[3,3]-Sigmatropic Rearrangement of Aryl Fluoroalkyl Sulfoxides with Alkyl Nitriles

Article abstract of DOI:10.1002/ejoc.201901577

Herein we report the ortho-cyanoalkylation of aryl fluoroalkyl sulfoxides with alkyl nitriles. The reaction proceeds through an “assembly/deprotonation” triggered [3,3]-rearrangement and allows the incorporation of two valuable functional groups including the cyano group and difluoromethylthio group into arenes. As a consequence, a wide range of ortho-cyanoalkylated difluoromethylthio arenes were produced with high efficiency under mild and environmentally friendly conditions. Remarkably, the reaction proceeds smoothly with the electron-donating group substituted arenes which can be challenging to the reaction of non-fluoroalkyl sulfoxides. This beneficial effect can be attributed to the unique electronegativity of fluoroalkyl substituents.

Full text of DOI:10.1002/ejoc.201901577

A Journal of
Accepted Article
Title: [3,3]-Sigmatropic Rearrangement of Aryl Fluoroalkyl Sulfoxides
with Alkyl Nitriles
Authors: Mengjie Hu, Jia-Ni He, Yanping Liu, Taotao Dong, Mengyuan
Chen, Chao Yan, Yulu Ye, and Bo Peng
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To be cited as: Eur. J. Org. Chem. 10.1002/ejoc.201901577
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10.1002/ejoc.201901577
European Journal of Organic Chemistry
COMMUNICATION
[3,3]-Sigmatropic Rearrangement of Aryl Fluoroalkyl Sulfoxides
with Alkyl Nitriles
Mengjie Hu,[a,b] Jia-Ni He,[a,b] Yanping Liu,[a] Taotao Dong,[a] Mengyuan Chen,[a] Chao Yan,[a] Yulu Ye,[a]
and Bo Peng*[a]
Dedication ((optional))
Abstract: Herein we report the ortho-cyanoalkylation of aryl
fluoroalkyl sulfoxides with alkyl nitriles. The reaction proceeds
through an “assembly/deprotonation” triggered [3,3]-rearrangement
and allows the incorporation of two valuable functional groups
including the cyano group and difluoromethylthio group into arenes.
As
a
consequence,
a
wide range of ortho-cyanoalkylated
difluoromethylthio arenes were produced with high efficiency under
mild and environmentally friendly conditions. Remarkably, the
reaction proceeds smoothly with the electron-donating group
substituted arenes which can be challenging to the reaction of non-
fluoroalkyl sufloxides. This beneficial effect can be attributed to the
unique electronegativity of fluoroalkyl substituents.
Introduction
Cyanoalkylated arenes and their derivatives are often found as
structural motifs in drugs1 and bioactive compounds2. The cyano
group can also be readily converted into other functional groups
(FGs) such as carboxylic acids, amides, aldehydes, amines, and
ketones.3 Furthermore, cyanoalkylated arenes are useful
precursors to an array of N-heterocycles including thiozoles,
oxazolines, tetrazoles, imidazoles, and triazoles.4 On the other
hand, the difluoromethylthio group is generally considered as a
highly lipophilic weak hydrogen bonding donor and thus plays
critical roles in many pharmaceuticals5, agrochemicals6 and
bioactive compounds7. Therefore, the cyanoalkylated arene and
the difluoromethylthio group are highly desirable in both the
synthetic chemistry and drug discovery process.8,9
Scheme 1. Our previous work and hypothesis here.
According to our previous studies, the hypothesized reaction
would consist of three major stages: (1) Tf2O initiated
electrophilic assembly of aryl fluoroalkyl sulfoxide with alkyl
nitrile forms an imine-sulfonium intermediate I; (2) Base
promoted deprotonation of I generates a ketenimine-sulfonium
species II; (3) Intermedaite II undergoes [3,3]-rearrangement
and rearomatization to afford the final product. Since the [3,3]-
rearrangement would proceed rapidly with the congestion
release of ketenimine moiety of II,10a the success of the reaction
would rely on the other two critical steps including the “assembly”
and “deprotonation” steps. It should be noted that the ortho-
cyanoalkylation of aryl perfluoroalkyl sulfoxides with alkyl nitriles
has also been reported by Magnier and coworkers.12 In that
case, only anhydride (Tf2O) was used for the coupling process.
However, the reported base-free protocol merely resulted in the
deterioration of aryl sulfoxide (Table 1, entry 4).
In recent years, we have been interested in exploring the use
of “assembly” protocol for the development of aromatic [3,3]-
rearrangements.10,11 For example, we have recently
demonstrated
a
metal-free ortho-cyanoalkylation of aryl
sulfoxides through an “assembly/deprotonation” triggered [3,3]-
rearrangement, which allows the synthesis of α-aryl nitriles in a
redox-neutral manner (Scheme 1, eq 1).10a Inspired by that work,
we wondered whether the reaction pattern can be applicable to
aryl fluoroalkyl sulfoxides that would produce ortho-
cyanoalkylated difluoromethylthio arenes by incorporating two
valuable functional groups into arenes simultaneously (eq 2).
Results and Discussion
[a]
M. Hu, J. N. He, Y. Liu, T. Dong, M. Chen, C. Yan, Y. Ye, Prof. B.
Peng
Key Laboratory of the Ministry of Education for Advanced Catalysis
Materials, Zhejiang Normal University
Jinhua 321004, China
E-mail: pengbo@zjnu.cn
Homepage:
http://sky.zjnu.edu.cn/2014/0127/c4853a85463/page.htm
These authors contributed equally.
To test our hypothesis, we examined the reaction of aryl
fluoroalkyl sulfoxide 1a with alkyl nitrile 2a (Table 1). To our
delight, the reaction afforded the desired ortho-cyanoalkylated
product 3aa with modest yield (48%) under the reported
conditions previously used for ortho-cyanoalkylation of non-
fluoroalkyl sulfoxides (Tf2O, -30 °C, 10 min; DABCO, -30 °C, 10
min)10a (Table 1, entry 1). Simply prolonging the reaction time (t1)
[b]
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10.1002/ejoc.201901577
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COMMUNICATION
Table 1. Optimization of reaction conditionsa
challenging for conventional aromatic cyanoalkylation reactions.8
Accordingly, the excellent functional group compatibility makes
entry
1
base
T (°C )
-30
-30
-30
-30
-30
-30
-30
-20
-40
-30
-30
t 1
10 min
1 h
t 2
yield (%)b
DABCO
DABCO
DABCO
none
10 min
10 min
10 min
10 min
10 min
10 min
10 min
10 min
10 min
1 h
48
85
62
0
2
3
6 h
4
1 h
5
pyridine
DIPEA
DBU
1 h
trace
68
16
80
75
78
77
6
1 h
7
1 h
8
DABCO
DABCO
DABCO
DABCO
1 h
9
1 h
10
11
1 h
1 h
6 h
[a] Reaction conditions: 1a (0.5 mmol), 2b (1.5 equiv) and Tf2O (1.5 equiv),
DCM (0.17 M), T(°C), t1 (min or h); then base (2.0 equiv), T(°C), t2 (min or h).
[b] Isolated yield.
for the electrophilic assembly of 1a with 2a could significantly
improve the yield of 3aa (entry 2). The best yield (85%) was
obtained when 1 h (t1) was applied. However, further prolonging
t1 to 6 h resulted in a lower yield (62%). This was probably due
to the deterioration of in situ-assembled imine-sulfonium
intermediate I when longer “assembly” time (t1) was used
(Scheme 1, eq 2). Further screen of bases demonstrated that
DABCO was more suitable than other organic bases such as
pyridine, Hünig's base, and DBU. A slightly increase or drop in
reaction temperature could not further improve the yield of 3aa
(entries 7 and 8). Moreover, 10 minutes (t2) was found to be
adequate for the “deprotonation” step by comparing the results
of the use of 1 h and 6 h (entries 9 and 10). Therefore, the
“deprotonation” process is similar to that of non-fluoroalkyl
sulfoxides that we have previously studied.10a Eventually, the
optimum conditions (Tf2O, -30 °C, 1 h; DABCO, -30 °C, 10 min)
was identified for the reaction (entry 2).
With the best conditions in hand, we examined the generality
of the reaction with an array of alkyl nitriles 2 (Scheme 2). To our
delight, a wide range of alkyl nitriles 2a-2s were found to be
suitable for the reaction. Regardless of the length of alkyl chains
at α-position of alkyl nitriles (2a and 2b), the reactions afforded
cyanoalkylated products 3aa and 3ab in good yields (85% and
78%, respectively). However, acetonitrile 2c as the simplest
alkyl nitrile furnished 3ac in a relatively low yield (49%).
Remarkably, the reaction exhibited excellent functional group
compatibility. Functional groups including alkyl halides/
pseudohalides (3ad, 3ae, 3am, 3an, 3ap, and 3ag), ethers (3af),
esters (3ah, 3aj-3ao) and internal alkynes (3ap) were all well
tolerated in the reaction. It is worthy to note that highly
electrophilic functional groups such as benzylic chloride (3an), α,
β-unsaturated ester (3ao) and alkynyl bromide (3ap) were also
compatible with the reaction conditions. This result was
impressive since these tolerated functionalities can be
Scheme 2. Scope of alkyl nitriles. [a] Unless otherwise noted, the reaction was
performed under optimized conditions. [b] 3.0 equiv of nitrile 2i was used. [c]
The mixture of 1a and 2 (2j-l and 2n) was stirred under -50 °C for 12 h before
the addition of DABCO.
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10.1002/ejoc.201901577
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Scheme 3. Reactions of aryl fluoroalkyl sulfoxide1a with activated alkyl nitriles.
the reaction complementary to other known methods. In addition,
stereo-hindered substrates such as β-methyl substituted alkyl
nitrile (2r), and cyclopropane nitrile (2s) also proved suitable for
the reaction although 3as bearing a new quaternary carbon
center was obtained in a relatively low yield (50%). Encouraged
by the obtained results, we further studied the scope of aryl
sulfoxides 1 (Scheme 2, bellow the dashed line). Gratifyingly,
different from non-fluoroalkyl sulfoxides that have been studied
previously,10a aryl fluoroalkyl sulfoxides bearing electron
donating groups on phenyl rings (1b, 1e, 1f, and 1g) could also
produce the desired cyanoalkylated products (3ba, 3ea, 3fa,
3ga) in good yields. In addition, stereo-hindered ortho-
substituted aryl sulfoxides 1e was also suitable for the reaction.
This is remarkable since the corresponding ortho-methyl aryl
non-fluoroalkyl sulfoxides have proved unfeasible for this type of
rearrangement. We suspected that the enlarged scope of aryl
substituents could benefit from the increased electronegative
effect of fluoroalkyl groups which would facilitate the electrophilic
assembly of aryl fluoroalkyl sulfoxides with alkyl nitriles to form
imine-sulfonium intermediate I (Scheme 1, eq 2). Remarkably, in
addition to the benzoyl group (1a-1g,), ester or amide groups
(1h and 1i) substituted fluoroalkyl sulfoxides also produced the
desired products 3ha and 3ia with high efficiency. These two
functional groups provided a versatile platform for further
elaboration of the products.
Scheme 4. Gram-scale reaction and further elaboration of products.
Conclusions
In summary, we have developed an efficient [3,3]-rearrangement
of aryl fluoroalkyl sulfoxides with alkyl nitriles that allows the
synthesis of valuable ortho-cyanoalkylated difluoromethylthio
arenes. In contrast with non-fluoroalkyl sulfoxides that we
studied previously, the aryl fluoroalkyl sulfoxides owns a broader
scope of aryl sulfoxides. This can be attributed to the
electronegative effect of fluoroalkyl group. The notable features
of the reaction include mild conditions, exclusive selectivity, the
use of readily available and environmental friendly reagents, and
the broad substrate scope for both coupling partners.
Applications of the method and further exploiting the
rearrangement triggered by the “assembly/deprotonation”
sequence are underway in our laboratory.
Experimental Section
General procedure for the synthesis of ortho-cyanoalkylated
difluoromethylthio arenes 3. To a mixture of aryl sulfoxide (1, 0.5 mmol)
and alkyl nitrile (2, 0.75 mmol) in DCM (3 mL) was added Tf2O (126 μL,
0.75 mmol) under -30 °C. After stirring for 1 h, DABCO (112 mg, 1.0
mmol) was added to the mixture under the same temperature. The
mixture was then stirred for another 10 min. After that, the mixture was
passed through a short silica gel column and concentrated under vacuum.
The resulting residue was further purified by column chromatography
over silica gel eluting with a gradient of EtOAc/Petroleum ether (0−50%)
to afford 3.
Interestingly, alkyl nitriles 2t and 2u bearing an electron-
withdrawing group at α-position displayed a different reactivity
(Scheme 3). Even in absence of bases, these active alkyl nitriles
could be coupled with aryl fluoroalkyl sulfoxide 1a leading to
cyanoalkylated products 3at and 3au in modest to good yields.
This result was probably due to the enhanced acidity of α-proton
of in situ-generated imine-sulfonium intermediate III, which could
readily be deprotonated by counter anion to give the
rearrangement
precursor,
namely
ketenimine-sulfonium
Preparation of 2-(2-((difluoromethyl)thio)phenyl)pentanenitrile (4aa).
To a solution of 3aa (2.1 g, 8.7 mmol) in PhMe (45 mL) was added H2O
(2.2 g, 121.8 mmol) at room temperature. The reaction mixture was
gradually warmed to 100 °C and stirred for 2 h. After cooling to room
temperature, the mixture was dissolved in EtOAc and washed with H2O.
The organic layer was separated, dried over Na2SO4, and concentrated.
The resulting residue was further purified by column chromatography
over silica gel eluting with a gradient of EtOAc/Petroleum ether (10−25%)
to afford 4aa in 90% (1.9 g).
intermediate IV. This result also reflects the importance of base
in the reaction of simple alkyl nitriles (Table 1, entry 4).
To demonstrate the practicability of the reaction, a gram-scale
reaction of 1a and 2a was performed under the optimum
conditions (Scheme 4). The reaction at gram-scale still afforded
3aa in good yield (87%). The benzoyl group of 3aa could be
readily removed under
a
reported basic conditions.13 As
mentioned in the introduction, the cyano group was indeed
readily converted to other functionalities such as amide (5aa),
carboxylic acid (6aa), ketone (7aa) and amine (8aa) through
simple hydrolysis, nucleophilic addition, and reduction,
respectively. The diverse elaboration of cyano group
demonstrated the utility of the reaction.
Preparation of 2-(2-((difluoromethyl)thio)phenyl)pentanamide (5aa).
To a solution of 4aa (121 mg, 0.5 mmol) in DMSO (1 mL) were
sequentially added H2O2 (30% aq., 140 μL) and K2CO3 (14 mg, 0.1 mmol)
at 25 °C. After stirring for 12 hours, the mixture was diluted with H2O,
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10.1002/ejoc.201901577
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COMMUNICATION
extracted with DCM and dried over Na2SO4. Then the mixture was
filtrated and concentrated under vacuum. The resulting residue was
further purified by column chromatography over silica gel eluting with a
gradient of EtOAc/Petroleum ether (10−33%) to afford 5aa in 98% (127
mg).
[6]
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Preparation of 2-(2-((difluoromethyl)thio)phenyl)pentanoic acid (6aa).
To a solution of KOH (278 mg, 5 mmol) in EtOH (2 mL) and H2O (0.5 mL)
was added 4aa (121 mg, 0.5 mmol). The mixture was stirred under reflux
for 20 hours. After cooling to room temperature, the mixture was diluted
with H2O, acidified to pH = 1~2 (con. HCl), extracted with CHCl3 and
dried over Na2SO4. Then the mixture was filtrated and concentrated
under vacuum. The resulting residue was further purified by column
chromatography over silica gel eluting with a gradient of MeOH/DCM
(0−6%) to afford 6aa in 86% (112 mg).
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C.-J. Li, Chem. Sci. 2018, 9, 5781–5786.
Preparation of 5-(2-((difluoromethyl)thio)phenyl)oct-1-en-4-one (7aa).
To a mixture of 4aa (121 mg, 0.5 mmol), allyl bromide (91 mg, 0.75 mmol)
and Zn (powder, 131 mg, 2.0 mmol) in THF (2.0 mL) was added
anhydrous AlCl3 (27 mg, 0.2 mmol) at -15 °C under N2 atmosphere. The
mixture was stirred for 3 h at the same temperature. Then to the mixture
was added HCl (1.0 M, 5 mL) dropwise. After stirring for another 30 min,
the mixture was neutralized with NaHCO3 (sat.), extracted with DCM. The
organic layer was separated, dried over Na2SO4, and concentrated. The
resulting residue was further purified by column chromatography over
silica gel eluting with a gradient of EtOAc/Petroleum ether (5−10%) to
afford 7aa in 78% (110.3 mg).
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Preparation of 2-(2-((difluoromethyl)thio)phenyl)pentan-1-amine
(8aa). To a solution of LiAlH4 (1 M in THF, 1 mL) in diethyl ether (1 mL)
was added a solution of 4aa (121 mg, 0.5 mmol) in diethyl ether (0.5 mL)
dropwise for 1 hour at 0 °C under N2 atmosphere. Then the mixture was
gradually warmed to room temperature. After stirring for 24 hours, to the
mixture was added NaOH (10% aq., 2 mL). The mixture was stirred for
12 hours, then extracted with EtOAc, filtrated through Kieselguhr and
dried over Na2SO4. After that the mixture was filtrated and concentrated
under vacuum. The resulting residue was further purified by column
chromatography over silica gel eluting with a gradient of MeOH/DCM
(0−6%) to afford 8aa in 40% (49 mg).
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Acknowledgments ((optional))
This work is supported by Zhejiang Normal University and the
National Natural Science Foundation of China -21502171.
Keywords: rearrangement • cyanoalkylation • difluoromethylthio
group • sulfoxide • C-H functionalization
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Mengjie Hu, Jia-Ni He, Yanping Liu,
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This work describes the ortho-cyanoalkylation of aryl fluoroalkyl sulfoxides with alkyl
nitriles through an “assembly/deprotonation” triggered [3,3]-rearrangement, which
enables the installation of two valuable functional groups including the cyano group
and difluoromethylthio group into arenes.
[3,3]-Sigmatropic Rearrangement of
Aryl Fluoroalkyl Sulfoxides with Alkyl
Nitriles
*one or two words that highlight the emphasis of the paper or the field of the study
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