Iron-Catalyzed Azidoalkylthiation of Alkenes with Trimethylsilyl Azide and 1-(Alkylthio)pyrrolidine-2,5-diones

Article abstract of DOI:10.1002/adsc.201600133

A simple, efficient and practical iron-catalyzed azidoarylthiation of alkenes has been developed at room temperature, and the corresponding products containing ortho-sited sulfide and azide units were obtained in moderate to good yields with good tolerance of functional groups. The protocol uses readily available 1-(alkylthio)pyrrolidine-2,5-diones and trimethylsilyl azide as the alkylthiation and azidation reagents, respectively, inexpensive and environmentally friendly iron chloride as the catalyst without addition of any ligand and additive. (Figure presented.).

Full text of DOI:10.1002/adsc.201600133

UPDATES
DOI: 10.1002/adsc.201600133
Iron-Catalyzed Azidoalkylthiation of Alkenes with Trimethylsilyl
Azide and 1-(Alkylthio)pyrrolidine-2,5-diones
Jipan Yu,a Min Jiang,a Zhixuan Song,a Tiancheng He,a Haijun Yang,a and Hua Fua,*
a
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of
Chemistry, Tsinghua University, Beijing 100084, Peopleꢀs Republic of China
Fax : (+ 86)-10-6278-1695; e-mail: fuhua@mail.tsinghua.edu.cn
Received: February 10, 2016; Revised: June 12, 2016; Published online: && &&, 0000
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/adsc.201600133.
Abstract: A simple, efficient and practical iron-cat-
alyzed azidoarylthiation of alkenes has been devel-
oped at room temperature, and the corresponding
products containing ortho-sited sulfide and azide
units were obtained in moderate to good yields
with good tolerance of functional groups. The pro-
tocol uses readily available 1-(alkylthio)pyrrolidine-
2,5-diones and trimethylsilyl azide as the alkylthia-
tion and azidation reagents, respectively, inexpen-
sive and environmentally friendly iron chloride as
the catalyst without addition of any ligand and ad-
ditive.
diones are interesting alkylthiation reagents, and they
were used in various organic reactions by us and
other groups.[14] Very recently, we have developed
a catalyst-free isothiocyanatoalkylthiation of styrenes
with (alkylthio)pyrrolidine-2,5-diones and trimethyl-
silyl isothiocyanate.[15] Inspired by the excellent re-
sults, we here report an azidoalkylthiation of alkenes.
As shown in Table 1, the three-component coupling
of styrene (1a), 1-(phenylthio)pyrrolidine-2,5-dione
(2a) and trimethylsilyl azide was selected as the
model to optimize the conditions. At first, the reac-
tion was performed under the same conditions (DMF
as the solvent at 908C under argon) as for the isothio-
cyanatoalkylthiation of styrenes.[15] Unfortunately,
only a trace amount of the target product (3a) was
observed. One possible reason is that the azido group
has weaker nucleophilicity than the isothiocyano.
Next, various catalysts were screened in 1,2-dichloro-
ethane (DCE) at room temperature under argon (en-
Keywords: alkylthiation; azidation; difunctionaliza-
tion; iron-catalyzed reaction; synthetic methods
Transition metal-catalyzed difunctionalizations of al- tries 2–13), and FeCl3 provided the highest yield
kenes have attracted much attention,[1] and some in- (entry 2). Other azido sources were tested, and they
teresting reactions such as dioxygenation,[2] aminooxy- gave poor results (entries 14 and 15). The effect of
genation,[3] diamination,[4] aminohalogenation,[5] and solvents was investigated (compare entries 2, 16–20),
fluoroamination[6] have been developed. Meanwhile, and the result showed that DCE was a suitable sol-
we also have developed some useful difunctionaliza- vent. Reaction in air led to a lower yield (entry 21).
tions of alkenes.[7] The energy-rich and flexible organ- Therefore, the optimized conditions are as follows:
ic azides are widely used in chemistry, biology, medi- using 10 mol% FeCl3 as the catalyst, TMSN3 as the
cine and materials.[8] For example, the Staudinger re- azido source, and DCE as the solvent at room tem-
action[9] as a ligation method for the conjugation of perature under argon.
biomolecules has been popular among bioorganic
With the optimized reaction conditions in hand, we
chemists.[10] The 1,3-dipolar cycloaddition of alkynes investigated the scope of alkenes and 1-(alkylthio)pyr-
with azides, an application of the Huisgen reaction in rolidine-2,5-diones. As shown in Table 2, both aromat-
the field of “click chemistry”, was widely investigat- ic and aliphatic alkenes were suitable substrates. For
ed.[11] Reactions of thioacids or thioesters with organic styrenes with different substituents on the phenyl
azides have been actively studied as a chemical liga- rings, their electronic effect was not evident, but the
tion method.[12] On the other hand, sulfides are impor- steric hindrance greatly affected their reactivity, and
tant building blocks in organic synthesis, materials sci- the substrates with substituents at ortho-sites provided
ence and the pharmaceutical industry.[13] To the best lower yields (see 3d, 3i and 3l). Several styrenes with
of our knowledge, azidoalkylthiation of alkenes has disubstituents on the C=C bonds were screened, and
been not reported. 1-(Alkylthio)pyrrolidine-2,5- they provided satisfactory yields (see 3n–r). Interest-
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Table 1. Optimization of reaction conditions for the three-
component coupling of styrene (1a), 1-(phenylthio)pyrroli-
dine-2,5-dione (2a) and trimethylsilyl azide.[a]
Scheme 1. Synthesis of 3a on a gram scale under the stan-
dard conditions.
Entry Catalyst
Azido
source
Solvent Time Yield
[h]
[%][b]
À
À
including C F bond (3f and 3w), C Cl bond (3g–
i and 3x–z), C Br bond (3j–l), CF3 (3m and 3aa) and
1
–
TMSN3
TMSN3
TMSN3
TMSN3
TMSN3
TMSN3
TMSN3
TMSN3
TMSN3
TMSN3
DMF
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
12
12
12
12
12
12
12
12
12
12
12
12
12
24
24
trace[c]
84
À
2
3
FeCl3
Cu(OAc)2
ethers (3v, 3ab, 3ac and 3ah).
trace
trace
trace
trace
trace
trace
35
22
45
37
13
A scale-up experiment was investigated using azi-
doarylthiation of 1a as the example (Scheme 1). Reac-
tion of 1a (10 mmol, 1.04 g), 2a (15 mmol, 3.11 g) and
trimethylsilyl azide (20 mmol, 2.3 g) under the stan-
dard conditions provided 3a in 68% yield (1.74 g).
Therefore, the present method is effective for the
scaled-up synthesis of b-alkyl sulfide azides.
4
CuI
5
6
7
8
Pd(OAc)2
BF3·Et2O
AgOAc
Fe2O3
9
FeS·7H2O
FeS
Fe2(SO4)3·H2O TMSN3
10
11
12
13
14
15
16
17
18
19
20
21
We explored the three-component reaction mecha-
nism. When a radical scavenger, 2,2,6,6-tetramethylpi-
peridinyl-1-oxyl (TEMPO), was added to system of
styrene (1a), 1-(phenylthio)pyrrolidine-2,5-dione (2a)
and trimethylsilyl azide, and the reaction did not
work, which indicated that the reaction could involve
in a free radical intermediate process. Electron spin
resonance (ESR) was applied to track the iron-cata-
lyzed reaction of 1a, 2a and TMS-N3 with 5,5-dimeth-
yl-1-pyrroline N-oxide (DMPO) as a radical trapping
agent, and the results showed that an N-centered radi-
cal was observed (see the Supporting Information for
details). Therefore, a plausible mechanism for the azi-
doalkylthiation of alkenes is proposed in Scheme 2.
One single electron transfer (SET) from sulfur in 1 to
Fe3+ gives radical cation I and Fe2+, and cleavage of
FeSO4
Fe(acac)3
FeCl3
FeCl3
FeCl3
FeCl3
FeCl3
FeCl3
FeCl3
FeCl3
TMSN3
TMSN3
NaN3
trace
trace
80
TsN3
TMSN3
TMSN3
TMSN3
TMSN3
TMSN3
TMSN3
CHCl3 12
MeCN 12
77
THF
12
46
EtOAc 12
toluene 12
DCM 12
70
17
63[d]
[a]
Reaction conditions: under argon atmosphere, 1a
(0.2 mmol), 2a (0.3 mmol), catalyst (0.02 mmol), azido
source (0.4 mmol), solvent (2.0 mL), temperature (room
temperature, ca. 258C), time (12 h). DCE=1,2-dichloro-
ethane.
Isolated yields.
Temperature (908C).
Under air.
[b]
[c]
[d]
À
N S bond in I provides cation II and radical III (the
N-centered radical was observed by ESR). Treatment
of III with Fe2+ regenerates the Fe3+ catalyst leaving
IV. Meanwhile, electrophilic addition of II to alkene
ingly, only anti-diastereomers were observed in the
1H NMR spectra for 1,2-disubstituted alkenes (see 3o,
3p, 3r and 3ae), and norbornene gave two diastereo-
mers (dr=2:1) (see 3af). The results indicated that
a three-membered cyclic thiiranium intermediate (V)
could occur during azidoalkylthiation of alkenes (see
reaction mechanism in Scheme 2). Next, various 1-(ar-
ylthio)pyrrolidine-2,5-diones (2) were attempted (see
3s–aa), and the substrates (2) containing electron-do-
nating groups on the phenyl rings exhibited higher re-
activity than those containing electron-withdrawing
groups. For aliphatic alkenes, they also afforded rea-
sonable yields (see 3ab–aj). We used 1-(alkylthio)pyr-
rolidine-2,5-diones as the sulfur source, and they also
gave satisfactory results (see 3ak–am). The present
Scheme 2. Possible mechanism for the iron-catalyzed azi-
method exhibited tolerance of some functional groups doalkylthiation of alkenes.
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Table 2. Substrate scope for the iron-catalyzed azidoalkylthiation.[a,b]
[a]
Reaction conditions: under argon atmosphere, 1 (0.2 mmol), 2 (0.3 mmol), FeCl3 (0.02 mmol), TMSN3
(0.4 mmol), DCE (2.0 mL), temperature (room temperature, ca. 258C), time (12 h) in a sealed Schlenk
tube.
Isolated yields.
[b]
(1) gives three-membered cyclic thiiranium intermedi- plied in the synthesis of other molecules. For instance,
ate V, and reaction of TMSN3 with VI in the presence b-amino sulfide 4a was easily prepared via reduction
of IV provides the target product (3) freeing IV-TMS. of (2-azido-2-phenylethyl)(phenyl)sulfane (3a) with
A similar process was reported in the previous stud- PPh3 and water[17] at room temperature. Copper-cata-
ies.[16]
lyzed coupling of 3a with phenylacetylene afforded
It is noteworthy that azido compounds are very the corresponding triazole (5a) in 68% yield
useful synthetic intermediates and they are often ap- (Scheme 3).
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7.41–7.34 (m, 3H), 7.33–7.27 (m, 4H), 7.23–7.19 (m, 1H),
7.17–7.15 (m, 2H), 4.57 (dd, J=8.0 Hz, J=6.0 Hz, 1H),
3.91(s, 2H), 2.90–2.80 (m, 4H), 2.78–2.73 (m, 2H); 13C NMR
(100 MHz, CDCl3): d=140.3, 138.6, 129.0, 128.8, 128.6,
127.0, 126.6, 66.6, 38.9, 36.4, 34.6; ESI-MS: m/z=284.3 [M+
H]+.
Acknowledgements
The authors wish to thank the National Natural Science
Foundation of China (Grant Nos. 21372139 and 21221062)
and Shenzhen Sci & Tech Bureau (CXB201104210014A) for
financial support.
Scheme 3. Applications of synthesized compound 3a.
In summary, we have developed a simple, efficient
and practical iron-catalyzed azidoalkylthiation of al-
kenes with the readily available 1-(alkylthio)pyrroli- References
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Experimental Section
General Procedure for Synthesis of Compounds 3a–
am
A 25-mL oven-dried Schlenk tube was charged with FeCl3
(0.02 mmol, 3.3 mg), and 1-(alkylthio)pyrrolidine-2,5-dione
(2) (0.3 mmol), dry 1,2-dichloroethane (2.0 mL), alkene
(0.2 mmol) and TMSN3 (0.4 mmol, 46 mg, 53 mL) were
added to the tube under an argon atmosphere. The tube was
sealed and the mixture was stirred at room temperature for
12 h. The resulting mixture was filtered through Celite, and
the filtrate was concentrated under vacuum. The residue
was purified by silica gel column chromatography using pe-
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(2-Azido-2-phenylethyl)(phenyl)sulfane (3a): Eluent: pe-
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(84%); colorless film; 1H NMR (600 MHz, CDCl3): d=
7.39–7.37 (m, 4H), 7.34 (t, J=7.3 Hz, 1H), 7.32–7.28 (m,
4H), 7.24 (t, J=7.3 Hz, 1H), 4.58 (t, J=7.1 Hz, 1H), 3.25
(d, J=7.1 Hz, 2H); 13C NMR (75 MHz, CDCl3): d=138.4,
135.2, 130.4, 129.2, 129.0, 128.8, 127.0, 126.9, 66.3, 41.0; ESI-
MS: m/z=256.2 [M+H]+.
(2-Azido-2-phenylethyl)(4-chlorophenyl)sulfane
(3x):
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6 Iron-Catalyzed Azidoalkylthiation of Alkenes with
Trimethylsilyl Azide and 1-(Alkylthio)pyrrolidine-2,5-diones
Adv. Synth. Catal. 2016, 358, 1 – 6
Jipan Yu, Min Jiang, Zhixuan Song, Tiancheng He,
Haijun Yang, Hua Fu*
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