Selectivity-switchable construction of benzo-fused polycyclic compounds through a gold-catalyzed reaction of enyne-lactone

Article abstract of DOI:10.1039/c7cc09786g

A gold-catalyzed selectivity-switchable reaction of enyne-lactone is reported. Different products, including naphthalenes and benzo-fused polycyclic compounds, can be selectively obtained from the same starting material. The choice of the gold complex is the key for the chemoselectivity of this system.

Full text of DOI:10.1039/c7cc09786g

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DOI: 10.1039/C7CC09786G
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COMMUNICATION
Selectivity-switchable construction of benzo-fused polycyclic
compounds through a gold-catalyzed reaction of enyne-lactone
Kui Luo,a Ling Zhang,a Huanfeng Jiang,a Lianfen Chen,*a and Shifa Zhu*ab
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
www.rsc.org/
A gold-catalyzed selectivity-switchable reaction of enyne-lactone
is reported. Different products, including naphthalenes and benzo-
fused polycyclic compounds, can be selectively obtained from the
same starting material. The choice of gold complex is the key for
the chemoselectivity of this system.
OMe
MeO2C
O
O
Me
CO2
Ar
OMe
Ar
O
a
[M]
[M]'
O
b
a
E
b
path
path
Ar
2
3
1
work
work
Previous
This
E
O
Chemoselectivity remains a long-standing challenge in the
development of organic synthetic methodology and total
synthesis, and constant efforts have been made by researchers
to address this issue.1 Currently, different strategies have been
established to realize high chemoselectivity, for instance, by
modulating the substrate structure2 or changing the reaction
conditions,3 including variation of catalysts,4,5 ligands,6,7
solvents7 and so on. Controlling the reaction chemoselectivity
could result in selective formation of two or more different
products from the same starting material. As part of our
continuous efforts to develop highly efficient tandem reactions
based on alkyne chemistry,8 we are interested in how to
achieve effective control of chemoselectivity as well.
O
Me
O
OMe
9
O
E
O
Ar
[M]
=
[M]'
E
Me
CO2
Ar
II
I
Scheme 1 Gold-catalyzed reaction of enyne-lactone
would be a challenge. In this work, we would like to report the
chemoselective construction of polycyclic compounds from
enyne-lactone by tuning the reaction conditions.
3
1
In our previous work,9 under the optimized reaction
conditions (Table 1, entry 1), the naphthyl ester product 2a
could be obtained in 74% yield with Ph3PAuCl/AgSbF6 as
catalyst, accompanied by trace amount of product 3a. When
AgBF4 was applied as the halogen scavenger instead of AgSbF6,
the desired product 3a could be detected in 6% yield (Table 1,
entry 2). In addition to Ph3PAu+, different nitrogen heterocyclic
carbene (NHC) ligated gold complexes (NHC-AuCl) were
utilized as catalysts as well. The results showed that both
IMesAu+ and SIMesAu+ complexes were ineffective for this
catalytic reaction (Table 1, entries 3 and 4). To our delight, the
yield of 3a could be improved to 42% in the presence of
IPrAuCl/AgBF4, accompanied by 2a in 58% yield (Table 1, entry
5). Changing the gold complex IPrAuCl to SIPrAuCl, the yield of
3a could be further improved to 50% (Table 1, entry 6). The
variations of silver salts could not further increase the reaction
yield (Table 1, entries 7-9). Gratifyingly, the yield could be
enhanced to 70% when the reaction temperature was raised
Recently, we reported a gold-catalyzed ring-expansion of
enyne-lactone
derivatives
condition screening, polycyclic product
a minor side product, which aroused our great interest due to
its unique structure. Obviously, the generation of product
1
to selectively synthesize naphthalene
(Scheme 1, path a).9 During the reaction
was also detected as
2
3
3
should come from a tandem of 5-exo-dig cyclization and
intramolecular Friedel-Crafts reaction (Scheme 1, path b).10-11
Due to the greater steric hindrance caused by the ester group
of path b, how to selectively produce the desired product
3
a
Key Laboratory of Functional Molecular Engineering of Guangdong Province,
School of Chemistry and Chemical Engineering, South China University of
Technology, Guangzhou, 510640, P. R. China.
o
to 100 C (Table 1, entry 10). In this case, the naphthalene 2a
b State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin
300071, P. R. China
was suppressed to only 13% yield. Lower temperature
decreased both the reaction conversion and the
selectivity(Table 1, entry 11). AgBF4 alone gave the products 2a
E-mail: zhusf@scut.edu.cn, chenlf@scut.edu.cn
†
Electronic supplementary information (ESI) available: Spectroscopy details. CCDC
1586574, 1586587 and 1526307. For ESI and crystallographic data in CIF or other
electronic format see DOI: 10.1039/x0xx00000x
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 1
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Table 1 Optimization of the reaction conditionsa
OMe
O
View Article Online
MeO2C
O
mol
SIPrAuCl
%)
O
(5
mol
DOI: 10.1039/C7CC09786G
OMe
OMe
MeO2C
%)
AgBF
4 (5
O
OMe
O
Ar2
O
Me
O
DCE, 100 o
N
Ar1
CO2
Ph
E
Ar2
Cat.
C,
2
O
Ar1
T
Sol.,
1
3
E
O
E
O
O
O
O
O
Ph
OMe
OMe
OMe
1a
2a
3a
Me
Et
E
E
Yieldb (%)
3a
(70%)
scale
3b 75%)
3c
Entry
Cat.
Add.
T (oC)
2a
3a
(
(72%)
O
b
gram
(67%,
)
O
O
O
O
O
OMe
OMe
OMe
1
2
3
Ph3PAuCl
Ph3PAuCl
IMesAuCl
AgSbF6
AgBF4
AgBF4
80
80
74
40
Trace
6
tBu
E
E
E
80
80
80
80
80
80
80
100
60
Trace
Trace
58
22
26
Trace
41
13
41
7
Trace
Trace
42
50
39
Me
(71%)
O
MeO
3f 63%)
(
4
5
6
7
8
9
10
11
12
13
SIMesAuCl AgBF4
3d
71%)
O
3e
(
O
IPrAuCl
AgBF4
AgBF4
AgSbF6
AgNTf2
AgOTf
AgBF4
AgBF4
AgBF4
OMe
Me
OMe
Me
O
O
O
OMe
SIPrAuCl
SIPrAuCl
SIPrAuCl
SIPrAuCl
SIPrAuCl
SIPrAuCl
E
E
E
Me
Me
Trace
31
+
=
3h/3h' 55/45)
3h 3h'
3g (67%)
(85%,
O
O
O
O
OMe
=
=
=
X
X
X
3-F
70c
18
OMe
3j
(53%)
2
3k
3-Cl
3-Br
3m X 5-Cl
1
(55%)
(52%)
(60%)
OMe
NO2
3
E
3l
E
X
=
6
4
100
100
12
NR
5
3i 78%)
(
O
O
O
NR
O
O
O
OMe
O
OMe
OMe
a Unless otherwise noted, the reaction was performed with 1a (0.2
mmol) in DCE (2 mL), 12 h, under N2, E = CO2Me. b The yield was
determined by 1H NMR using 1-methyl-4-nitrobenzene as an
internal standard. c Isolated yield.
E
E
E
O
O
N
O
nr
3o
nr
3n trace
3p
O
O
O
OMe
OMe
OMe
E
E
E
MeO
MeO
MeO
and 3a in only 7% and 12% yield, respectively (Table 1, entry 12).
Furthermore, the reaction did not occur at all without the catalyst
and additive (Table 1, entry 13). Several other Lewis acids were also
tested, showing unsatisfactory performances (see the Electronic
supplementary information for more details).
Me
3q
3t
3r
3s
(70%)
(91%)
O
OMe
(70%)
O
OMe
O
O
O
O
OMe
OMe
E
E
F
E
O
With the optimized reaction conditions (Table 1, entry 10) in
hand, the substrate scope was then examined. As shown in Scheme
2, this catalytic system could be successfully extended to a variety
of aryl enyne-lactones 1. Various derivatives of 1 tethered with aryl
groups on the distal alkyne could serve as effective substrates,
producing the desired products 3b-m in 52-78% yields. The reaction
results revealed that the substrates with an electron-rich aryl group
(3b-i) functioned better than those with electron-poor aryl group
(3j-m). Furthermore, the reaction did not take place when a nitro
group was introduced to the Ar1 group (3n). These results were well
consistent with the proposed Friedel-Crafts reaction mechanism.
The structure of products 3a and 3l were verified by X-ray
crystallography analysis (see the ESI†). It is noted that no reaction
occurred with enyne-lactone containing a 2-pyridyl terminal group
under the standard conditions (see 3o), which could probably be
attributed to the strong coordination of pyridine to the cationic Au
center, thus inhibiting the catalyst turnover. The enyne-lactones 1
tethered with furan group on the distal alkyne was ineffective for
this transformation either (see 3p). For the enyne-lactone with a
meta-substituted Ar1 group, a mixture of isomers could be obtained
(see 3h and 3h’). Furthermore, the substrates bearing different
fused arylene rings (Ar2) were also tested. The substrates with
electron-donating arylene (3q-t, 70- 91%) proceeded much
O
F
3u
3v
(72%)
O
(45%)
O
(53%)
O
OMe
O
O
O
OMe
S
E
E
E
Cl
Cl
nr
3w
3x
3y
(61%)
(65%)
a
Scheme 2 Reaction scope for the formation of
3.
Reaction
conditions:
1
(0.2 mmol), SIPrAuCl (5 mol%) and AgBF4 (5 mol%)
o
in DCE (2 mL) at 100 C under N2 for 12 h, isolated yield, E =
CO2Me. 1a (3.03 mmol, 1.05 g), SIPrAuCl (7.5 mol %) and
AgBF4 (7.5 mol %).
b
better than those with electron-withdrawing arylene (3u-x, 45-
65%). The thienyl-tethered enyne-lactone, which was effective
in our previous Ph3PAu+-catalyzed system,9 was not
compatible with this catalytic system (3y), probably due to the
stronger coordination of sulphur atom in thienyl moiety to the
softer gold center of the SIPrAu+ catalyst, which then entirely
retarded the reaction. What’s more, the reaction proceeded
smoothly on a gram scale, leading to the corresponding
product 3a in good yield (67%).
In order to further explore the substrate scope, the enyne-
lactones with a simple C=C double bond rather than the fused
arylene ring were also subjected to the reaction under the
2 | J. Name., 2012, 00, 1-3
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A tentative reaction mechanism for the formation of
3
OR1
View Article Online
R2O2C
R3
O
under the gold-catalyzed conditions wasDpOroI:p10o.s10e3d9/inC7SCcCh0e9m78e6G5.
mol
SIPrAuCl
%)
%)
O
(5
mol
OR1
Ar
O
AgBF4 (5
O
Taking substrate 1a as an example, the triple bond of enyne-
lactone was initially activated by gold salt to give the
intermediate A, followed by 5-exo-dig cyclization and
intramolecular Friedel-Crafts reaction to give the desired
R3
E
DCE, 100 o
N
2
C,
R4
O
R4
Ar
3
1
O
O
E
O
O
O
O
O
O
OMe
OEt
OMe
product 3a
.
Me
Me
E
Me
E
Me
O
O
O
O
b
3aa
3ab
3ac
(65%)
O
(63%)
(70%)
OMe
OMe
OMe
O
O
Me
E
E
O
OMe
OMe
Ph
[Au]
[Au]
O
E
Me
E
Me
E
B
C
O
O
E
O
OMe
Me
OMe
reaction
5-exo-dig/Friedle-Crafts
H
3ad
3ae
3af
(57%)
CO2
(62%)
(55%)
O
O
tBu
MeO
Me
Cl
Ph
[Au]
[Au]
O
OMe
OMe
D
A
Cl
Me
E
E
[Au]
OMe
O
O
MeO2C
O
OMe
Me
3ag
Me
3ah
(46%)
(61%)
O
E
=
E
CO2Me
3a
Ph
1a
Scheme 3 Reaction scope for the formation of
was conducted in DCE at 100 oC for 12 h using 5 mol %
SIPrAuCl and 5 mol % AgBF4 under N2, enyne-lactones (0.2
mmol), DCE (2 mL), isolated yield, E = CO2Me. b E = CO2Et.
3.
a The reaction
Scheme 5 The proposed reaction mechanism.
1
In conclusion, we have reported an efficient gold-catalyzed
standard conditions. As summarized in Scheme 3, the catalytic reaction of enyne-lactone to selectively afford the benzo-fused
process could be successfully applied to different kinds of polycyclic compounds. This reaction was proposed through a
substrates as well, obtaining the desired products 3aa-ah in consecutive 5-exo-dig cyclization and Friedel-Crafts reaction. The
46-70% yields. The structure and stereochemistry of the choice of gold complex is the key for the selectivity of this reaction.
product was also confirmed by the X-ray diffraction analysis of With the combination of Ph3PAuCl/AgSbF6 as the catalyst, the
compound 3aa (see the ESI
With the products
†
for detail).
reaction preferred the O-attack reaction pathway (Scheme 1, path
3
in hand, two further chemical a). However, when it came to the combination of SIPrAuCl/AgBF4,
transformations were carried out (Scheme 4). Taking 3a as an the reaction selectivity was switched to C=C double bond-attack
example, the carbon-carbon double bond could be selectively pathway (Scheme 1, path b). The chemoselectivity might be
reduced to carbon-carbon single bond under Pd/C-H2 derived from the differences of electron population in the
condition at room temperature, furnishing the desired product alkyne activated by gold catalysts. The SIPr ligated gold center
4
in 70% yield (Scheme 4, eq. 1). Furthermore, the ester group might have more electron density owing to its strong σ-donor
of 3a could be removed with LiBr·H2O in DMSO at 140 °C, and and weak π-acceptor properties, making the alkyne less
the desired product
eq. 2).
5
was generated in 63% yield (Scheme 4, electron-deficient, which might favour the soft vinyl ether
addition. While the Ph3PAuCl could make the alkyne more
electron-deficient and favourable for the hard oxygen attack.
In addition, the steric hindrance differences between SIPrAuCl
and Ph3PAuCl might be another contributor to affect the
O
O
OMe
H2 Pd/C
,
O
regioselectivity. The advantages of broad substrate scope and
tunable selectivity make this system very appealing for the
synthesis of different benzo-fused polycyclic compounds.
E
(1)
(2)
O
rt, 4 h
MeOH,
OMe
70%
4
E
O
O
OMe
3a
LiBr H
2O
We are grateful to Ministry of Science and Technology of
the People’s Republic of China (2016YFA0602900), the NSFC
(21372086, 21422204, and 21672071), Guangdong NSF
(2014A030313229, 2016A030310433), the Science and
Technology Program of Guangzhou (201707010316), and the
Fundamental Research Funds for the Central Universities,
SCUT.
h
DMSO, 140 °C, 8
63%
5
Scheme 4 Further transformations of 3a. Reaction conditions: (1) 3a
(0.2 mmol), Pd/C (watted with ca. 55 % water) (20 MW %), H2 (1
atm), MeOH (2 mL); (2) 3a (0.2 mmol), LiBr‧ H2O (0.4 mmol), DMSO
(2 mL). Note: E = CO2Me.
Notes and references
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DOI: 10.1039/C7CC09786G
A gold-catalyzed selectivity-switchable reaction of enyne-lactone is reported. The choice of gold
complex is the key for the chemoselectivity.