A domino reaction of 2-isocyanophenyloxyacrylate and aryne to synthesize arenes with vicinal olefin and benzoxazole

Article abstract of DOI:10.1039/c8cc05735d

An unusual domino reaction of 2-isocyanophenyloxyacrylate and aryne has been disclosed. The present strategy experiences nucleophilic addition, Michael addition, carbon-oxygen cleavage, and cyclization, thus enabling the quick aryne vicinal difunctionalization by the installation of a benzoxazole and an olefin.

Full text of DOI:10.1039/c8cc05735d

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Domino reaction of 2-isocyanophenyloxyacrylate and aryne to
synthesize arenes with vicinal olefin and benzoxazole
Shikuan Su,a Jianxiong Li,b Mingming Sun,b Hongbin Zhao,b Yali Chen, *a,b and Jian Li*a,b
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
www.rsc.org/
An unusual domino reaction of 2-isocyanophenyloxyacrylate and synthesis of many carbocycles and heterocycles.13 Remarkably,
aryne has been disclosed. The present strategy experiences many achievements have been made on the multicomponent
nucleophilic addition, Michael addition, carbon-oxygen cleavage, reactions involving isocyanide and aryne.14 The initial
and cyclization, thus enables the quick aryne vicinal successful example on three component reaction containing
difunctionalization by the installation of a benzoxazole and an both isocyanide and aryne was reported by Yoshida et. al.
olefin.
(Scheme 1a).14a Following these works, Huang and co-workers
described another interesting multicomponent reaction of
Arynes represent one of the most reactive intermediates,
which have been broadly used in various carbon-carbon and
carbon-heteroatom bond-forming reactions.1,2 As such,
reactions involving the insertion of aryne into C-C,3 C-N,4 C-O,5
and other bonds have been well documented.6 Furthermore,
the aryne-based Diels-Alder reaction, [2+5], [2+8] and many
other pericyclic reactions have been intensively investigated
for the construction of various benzo-fused frameworks.7
Usually, aryne can serve as efficient building block for the
synthesis of diverse difunctionalized arenes. Of late, Li and co-
workers discovered a new aryne precursor,8 thus providing a
quick access to assemble three consecutive functional groups
on a benzene ring in an efficient manner. In particular, the
generation of aryne from ortho-(trimethylsilyl)aryl triflate
developed by Kobayashi under mild conditions appears to be
the key to the success of these reactions.9 Regardless of the
transition-metal-catalyzed reactions, many efforts have also
been devoted to the exploration of new transition-metal-free
reactions.10
a) Multicomponent reaction of aryne, isocyanide, and aldehyde
NR2
TMS
OTf
O
KF, 18-crown-6
THF
R1
+
R2
+
(1)
R1
NC
O
R3
H
R3
b) Multicomponent reaction of aryne, isocyanide, and alkyne
R2
TMS
N
CsF
toluene/MeCN
R1
+
+
NC
R3
(2)
R1
R2
R1
OTf
R3
c) This work
R2O2C
O
CO2R1
CsF
OTf
TMS
R1
O
N
R3
(3)
CH3CN
R1
NC
R3
Scheme 1. Representative examples involving isocyanide and
aryne
aryne, isocyanide, and terminal alkyne, thus providing a
straightforward route to polysubstituted pyridines and
isoquinolines (Scheme 1b).14b In addition, Stoltz and co-
workers discovered the aryne-intercepted version of the
Passerini reaction to furnish phenoxyiminoisobenzofuran
motifs.14c In contrast to multicomponent reactions, there are
few study on the direct two-component reaction of
functionalized isocyanides and arynes.15 In view of the diverse
reactivity of isocyanide, more concise methods combining
functionalized isocyanide and aryne remain highly in demand
to expand the realm of aryne chemistry. Recently, the
exploration of new reactivity of isocyanides has been a new
research focus and much important progress has been made
with the outstanding contributions of Zhu and Xu.16 As a
Owing to their versatile reactivity, isocyanides have
received considerable attention from organic community.11
For instance, the classical carbine-like reactivity made them
particularly reaction partners in various multicomponent
reactions (IMCRs) ever since Passerini and Ugi reaction.12
Additionally, these reactive species were also widely used in
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continuation of our previous works on isocyandie chemistry entry 7). Encouraged by these results, we then turned our
and heterocycle synthesis,17 herein we wish to report the attention to the other influence factors. The experimental
newly designed functionalized isocyanide containing outcome demonstrated that higher temperature favored the
phenyloxyacrylate and its first transition-metal-free reaction formation of 3a, whereas lower yields were observed when
with aryne.
reactions were performed at 40 oC (Table 1, entries 10-11).
Finally, the yield of 3a was improved to 71% when the ratio of
Table 1. Reaction optimizationa
substrate 2a:1a was adjusted to 1.5:1.
MeO2C
O
OTf
O
conditions
CO2Me
NC
TMS
N
3a
1a
2a
Entry
F source (equiv)
Temp (oC)
Solvent
Yield (%)b
1
2
CsF (2.0)
KF/18ꢀCꢀ6 (2.0)
TBAF (2.0)
CsF (3.0)
CsF (4.0)
CsF (4.0)
CsF (4.0)
60
60
60
60
60
60
60
60
60
40
80
THF
THF
18
<5
0
THF
3
THF
4
26
31
NR
46
18
<5
25
53
61
68
71
THF
5
Toluene
CH3CN
DME
6
7
8
CsF (4.0)
CsF (4.0)
CsF (4.0)
CsF (4.0)
CsF (4.0)
CsF (4.0)
CsF (4.0)
1,4ꢀdioxane
CH3CN
CH3CN
CH3CN
CH3CN
9
10
11
12c
13c,d
14c,e
80
80
80
CH3CN
a
Unless otherwise noted, all reactions were carried out with 0.5
Scheme 2 Scope of the reaction with respect to the functionalized
a
mmol 2ꢀisocyanophenyloxyacrylate 1a, 0.5 mmol benzyne precursor
2a, fluorine source, in 5 mL solvent, 24 hours. Yields of product
isocyanide 1. Reaction condition A: 0.5 mmol isocyanide 1, 0.75
b
mmol benzyne precursor 2a, CsF (4.0 equiv), CH3CN (5 mL), 80 oC,
c
d
36 hours. b Yields of product after silica gel chromatography.
after silica gel chromatography. Reaction time is 36 h. The ratio
of 2a:1a was 1.2:1. e The ratio of 2a:1a was 1.5:1.
To establish the scope and limitation of present approach,
We initially examined the model reaction of ethyl 3-(2-
isocyanophenoxy)acrylate (1a) and benzyne precursor (2a) to
exploit the possible domino conversion. As shown in Table 1,
upon treatment with the mixture in THF essentially afforded a
new product 3a in 18% yield (Table 1, entry 1). Next,
investigation on the effect of parameters including fluorine
source, catalyst loading, temperature, and solvent was
conducted to enhance the yield of 3a. Of the fluorine sources
tested, KF/18-C-6 led to very poor performance while TBAF
showed no reactivity (Table 1, entries 2-3). The experimental
results also revealed that the fluorine source loading had a
significant impact on present transformation. The yield of 3a
was elevated to 31% when 4.0 equivalents CsF was added
(Table 1, entry 5). Reactions with other solvents including
Toluene, CH3CN, DME, and 1,4-dioxane were also screened to
make some improvement. Gratifyingly, the employment of
CH3CN as solvent increased the yield of 3a significantly (Table 1,
the compatibility of substrates
1 with substituents at the
aromatic ring bearing the isocyano group was firstly evaluated.
As shown in Scheme 2, a series of substituents including
methyl, acetyl, halide, ester groups at position 6, 5, 4 of the
aromatic ring in substrate
1
were found to be compatible to
3j. Furthermore, the
produce the desired compounds 3a
-
structures of compounds 3a and 3g were unambiguously
confirmed by single crystal X-ray analysis.18 Unfortunately, no
reaction occurred when substituent was present at position 3
of the aromatic ring in
1. Next, the experimental results
showed that an array of substituted olefins with electron-
withdrawing groups including ethyl acetate, acetyl, benzoyl,
and sulphonyl groups were well tolerated to furnish the
desired products 3k
After showing a broad scope of different ethyl 3-(2-
isocyanophenoxy)acrylate , we then focused our attention to
-3n.
1
the feasibility of substituted aryne precursors. First, symmetric
2 | J. Name., 2012, 00, 1-3
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Based on the aforementioned results and previous reports,
a plausible reaction mechanism is described in Scheme 4 to
explain the formation of product. The beginning of present
reaction involves the generation of a reactive zwitterionic
intermediate
A from 1a and 2a. After that, two following
reaction pathways seem to be possible. In path a,
intramolecular Michael addition on the carbon-carbon double
bond takes place to generate the enolate
oxygen rupture occurs to yield intermediate
B
. Next, carbon-
C
. On the other
hand, direct benzoxazole formation on intermediate
generates an oxonium intermediate , which then undergo
olefin migration via a five-membered ring transition state to
give product 3a
A
D
.
Scheme 5. Synthetic application of the product
Scheme 3 Scope of the reaction with respect to the aryne presursor 2.
a
b
Reaction condition A.
chromatography.
Yields of product after silica gel
To further illustrate the utility of present protocol, more
detailed investigation regarding the application of the
products was carried out (Scheme 5). From the standpoint of
structural characters, substrate 3a contains a benzoxazole
which might function as a directing group.19 In this light, the
aryne precursors were used to react with several substituted
substrate containing the acrylate and alkenone unit to form
the desired products 4a 4f Then, the reactions with
1
reactions of 3a and acrylates 5a, 5b were performed in the
-
.
presence of catalytic amount of rhodium catalyst, respectively.
Then, the ortho-olfination reaction with styrene 6c also
proceeded well to furnish 6c albeit somewhat lower yield
(Scheme 5, eq 1). Finally, the amidation reaction with aromatic
unsymmetrical aryne precursors were conducted under
standard conditons. To our delight, reaction with aryne
precursor 2d containing ortho-methoxy substitution afforded
the corresponding products 4g and 4g’ in good regioselectivity.
Moreover, aryne precursor 2e having meta-substituent was
amine
7 worked well to yield the corresponding products 8
(Scheme 5, eq 2).
found to be compatible substrate to yield 4h and 4h’
.
In conclusion, we have described an unusual reaction with
a newly designed 2-isocyanophenyloxyacrylate and aryne. This
domino reaction introduces a benzoxazole ring and an olefin
into the aromatic ring of aryne spontaneously, thus providing a
new reactivity mode for both isocyanide and aryne chemistry.
Furthermore, the unique structure of the products also
enables further olefination via the Rhodium-catalyzed C-H
activation. Other distinguished features include the absence of
any catalyst and a wide substrate scope. Further study of
present reaction is still underway in our laboratory.
The authors gratefully acknowledge financial support from
National Key Research and Development Program of China
(2017YFB0102900) and National Natural Science Foundation of
China (21272146). This work is also sponsored by Natural
Science Foundation of Shanghai (18ZR1413900) and Shanghai
Pujiang Program (17PJD016).
Scheme 4. Proposed mechanism
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