A metal-free addition/dearomatization-cyclization/decarboxylation cascade of aryl 3-arylpropiolate toward the synthesis of 1,1-diaryl-2-alkyl-substituted ethylenes

Article abstract of DOI:10.1016/j.tetlet.2016.02.013

A radical-participated addition/dearomatization-cyclization/decarboxylation cascade between aryl 3-arylpropiolate and ethers (cycloalkane) has been developed to give a series of 1,1,2-trisubstituted ethylenes in moderate to good yields.

Full text of DOI:10.1016/j.tetlet.2016.02.013

Tetrahedron Letters 57 (2016) 1239–1242
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Tetrahedron Letters
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A metal-free addition/dearomatization–cyclization/decarboxylation
cascade of aryl 3-arylpropiolate toward the synthesis of 1,1-diaryl-2-
alkyl-substituted ethylenes
a
a
a
a
a
a
a
Jie Wang , Xue-Qing Mou , Bang-Hong Zhang , Wei-Ting Liu , Chao Yang , Li Xu , Zheng-Liang Xu ,
a,b,
⇑
Shao-Hua Wang
a
School of Pharmacy & State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, PR China
Key Laboratory of Drug Targeting and Drug Delivery System, Ministry of Education, Sichuan University, Chengdu, PR China
b
a r t i c l e i n f o
a b s t r a c t
Article history:
A radical-participated addition/dearomatization–cyclization/decarboxylation cascade between aryl
Received 1 December 2015
Revised 29 January 2016
Accepted 3 February 2016
Available online 4 February 2016
3
-arylpropiolate and ethers (cycloalkane) has been developed to give a series of 1,1,2-trisubstituted
ethylenes in moderate to good yields.
Ó 2016 Elsevier Ltd. All rights reserved.
Keywords:
Tandem reaction
1
,1,2-Trisubstituted ethylenes
Aryl 3-arylpropiolate
Decarboxylation
The synthesis of multisubstituted alkenes is an evergreen topic
in the field of synthetic chemistry as these types of structural moi-
eties broadly exist in a number of bioactive molecules and impor-
tant synthetic intermediates such as Tamoxifen, Claravis, Tamiflu,
and Sutent (Fig. 1). Different from the synthesis of mono- or di-
substituted alkenes, whose synthetic methodologies have been
well established, developing new methods for the synthesis of
tri- or tetra-substituted alkenes is still far more underdeveloped
as there is lack of general methods for this problem.1 After years
of efforts of synthetic chemists, three common strategies, elimina-
tion from proper alkanes, addition to the alkynes, and substitution
of alkenes have been successfully applied to this subject. Espe-
cially, under the stimulation of the C–H functionalization, a num-
ber of methods for the construction of this type of moiety have
been developed through the direct functionalization of carbon–
carbon double/triple bond.2 Nevertheless, it is still desirable to
further investigate this topic.
corresponding studies have led to the construction of two major
types of molecular skeletons, that is, chroman-2-one and 1-oxas-
piro[4.5]deca-3,6,9-triene-2,8-dione (Scheme 1, Eqs. 1 and 2).6
As for the former one (Scheme 1, Eq. 1), produced from a better
studied reaction mode, a series of reagents have been successfully
applied to it under either transition metal catalysis or metal-free
,7
6
conditions. Different from the first reaction mode, the involve-
ment of an ipso-cyclization would afford the products with an
oxa-spiro skeleton through a dearomatization process (Scheme 1,
7
Eq. 2). Regarding to the second type of reaction, only limited num-
ber of reagents like tetrahydrofuran, the Langlois reagent, halo-
nium reagent, and bisiodonium salts were used in the
transformation. And most of them need the presence of a transition
metal catalyst. In connection with our interest in the difunctional-
8
ization reaction of carbon–carbon double or triple bond, our initial
,3
goal was to develop a metal-free version of the reaction between
aryl 3-arylpropiolate and 1,4-dioxane with the use of proper oxi-
dant. Different from what we expected, a trisubstituted alkene
In recent years, difunctionalization reactions of carbon–carbon
double/triple bond through an addition/cyclization cascade have
received considerable attention of organic chemistry commu-
2
was obtained in moderate yield when PhI(OAc) was used as the
oxidant for the reaction between phenyl 3-phenylpropiolate (1a)
and 1,4-dioxane (2a) (Scheme 1, Eq. 3). In our opinion, this trans-
formation represents a new reaction mode for this type of sub-
strate and might bring an alternative way for the synthesis of
4
–7
nity.
In particular, for those involving the activated carbon–
carbon triple bond of aryl 3-arylpropiolate type of substrate,
9
related alkenes. Herein, we present the results for this tandem
⇑
Corresponding author.
E-mail address: wangshh@lzu.edu.cn (S.-H. Wang).
http://dx.doi.org/10.1016/j.tetlet.2016.02.013
040-4039/Ó 2016 Elsevier Ltd. All rights reserved.
0

1
240
J. Wang et al. / Tetrahedron Letters 57 (2016) 1239–1242
NMe
2
Table 1
a
Optimization of reaction conditions
O
O
OH
Et
O
O
oxidant
+
Tamoxifen
Claravis
O
O
O
O
O
1a
2a
3a
t (h)
O
F
O
N
H
Entry
Oxidant (equiv)
PhI(OAc) (1.2)
DTBP (1.2)
(1.2)
(1.2)
Temp (°C)
Yieldb (%)
HN
O
N
HN
NH
2
N
H
1
2
3
4
5
6
7
8
9
2
80
80
80
80
80
80
80
60
12
12
12
12
12
12
12
12
12
12
12
1
2
5
3
2
2
2
2
2
34
27
n.d.
O
c
Tamiflu
Sutent
d
K
H
2
S
2
O
8
2
O
2
16
24
26
48
25
59
64
60
45
63
64
38
62
74
69
Figure 1. Selected molecules with multisubstituted double bond.
e
TBPB (1.2)
CHP (1.2)
f
BPO (1.2)
BPO (1.2)
BPO (1.2)
BPO (1.2)
BPO (1.2)
BPO (1.2)
BPO (1.2)
BPO (1.2)
BPO (0.5)
BPO (0.8)
BPO (1)
BPO (2)
—
reaction, in which an addition/dearomatization–cyclization/
decarboxylation cascade was involved.
90
1
1
1
0
1
2
100
110
100
100
100
100
100
100
100
100
100
100
100
After observing the initial result, we began the reaction condi-
tion optimization of this tandem transformation with phenyl 3-
phenylpropiolate (1a) and 1,4-dioxane (2a) as the mode substrates.
Accordingly, a series of oxidants were screened to promote this
reaction at 80 °C (Table 1, entries 1–7), and most of them could
afford the expected product 3a. Among them, the use of benzoyl
peroxide (BPO) could give the expected product 3a in the highest
yield of 48% (Table 1, entry 7), while no desired product could be
13
14
1
1
1
1
5
6
7
8
d
19
n.d.
g
h
i
20
21
22
BPO (1)
BPO (1)
BPO (1)
55
50
30
detected in the presence of K
reaction was carried out at different temperatures (Table 1, entries
–11), through which the yield of the product 3a was further
increased to 64% when the transformation was performed at
00 °C (Table 1, entry 10). Having the above results, we further
2 2 8
S O (Table 1, entry 3). Next, the
2
2
8
a
Reaction conditions: without other notifications, all the reactions were per-
formed with phenyl 3-phenylpropiolate (50 mg, 0.23 mmol) in 1,4-dioxane (1 mL)
under Ar.
1
optimized the reaction conditions by varying the amount of the
BPO (Table 1, entries 12–18). It was found that the best result
was obtained in the presence of 1 equiv of BPO (Table 1, entry
7). Increasing the amount of BPO did not give a clear improve-
ment of the reaction result (Table 1, entry 18), and the yield of
a was clearly decreased by reducing the amount of BPO (Table 1,
b
Isolated yield.
c
DTBP = di-tert-butyl peroxide.
d
n.d. = not detected.
e
TBPB = tert-butyl peroxybenzoate.
1
f
CHP = cumyl hydroperoxide.
g
The reaction was carried out under air.
,4-Dioxane (0.5 mL) was used.
1,4-Dioxane (0.25 mL) was used.
3
h
1
i
entries 15 and 16). Besides, it should be noted that carrying the
reaction for 2 h was enough to afford the best result (Table 1, entry
1
7), and no product 3a was obtained without the use of BPO
With the optimized reaction conditions in hand (Table 1, entry
7), we further evaluated the generality of this transformation. As
(Table 1, entry 19). The reaction was also performed under air or
1
with less amount of 1,4-dioxane, but all these attempts led to
the decrease of the reaction yield (Table 1, entries 20–22).
shown in Table 2, most of the substrates tested could afford the
expected products in moderate to good yields. From the results,
2
it is clear that the position of substituent of R affected the yield
previous work
of corresponding products. Taking methyl as an example, when it
was at para-position, the expected product 3b could be produced
in 74% yield. And a lower yield of 54% was obtained when the same
group was at meta-position. In contrast, no desired product could
be produced with a change of the methyl group to the ortho-posi-
tion. Furthermore, there is no clear electron effect of the sub-
R1
f unctionalization/ cyclization
R3
O
(eq 1)
R2
R1
O
R3 = CF
3
2 2
, CF CO Et, RCO,
, PO(OR)
RSO
2
2
, ArSe
2
2
R2
stituent R . Besides the methyl group, when the R group was
t
para- Bu, para-chloro, para-iodo, para-trifluoromethyl, or para-
O
O
functionalization/
R1
dearomatization-cyclization
R4
O
methoxyl group, the substrates all gave the expected products in
good yield (Table 2, products 3d, 3e, 3g, 3l, and 3m). And the pres-
ence of the halogen atom in the products would provide an addi-
tional position for further derivatization. The substrates with
(eq 2)
O
O
R4 = I, Br, F, CF
, tetrahydrofuran-2-yl
3
1
current work
different R groups were also tested with 1,4-dioxane under the
O
O
optimal reaction conditions, and the corresponding products were
formed in moderate yields (Table 2, products 3h–3m). Next, we
attempted some other reagents that have been used in radical-
involved reactions. Among them, the use of 1-butoxybutane,
tetrahydropyran (THP), and cyclohexane all led to the desired
products in moderate to good yields (Table 2, products 3n–3p),
and the use of tetrahydrofuran only afforded the expected product
O
O
2a
O
(
eq 3)
PhI(OAc)
0 °C
2
O
O
8
O
O
O
O
1a
not observed
observed
3
q in a lower yield of 20%. While no desired products were
Scheme 1. Addition/cyclization of aryl 3-arylpropiolate.

J. Wang et al. / Tetrahedron Letters 57 (2016) 1239–1242
1241
Table 2
a
BPO-promoted addition/ipso-cyclization/decarboxylation of aryl 3-arylpropiolate
O
O
BPO (1 equiv), TEMPO (1 equiv)
100
+
+
R1
o
C
O
O
R1
BPO (1 equiv)
O
+
O
O
R3
1
00 o
C
R2
R3
1b (0.24 mmol)
2a (1 mL)
3b (0%)
R2
R3 = O, C
O
1
O
2
3
O
O
BPO (1 equiv), BHT (1 equiv)
00 o
1
C
O
O
O
1
b (0.24 mmol)
2a (1 mL)
3b (0%)
O
O
O
O
Scheme 2. Preliminary mechanism studies.
O
O
O
O
tBu
Cl
3
b
3c
(54%)
3d
3e
(64%)
(
74%)
b
O
(
70%, 52% )
O
Ph
Cl
Ph
O
O
O
O
O
O
O
O
Ph
Cl
Cl
O
I
O
O
O
O
I
O
O
3
f
3g
2
a
(
68%)
(58%)
3i
53%)
O
O
O
O
3
h
(
1a
3a
(
44%)
O
Cl
3
F C
MeO
O
II
O
2
a
O
O
O
O
O
O
O
O
O
O
O
O
O
O
III
VI
CO
2
Cl
3k
3
F C
MeO 3m
ipso-cyclization
3
j
3l
-
(
59%)
(64%)
(51%)
(73%)
O
O
O
O
O
O
O
O
O
nBu
O
IV
O
aromatization/
C-O bond cleavage
V
3
o
3p
3q
3
n
(
41%)
(68%)
(20%)
(
56%)
Scheme 3. Plausible mechanism of the reaction.
a
Reaction conditions: without other notifications, all of the reactions were per-
formed with 1 (0.23 mmol) in 2 (1 mL) in the presence of BPO (1 equiv) under Ar.
The yields are isolated yield.
The reaction was carried out with 1d (1 g, 3.6 mmol) in 1,4-dioxane (15 mL) with
BPO (1 equiv) under Ar. The yield is isolated yield.
gen abstraction process. The addition of II to the carbon–carbon
triple bond led to the vinyl radical intermediate III, which would
produce intermediate IV through an intramolecular dearomatiza-
tion–cyclization. Next, the aromatization/C–O bond cleavage
would afford the carboxyl radical intermediate V, which under-
went a decarboxylation to form vinyl radical VI. Finally, another
hydrogen abstraction of 2a by intermediate VI would give the
product 3a.
b
observed by using other nitrogen-containing reagents, that is, mor-
pholine, 4-methylmorpholine, and N-methylpiperidine. Addition-
ally, in order to support the practical utility of this
transformation, we have carried out it in gram scale with substrate
1
d as an example, and obtained the product 3d in a yield of 52%. It
should be admitted that the stereoselectivity for the formation of
carbon–carbon double bond of the desired products is not satisfac-
tory, and the product with two different aromatic groups were all
confirmed as a mixture of two E/Z isomers in about 1:1 ratio.
In order to better understand the reaction mechanism, some
control experiments were carried out (Scheme 2). When the reac-
tion between substrates 1b and 2a was performed in the presence
of 1 equiv of TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy) or BHT
Conclusions
In conclusion, a BPO-promoted tandem reaction between aryl
3-arylpropiolate and ether (cycloalkane) has been developed, in
which
a radical-participated addition/dearomatization–cycliza-
tion/decarboxylation cascade was involved. This procedure might
provide an alternative strategy for the synthesis 1,1,2-trisubsti-
tuted ethylenes. Currently, further studies related to this type of
transformation are on-going in the same group.
(
dibutylhydroxytoluene), this tandem reaction was totally inhib-
ited. No product 3b could be detected, and most of the 1b was left
unreacted. These experiments indicated that such a transformation
might be a radical-involved process.
Acknowledgements
Based on the above experimental results, the mechanism for
this reaction is proposed (Scheme 3). Using the reaction of 1a
and 2a as an example, the reaction should be initiated by the ther-
This work was supported by the NSFC (Nos. 21202073 and
21472077), the Fundamental Research Funds for the Central
Universities (lzujbky-2015-k12), and the Opening Project of Key
Laboratory of Drug Targeting and Drug Delivery System, Ministry
of Education (Sichuan University).
1
0
mal homolysis of BPO to give an oxygen-centered radical I, which
reacted with 2a to afford radical intermediate II through a hydro-

1
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747.
9
During our manuscript preparation, Han and co-workers reported a similar
type of transformation using cycloalkane as coupling reagent, Ni, S.; Zhang, Y.;
Xie, C.; Mei, H.; Han, J.; Pan, Y. Org. Lett. 2015, 17, 5524.
4
4
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For selected examples with carbon–carbon double bond: (a) Wu, T.; Mu, X.; Liu,
G. Angew. Chem., Int. Ed. 2011, 50, 12578; (b) Zhang, H.; Chen, P.; Liu, G. Synlett
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0. (a) Cass, W. E. J. Am. Chem. Soc. 1947, 69, 500; (b) Fang, L.; Chen, L.; Yu, J.; Wang,
2
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