Amide-Directed Bay-Region Two-Step Annulative π-Extension (APEX) of Biphenyls and Terphenyls with Diaryliodonium Salts: Efficient Access to Polycyclic Aromatic Hydrocarbons

Article abstract of DOI:10.1002/adsc.201901010

An amide-directed bay-region two-step annulative π-extension reaction of biphenyls and terphenyls with diaryliodonium salts has been developed. A variety of polycyclic aromatic hydrocarbons can be synthesized efficiently according to this approach, such as triphenylene, dibenzo[fg,op]tetracene, and tribenzo[fg,ij,rst]pentaphene derivatives. (Figure presented.).

Full text of DOI:10.1002/adsc.201901010

Title: Amide-Directed Bay-Region Two-Step Annulative π-Extension
APEX) of Biphenyls and Terphenyls with Diaryliodonium Salts:
(
Efficient Access to Polycyclic Aromatic Hydrocarbons
Authors: Qiong Peng, Wen Zhang, Ke Zhao, Yu Du, Chun Feng, Bi-Qin
Wang, Dong-Mei Fang, Xiao-Zhen Chen, Hai-Liang Ni, and
Shi-Kai Xiang
This manuscript has been accepted after peer review and appears as an
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To be cited as: Adv. Synth. Catal. 10.1002/adsc.201901010
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Advanced Synthesis & Catalysis
10.1002/adsc.201901010
FULL PAPER
DOI: 10.1002/adsc.201((will be filled in by the editorial staff))
Amide-Directed Bay-Region Two-Step Annulative π-Extension
APEX) of Biphenyls and Terphenyls with Diaryliodonium Salts:
Efficient Access to Polycyclic Aromatic Hydrocarbons
(
a†
a†
a
a
a
a
Qiong Peng, Wen Zhang, Ke Zhao, Yu Du, Chun Feng, Bi-Qin Wang, Dong-Mei
b
b
a
a
Fang, Xiao-Zhen Chen, Hai-Liang Ni, * and Shi-Kai Xiang *
a
College of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610068, P. R. of China
E-mail: xiangsk@sicnu.edu.cn (S.-K. X.); nihl@sicnu.edu.cn (H.-L. N.)
Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, P. R. of China
The two authors contributed equally to this work
b
†
Received: ((will be filled in by the editorial staff))
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/adsc.201######.((Please
delete if not appropriate))
Abstract. An amide-directed bay-region two-step annulative
π-extension reaction of biphenyls and terphenyls with Keywords: Annulative π-Extension; Polycyclic Aromatic
diaryliodonium salts has been developed. A variety of Hydrocarbon; triphenylene; Diaryliodonium Salt
polycyclic aromatic hydrocarbons can be synthesized
efficiently according to this approach, such as triphenylene,
dibenzo[fg,op]tetracene, and tribenzo[fg,ij,rst]pentaphene
derivatives.
another efficient bay-region APEX reaction.[7]
Introduction
However, the synthesis of bay-region-halogenated
arenes needs multiple steps. In 2018, our group
developed a bay-region APEX reaction of electron-
Polycyclic aromatic hydrocarbons (PAHs) have
attracted substantial interest due to their potential
applications in organic optoelectronic materials.
[8]
rich biphenyls with diaryliodonium salts. A variety
of unsymmetrical triphenylenes could be synthesized
according to this method. However, the substrates
were limited to electron-rich biphenyls bearing 3,4-
dialkoxy groups which directed bay-region selectivity
by electron effect. Therefore, some new strategies for
directing bay-region selectivity are highly anticipated
to expand the substrate scope of biphenyls.
[
1]
Development of efficient synthetic methods for novel
PAHs is highly demanded in the fields of both
chemistry and materials.[ In recent years, the
annulative π-extension (APEX) of simple aromatic
hydrocarbons provides an efficient synthetic
approach for PAHs on account of the atom- and step-
economy.[ In earlier years, Itami and co-workers
reported the K-region two-step APEX reactions of
PAHs through sequential C−H arylation with o-
2]
3]
[4]
biphenylboroxins and Scholl cyclization. A few
years afterwards their group achieved the one-step
APEX reactions of PAHs by utilization of
dibenzosilole derivatives, diiodobiaryls as π-
[5]
extending reagents, respectively.
Although K-
region APEX reactions have been well developed,
bay-region APEX reactions remains a challenge due
to poor reactivity and regioselectivity. Focusing on
the diene-like character of the bay-region of PAHs,
researchers achieved Diels-Alder-type bay-region
APEX reactions of PAHs with various dienophiles
[
6a-6c]
[6c-6g]
[6h-6k]
such as alkenes,
alkynes,
arynes,
and
quinones.[ However, this type of bay-region APEX
reaction is applicable only to perylene, bistanthene,
benzoperylene, and their derivatives. Moreover,
dimerization of bay-region-halogenated arenes is
6l]
Scheme 1. Bay-region Two-Step APEX reactions of
biphenyls and terphenyls with diaryliodonium salts.
1
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Advanced Synthesis & Catalysis
10.1002/adsc.201901010
In 2009, Gaunt and co-worker developed a copper-
shown in entry 7, the best yield of 70% was obtained
provided that the temperature of arylation reaction
was reduced to 60 °C. However, further lowering the
temperature to 40 °C led to a significant reduction in
yield of 3aa to 20% (Table 1, entry 8). Screening of
catalyzed meta-selective C–H arylation reaction of
acylanilides.[ Their excellent work stimulates us to
explore the application of it in APEX reactions.
Herein, we report an amide-directed bay-region two-
step APEX reaction of biphenyls and terphenyls with
diaryliodonium salts (Scheme 1). A variety of PAHs
can be synthesized according to this approach, such
9]
copper catalysts indicated Cu(OTf)
all other tested copper salts (Table 1, entries 7, 9-12).
CHCl or CH Cl was used as the solvent instead of
2
was superior to
3
2
2
as triphenylene,[
10]
dibenzo[fg,op]tetracene,
[11]
and
DCE to result in low yields of 48%, 25% respectively
(Table 1, entries 13 and 14). In addition, lower
loading of catalyst led to a lower yield of 3aa (Table
tribenzo[fg,ij,rst]pentaphene derivatives.
1
, entry 15). No desired product 3aa was observed in
Results and Discussion
the absence of a copper catalyst (Table 1, entry 16).
Table 1. Optimization of reaction conditions.[a]
We began to investigate the amide-directed bay-
region two-step APEX reaction by using 4-
benzoylamino-3,4'-dimethyl-1,1'-biphenyl 1a and
3
,4-dimethoxyphenyl(mesityl)iodonium
tetrafluoroborate 2a as the model substrates (Scheme
). Initially, according to our previous reaction
2
[8]
condition, the APEX reaction of 1a was carried out
by use of 3.0 equivalents of 2a as a π-extending
reagent as well as an oxidant, Cu(OTf) as a catalyst,
2
and DCE as the solvent under argon. As a result, the
triphenylene derivative 3aa was obtained in a very
low yield of 9%. However, in the meanwhile, we
isolated the arylation product 3'aa in a high yield of
6
9%, which implied an additional oxidant was
needed to promote the Scholl cyclization.
[
a]
Reaction conditions: 1a (0.2 mmol), 2a (see table),
Cu(OTf) (0.02 mmol), DCE (2.0 mL), T (see table), t
48 h), FeCl (see table, 2.0 M in MeNO ), T (35 C), t (1
h), under argon. The yields are of isolated products.
2
1
1
(
3
2
2
2
b]
[
T
2
[
c]
[d]
(
90 C). CHCl
3 2 2
was used as the solvent. CH Cl was
used as the solvent.
Scheme 2. Preliminary attempt at bay-region two-step
APEX
diaryliodonium salts.
reaction
of
4-acylamino-biphenyls
with
With the optimized conditions in hand, we next
investigated the substrate scope of 4-acylamino-1,1'-
biphenyls 1. As summarized in Table 2, a variety of
4
-acylamino-1,1'-biphenyls with both electron-
Subsequently, we decided to perform the APEX
donating groups and electron-withdrawing groups
could undergo the bay-region APEX reaction to get
the triphenylene derivatives 3 in moderate to good
yields (25−70%). 4-Benzoylamino-1,1'-biphenyls
bearing electron-donating groups, such as methyl and
methoxy substituents, were compatible for obtaining
the corresponding products (3aa-3ga). It had a little
effect on the yields whether the methyl and methoxy
were 3-position, 3'-position or 4'-position. However,
the yield decreased significantly when the methyl was
2-position (3ca). 4-Benzoylamino-1,1'-biphenyls
bearing halogen substituents, such as Cl, or F, were
reaction of 1a using 2.0 equivalents of 2a as a π-
[12]
extending reagent and FeCl
3
as an additional
oxidant (Table 1). To our delight, the target product
aa was acquired in 32% yield (Table 1, entry 1).
When the cyclization temperature was reduced to
3
3
1
6
5 °C, the yield of 3aa was increased to 54% (Table
, entry 2). It was pleasing that the yield was raised to
3% when the amount of 2a was reduced to 1.5
equivalents, (Table 1, entry 3). An attempt to increase
the amount of FeCl to 5.0 equivalents resulted in a
slightly improved yield of 3aa (Table 1, entry 5). As
3
2
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Advanced Synthesis & Catalysis
10.1002/adsc.201901010
Table 3. Substrate scope of aryl(mesityl)iodonium salts.[a]
workable, whether the fluoro group was 4’-position,
3
-position or 2-position, and the corresponding
products were received in acceptable to good yields
3ha-3ka).
(
Table 2. Substrate scope of 4-benzoylamino-1,1'-
biphenyls.[
a]
[
a]
Reaction conditions: 1g (0.2 mmol), 2 (0.3 mmol),
Cu(OTf) (0.02 mmol), DCE (2.0 mL), T (60 C), t (48
h), FeCl (1.0 mmol, 2.0 M in MeNO ), T (35 C), t (1 h),
under argon. The yields are of isolated products.
2
1
1
3
2
2
2
[
b]
T
2
(30
[
c]

C). The data in parentheses are the ratio of isomers. The
1
ratios were determined by H NMR (3gc: 11-methyl/9-
methyl; 3ge: 10,11-dimethyl/9,10-dimethyl; 3pi: 10,11-
dichloro/9,10-dichloro; 3pj: 10,11-difluoro/9,10-difluoro).
[
d]
[e]
Aryl(mesityl)iodonium triflates were used.
pivaloylaminobiphenyls were used; T (80 C), T
4-
(50 C).
1
2
[
f]
T
1
(80 C), T (60 C).
2
Regrettably, 4-benzoylamino-1,1'-biphenyl 1l bearing
[
a]
strong electron-withdrawing group, such as CF could
Reaction conditions: 1 (0.2 mmol), 2a (0.3 mmol),
Cu(OTf) (0.02 mmol), DCE (2.0 mL), T (60 C), t (48
h), FeCl (1.0 mmol, 2.0 M in MeNO ), T (35 C), t (1 h),
1
under argon. The yields are of isolated products. T (70
3
not undergo this transformation to get the
corresponding product (3la). 4-Benzoylamino-1,1'-
biphenyl 1m was also a good substrate for this
transformation to deliver the product 3ma in a yield
2
1
1
3
2
2
2
[
b]
[
c]

C), T
2
(45 C).
T
1
(80 C), T (35 C).
2
3
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Advanced Synthesis & Catalysis
10.1002/adsc.201901010
of 51% (3ma). In addition, the substrates containing
different directing groups were also examined. The
results indicated that use of 4-pivalylamino-1,1'-
biphenyl 1n as a substrate generated the product 3na
in a good yield of 68% (3na). However, 4-
acetylamino-1,1'-biphenyl 1o was employed to yield
the product 3oa in a low yield of 25% (3oa).
We were pleased to find that dual APEX reactions
of 4-benzoylamino-1,1'-biphenyls proceeded to
generate dibenzo[fg,op]tetracene derivatives 4 when
unsubstituted 4-benzoylamino-1,1'-biphenyls at 3-
position were utilized as substrates (Table 4). Using
(3,4-dimethoxyphenyl)(mesityl)iodonium
tetrafluoroborate 2a as a π-extending reagent, various
4'-substituted 4-benzoylamino-1,1'-biphenyls with
methyl, methoxy, ethoxy or hydrogen could undergo
the dual APEX reaction to provide the corresponding
products 4 in acceptable yields (4qa-4ta). (2,3-
Dihydrobenzo[β][1,4]dioxin-6-yl)(mesityl)iodonium
tetrafluoroborate 2m reacted with 4-benzoylamino-4'-
methyl-1,1'-biphenyl 1q to deliver the anticipated
product 4qm in a moderate yield (4qm).
To explore the substrate scope of diaryliodonium
salts 2, 4-acylamino-1,1'-biphenyl 1g was employed
as the partner (Table 3). The results indicated that a
variety of aryl(mesityl)iodonium salts substituted on
the aromatic rings with alkyls, alkoxys, halogens or
COOMe group could undergo this transformation to
give the desired triphenylene derivatives 3 in
acceptable to good yields (22−64%). When
aryl(mesityl)iodonium salts bearing methyl, tert-butyl
or methoxy substituents, were selected as the π-
extending reagent, the APEX reaction proceeded
smoothly to generate the corresponding products in
Table 5. Synthesis of tribenzo[fg,ij,rst]pentaphene
[
a]
derivatives.
moderate
to
good
yields
(3gb-3gg).
phenyl(mesityl)iodonium salt 2h was also a good
substrate for this transformation (3gh). It is notable
that aryl(mesityl)iodonium salts with two halogen
substituents were also compatible to this reaction to
afford the desired products in acceptable yields (3pi
and 3pj). In addition, the aryl(mesityl)iodonium salt
2
k bearing COOMe group could also generate the
target product 3gk in a yield of 22%. Unfortunately,
the aryl(mesityl)iodonium salt 2l bearing CN group
could not undergo this transformation to get the
desired product 3gl. It is noteworthy that the isomers
had been observed when aryl(mesityl)iodonium salts
2
c, 2e, 2i and 2j were used as the π-extending
reagents (2gc, 2ge, 2pi and 2pj). The ratios of
isomers were listed in parentheses in Table 3.
Table 4. Synthesis of dibenzo[fg,op]tetracene derivatives.[a]
[
a]
Reaction conditions: 1 (0.1 mmol), 2m (0.5 mmol),
Cu(OTf)
2
(0.03 mmol), CHCl
2
CHCl
2
(1.0 mL), T
), T
2
1
(80 C),
(40 C),
t
t
1
(60 h), FeCl (1.0 mmol, 2.0 M in MeNO
(45 min.), under argon. The yields are of isolated
3
2
2
[
b]
products.
1
T (110 C).
In addition, the multiple APEX reactions of 4,4''-
dipivaloylamino-1,1':4',1''-terphenyls were also
explored. As shown in Table 5, both 3,3''-dimethyl-
,4''-dipivaloylamino-1,1':4',1''-terphenyl 1u and 3,3''-
4
dimethoxy-4,4''-dipivaloylamino-1,1':4',1''-terphenyl
1
v could react with (2,3-Dihydrobenzo[β][1,4]dioxin-
6
-yl)(mesityl)iodonium tetrafluoroborate 2m to
generate the desired tribenzo[fg,ij,rst]pentaphene
derivatives 5um and 5vm.
[
a]
Reaction conditions: 1 (0.1 mmol), 2 (0.4 mmol),
Cu(OTf) (0.03 mmol), CH Cl (1.0 mL), T (40 C), t (60
h), FeCl (1.0 mmol, 2.0 M in MeNO ), T (see table), t
see table), under argon. The yields are of isolated products.
2
2
2
1
1
3
2
2
2
Conclusion
(
4
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Advanced Synthesis & Catalysis
10.1002/adsc.201901010
Cu(OTf)
2
(10.8 mg, 0.03 mmol), substituted 4-acylamino-
In summary, we have developed an amide-directed
bay-region two-step annulative π-extension reaction
of biphenyls and terphenyls with diaryliodonium salts.
A variety of polycyclic aromatic hydrocarbons can be
synthesized according to this approach, such as
1
,1'-biphenyls 1 (0.1 mmol) and diaryliodonium salts 2
(
0.4 mmol) were placed into a 25 mL Schlenk tube
equipped with a magnetic stir bar. To this mixture was
added dry CH Cl (1.0 mL) with an injection syringe under
2
2
argon atmosphere. The reaction mixture was stirred for 60
h at 40 °C. Then the reaction mixture was cooled to room
temperature, quenched by the addition of 10 mL water, and
extracted with dichloromethane (3 × 10 mL). The
combined organic layer was washed with saturated
triphenylene,
dibenzo[fg,op]tetracene
and
tribenzo[fg,ij,rst]pentaphene derivatives. Rapid and
efficient access to various polycyclic aromatic
hydrocarbons represents the most attractive
advantage of this approach. Further studies on
efficient synthesis for polycyclic aromatic
hydrocarbons by the bay-region annulative π-
extension reactions are now underway in our
laboratory.
aqueous solution of NaHCO
over anhydrous MgSO , and concentrated in vacuum. The
residue was purified by column chromatography on silica
gel (eluent: petroleum ether ethyl acetate
dichloromethane = 3 : 1 : 2) to afford the products 4'.
3
and brine in sequence, dried
4
/
/
The compounds 4' (0.1 mmol) were placed into a 25 mL
Schlenk tube equipped with a magnetic stir bar. To this
2 2 3
tube was added CH Cl (4.5 mL), FeCl (1.0 mmol, 2.0 M
2
in MeNO ) in sequence with an injection syringe under
argon atmosphere. The mixture was stirred for appointed
time at the appointed temperature (see Table 4). Then the
reaction mixture was quenched by the addition of 10 mL
water, and extracted with dichloromethane (3 × 10 mL).
The combined organic layer was dried over anhydrous
Experimental Section
General remarks
1
All manipulations were conducted with Schlenk tube. H
4
MgSO , and concentrated in vacuum. The residue was
NMR spectra were recorded on the Varian 400 MHz or
Bruker 600 MHz spectrometers. Chemical shifts (in ppm)
were referenced to tetramethylsilane (δ = 0 ppm) as an
purified by column chromatography on silica gel (eluent:
petroleum ether / ethyl acetate / dichloromethane = 1 : 1 :
1) to afford the products 4.
13
internal standard in CDCl
3
, DMSO-d
6
or C
2
D
2
Cl4.
C
NMR spectra were obtained by the same NMR
General
procedure
for
synthesis
of
spectrometers and calibrated with CDCl
DMSO-d (δ = 39.43 ppm) or C Cl
3
(δ = 77.00 ppm),
(δ = 73.78 ppm).
tribenzo[fg,ij,rst]pentaphene 5
6
2
D
2
4
High-resolution mass spectra (HRMS) were obtained using
electrospray ionization (ESI) mass spectrometer or matrix
assisted laser desorption ionization (MALDI) mass
spectrometer. Melting points were determined with a
Cu(OTf)
2
(10.8 mg, 0.03 mmol), substituted 4,4''-
diacylamino-1,1':4',1''-terphenyls
1
(0.1 mmol) and
diaryliodonium salts 2 (0.5 mmol) were placed into a 25
mL Schlenk tube equipped with a magnetic stir bar. To this
melting point apparatus. The dry DCE and CH
2
Cl
2
. DCE containing 0.1% v/v H O
2
were
2 2
mixture was added CHCl CHCl with an injection syringe
freshly distilled over CaH
2
under argon atmosphere. The reaction mixture was stirred
for 60 h at appointed temperature (see Table 5). Then the
reaction mixture was cooled to room temperature,
quenched by the addition of 10 mL water, and extracted
with dichloromethane (3 × 10 mL). The combined organic
layer was washed with saturated aqueous solution of
was preparated from dry DCE and the distilled water.
Unless otherwise noted, other materials obtained from
commercial suppliers were used without further
purification. Substituted biphenyls or terphenyls 1 were
synthesized via suzuki coupling according to literature
[
13]
method.
diaryliodonium tetrafluoroborates 2a, 2b, 2c,
NaHCO
MgSO
3
and brine in sequence, dried over anhydrous
2
d, 2f, 2h and 2m were synthesized from arylboronic acid,
4
, and concentrated in vacuum. The residue was
2
-(diacetoxyiodo)mesitylene and BF
3
·Et
2
O according to
[
14]
purified by column chromatography on silica gel (eluent:
petroleum ether / ethyl acetate / dichloromethane = 4 : 1 :
literature methods.
Diaryliodonium triflates 2e, 2g, 2i,
2
j, 2k and 2l were synthesized from iodoarene, mesitylene
2
) to afford the products 5'.
and trifluoromethanesulfonic acid using m-CPBA as an
[
15]
oxidant according to literature methods.
The compounds 5' (0.1 mmol) were placed into a 25 mL
Schlenk tube equipped with a magnetic stir bar. To this
General procedure for synthesis of triphenylenes 3
2 2 3
tube was added CH Cl (4.5 mL), FeCl (1.0 mmol, 2.0 M
2
in MeNO ) in sequence with an injection syringe under
Cu(OTf)
,1'-biphenyls 1 (0.2 mmol) and diaryliodonium salts 2
0.3 mmol) were placed into a 25 mL Schlenk tube
equipped with a magnetic stir bar. To this mixture was
2
(7.2 mg, 0.02 mmol), substituted 4-acylamino-
argon atmosphere. The mixture was stirred for appointed
time at the appointed temperature (see Table 5). Then the
reaction mixture was quenched by the addition of 10 mL
water, and extracted with dichloromethane (3 × 10 mL).
The combined organic layer was dried over anhydrous
1
(
2
added DCE (2.0 mL, contains 0.1% v/v H O) with an
injection syringe under argon atmosphere. The reaction
mixture was stirred for 48 h at the appointed temperature
4
MgSO , and concentrated in vacuum. The residue was
purified by column chromatography on silica gel (eluent:
ethyl acetate / dichloromethane = 1 : 2) to afford the
products 5.
(
see Table 2 and Table 3). Then the reaction mixture was
3 2
cooled to 35 °C, and FeCl (1.0 mmol, 2.0 M in MeNO )
was added with an injection syringe under argon
atmosphere. The mixture was stirred for additional 1 h at
3
5 °C. Then the reaction mixture was quenched by the
addition of 10 mL water, and extracted with Acknowledgements
dichloromethane (3 × 10 mL). The combined organic layer
was washed with saturated aqueous solution of NaHCO
3
We are grateful for the financial supports from National Natural
Science Foundation of China (Nos. 21871195 and 21772135),
and Sichuan Normal University.
4
and brine in sequence, dried over anhydrous MgSO , and
concentrated in vacuum. The residue was purified by
column chromatography on silica gel (eluent: petroleum
ether / ethyl acetate / dichloromethane = 5 : 1 : 2) to afford
the products 3.
References
General
procedure
for
synthesis
of
dibenzo[fg,op]tetracenes 4
[
1] For selected reviews, see: a) Polycyclic Arenes and
Heteroarenes: Synthesis, Properties, and Applications;
5
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Advanced Synthesis & Catalysis
10.1002/adsc.201901010
Q. Miao, Ed.; Wiley-VCH: Weinheim, 2016; b)
D. Wang, Y. Zhao, W.-Y. Sun, Z. Shi, Angew. Chem.
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[
2] For the reviews, see: a) R. G. Harvey, Curr. Org. Chem.
2
004, 8, 303-323; b) B. P. Mathew, M. R. Kuram,
Inorg. Chim. Acta 2019, 490, 112-129.
[
[
9] R. J. Phipps, M. J. Gaunt, Science 2009, 323, 1593-
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Angew. Chem. Int. Ed. 2017, 56, 11144-11164; Angew.
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K. Murakami, K. Itami, J. Am. Chem. Soc. 2019, 141,
1597.
10] For the synthesis of triphenylenes by palladium-
catalyzed amide-directed one-step APEX reaction of
benzene derivatives with cyclic diaryliodonium salts,
see: a) B. P. Mathew, H. J. Yang, J. Kim, J. B. Lee, Y.-
T. Kim, S. Lee, C. Y. Lee, W. Choe, K. Myung, J.-U.
Park, S. Y. Hong, Angew. Chem. Int. Ed. 2017, 56,
5007-5011; Angew. Chem. 2017, 129, 5089-5093; For
the synthesis of triphenylenes by palladium-catalyzed
non-directed one-step APEX reaction of benzene
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Advanced Synthesis & Catalysis
10.1002/adsc.201901010
FULL PAPER
Amide-Directed Bay-Region Two-Step Annulative
π-Extension (APEX) of Biphenyls and Terphenyls
with Diaryliodonium Salts: Efficient Access to
Polycyclic Aromatic Hydrocarbons
Adv. Synth. Catal. Year, Volume, Page – Page
Q. Peng, W. Zhang, K. Zhao, Y. Du, C. Feng, B.-
Q. Wang, D.-M. Fang, X.-Z. Chen, H.-L. Ni,* and
S.-K. Xiang*
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