7] a) M. Murata, S. L. Buchwald, Tetrahedron 2004, 60, 7397; b) M. A. Fernández-
Rodríguez, Q. Shen, J. F. Hartwig, Chem. Eur. J. 2006, 12, 7782; c) J. L. Farmer,
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Condition A: A 5 mL sealable tube equipped with a Teflon-coated magnetic
stir bar was charged with CuI (9.5 mg), L5 (25.4 mg), (hetero)aryl halide (if
solid) (1.3 mmol), thiolphenol (if solid) (1.0 mmol) and KOtBu (1.7 mmol for
condition A, 2.5 mmol for condition B). The tube was then evacuated and
backfilled with argon (this sequence was repeated three times), and
(hetero)aryl halide (if liquid) (1.3 mmol), thiolphenol (if liquid) (1.0 mmol)
and solvent (1.5 mL dioxane ) were then added into the tube via syringe. The
reaction mixture was stirred at 110 °C (condition A) or 135 °C (condition B)
in an oil bath for 24 h. After cooling to room temperature, the crude product
was diluted with ethyl acetate (~40 mL), and filtered through silica gel pad.
Then the filtrate was concentrated in vacuum. The residue was purified by
flash chromatography (eluting with ethyl acetate/hexane) to afford the
corresponding thioethers.
[11] a) S. D. Timpa, C. J. Pell, O. V. Ozerov, J. Am. Chem. Soc. 2014, 136, 14772; b)
C.-S. Lai. H.-L. Kao, Y.-J. Wang, C.-F. Lee, Tetrahedron Lett. 2012, 53, 4365; c)
M. Arisawa, T. Suzuki, T. Ishikawa, M. Yamaguchi, J. Am. Chem. Soc. 2008, 130,
12214.
[12] M. Jean, J. Renault, P. van de Weghe, N. Asao, Tetrahedron Lett. 2010, 51, 378.
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Chem. 2017, 129, 892.
Condition C (for all aryl chlorides): A 5 mL sealable tube equipped with a
teflon-coated magnetic stir bar was charged with CuI (9.5 mg), L5 (25.4 mg),
(hetero)aryl halide (if solid) (1.3 mmol), thiolphenol (if solid) (1.0 mmol) and
KOtBu (2.5 mmol). The tube was then evacuated and backfilled with argon
(this sequence was repeated three times), and (hetero) aryl halide (if liquid)
(1.3 mmol), thiolphenol (if liquid) (1.0 mmol) and toluene (1.5 mL) were then
added into the tube via syringe. The reaction mixture was stirred at 135 °C in
an oil bath for 24 h. After cooling to room temperature, the crude product was
diluted with ethyl acetate (~40 mL), and filtered through silica gel pad. Then
the filtrate was concentrated in vacuum. The resulting residue was purified by
flash chromatography (eluting with ethyl acetate/hexane) to afford the
corresponding thioethers.
[15] a) A. F. Littke, G. C. Fu, Angew. Chem. Int. Ed. 2002, 41, 4176; Angew.
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Published online: ((will be filled in by the editorial staff))
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Chemistry - A European Journal
Cross-Coupling Reactions

Chia-Wei Chen, Yi-Ling Chen,
Daggula Mallikarjuna Reddy, Kai
Du, Chao-En Li, Bo-Hao Shih,
Yung-Jing Xue and Chin-Fa Lee*
We report
a general copper-catalyzed
CuI/Oxalic Diamide Catalyzed Cross-
Coupling of Thiols with Aryl
bromides and Aryl Chlorides
cross-coupling of thiols with aryl bromides
and aryl chlorides by using N-aryl-N’-alkyl
oxalic diamide (L3) or N,N’-dialkyl oxalic
diamide (L5) as the ligands. Both aryl- and
alkyl thiols can be coupled with unactivated
aryl bromides and unactivated aryl
chlorides to give the desired products in
good yields. Furthermore, this system
features broad substrate scope and good
tolerance of functional groups. Importantly,
the oxalic diamides are stable and can be
prepared
easily
from
commercially
available cheap starting materials.
6
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Supporting Information
CuI/Oxalic Diamide-Catalyzed Cross-Coupling of Thiols with Aryl
Bromides and Aryl Chlorides
Chia-Wei Chen, Yi-Ling Chen, Daggula Mallikarjuna Reddy, Kai Du, Chao-En Li, Bo-
Hao Shih, Yung-Jing Xue, and Chin-Fa Lee*
Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan
E-mail: cfalee@dragon.nchu.edu.tw
NMR spectra for new compounds
[*]
C.-W. Chen, Y.-L. Chen, Dr. D. M. Reddy, K. Du, C.-E. Li,
B.-H. Shih, Y.-J. Xue, Prof. Dr. C.-F. Lee
Department of Chemistry
National Chung Hsing University
Taichung, Taiwan 402, R.O.C
E-mail: cfalee@dragon.nchu.edu.tw
Supporting information for this article is given via a link at the end of the
document.((Please delete this text if not appropriate))
7
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Chemistry - A European Journal
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Chemistry - A European Journal
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Chemistry - A European Journal
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Chemistry - A European Journal
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