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Accepted Article
Title: Alkyl Sulfides as Promising Sulfur Sources: Metal-Free Synthesis
of Aryl Alkyl Sulfides and Dialkyl Sulfides by Transalkylation of
Simple Sulfides with Alkyl Halides

Authors: Renhua Qiu, Ting Liu, Longzhi Zhu, Shuang-Feng Yin, Chak-
Tong Au, and Nobuaki Kambe

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Alkyl Sulfides as Promising Sulfur Sources: Metal-Free Synthesis

of Aryl Alkyl Sulfides and Dialkyl Sulfides by Transalkylation of
Simple Sulfides with Alkyl Halides
Ting Liu,[a] Renhua Qiu,*[a][b] Longzhi Zhu,[a] Shuang-Feng Yin,*[a] Chak-Tong Au,[c] Nobuaki Kambe*[a][b]
Abstract: A site-selective metal-free dealkylative approach to sulfide and labeled methyl iodide (Scheme 1c).[19a] Although one
synthesize aryl alkyl and symmetrical dialkyl sulfides was developed. example was known in the transalkylation of sulfides with alkyl
This procedure is convenient and has wide functional group halides,[19] we expected that thioethers having a methyl or a
tolerance giving rise to sulfides carrying various alkyl chains in good simple alkyl substituent(s) can serve as useful sulfur sources of
to excellent yields from simple alkyl sulfides and alkyl halides. This heavier alkyl sulfides and that this metal-free transalkylation

Accepted Manuscript
transalkylation proceeds by an ionic mechanism via sulfonium reaction can be a convenient route for synthesizing alkyl sulfides
intermediates and it was proposed that DMAC may participate in via C–S bond cleavage. Herein, we present a site-selective
part to promote the reaction. metal-free dealkylative approach for the synthesis of aryl alkyl
and dialkyl sulfides from simple alkyl sulfides and alkyl halides
under ambient air conditions (Scheme 1d).
Alkyl sulfides have received considerable attention as
important scaffolds in natural products, [1] material chemistry,[2] Scheme 1. Site-Selective C(sp3) –S Bond Cleavage
pharmaceuticals,[3] food chemistry[4] and ligands.[5] The synthesis
of sulfides with a saturated carbon skeleton receives increasing
attention,[6] especially in pharmaceutical areas, due in part to
higher hydrophilic nature of alkyl groups than aromatic
groups.[6d-f] Conventional approaches for alkyl-sulfur bond
formation are mainly based on substitution reactions of
nucleophilic sulfur reagents such as metal sulfides, [7]
thiosulfates,[8] thiourea,[9] thiol derivatives[10] with electrophilic
alkylating reagents. The reactions of inverse polarity, i. e.
between electrophilic sulfuration reagents such as sulfenyl
halides,[11] or disulfides[12] and alkyl nucleophiles or olefins also
make convenient routes. Radical reactions also provide useful
methods for alkyl sulfide synthesis.[13] Transition metal catalysts
provide powerful tools for constructing (sp2)C–S bond
formation[14] by coupling[15] or addition reactions,[16] but their
application to (sp3)C–S bond formation is largely limited due to
the facile β-hydrogen elimination.[15d] Table 1. Optimization of Reaction Conditions[a]

These C–S bond forming reactions mentioned above are

mostly based on cleavage of sulfur-hydrogen or sulfur-
heteroatom bonds. Recently, transition metal catalyzed Ar–S
bond forming reactions with C–S bond cleavage were reported
as shown in Scheme 1. Mao reported palladium-catalyzed
debenzylative approach to generate diarylsulfides (Scheme
1a).[17] Schmink also synthesized diarylsulfides by treatment of
phenyl alkenyl sulfide with phenyl halides catalyzed by a
Pd/Xantphos system (Scheme 1b).[18] As a successful example
of metal-free formation of sulfur-alkyl bonds via C–S bond
cleavage, Rapoport reported the direct reaction of tritium-labeled
methyl phenyl sulfide with benzyl iodide to form phenyl benzyl

[a] T. Liu, Prof. R.H. Qiu, L.Z. Zhu, Prof. S.-F. Yin, Prof. N. Kambe
State Key Laboratory of Chemo/Biosensing and Chemometrics,
College of Chemistry and Chemical Engineering
Hunan University
Changsha, 410081, Hunan Province, China [a] 1a (0.3 mmol, 1.0 equiv), 12 h, isolated yields. [b] vacuum (ca. 0.1 MPa)
E-mail: renhuaqiu@hnu.edu.cn (R.Q.). sf_yin@hnu.edu.cn (S.Y.) and 2 equiv of 2a was used.
[b] Prof. N. Kambe
Department of Applied Chemistry, Graduate School of Engineering, We examined transalkylation of thioanisole (1a) with 2-
Osaka University, Suita, Osaka, 565-0871, Japan bromobenzyl bromide (2a) to give 3aa. (Table 1) During using
E-mail: kambe@chem.eng.osaka-u.ac.jp. (N.K.) various additives and catalysts (see Supporting Information),.
[c] Prof. C.T. Au
College of Chemistry and Chemical Engineering, Hunan Institute of
Surprisingly, we found that the reaction did not require any
Engineering, Xiangtan, Hunan, China additives or catalysts. Among the solvents examined (i.e.,

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DMSO, DMF, toluene), dimethylacetamide (DMAC) was found to
give the highest yield (entries 2−4). When the loading of 2-
bromobenzyl bromide was increased from 1 to 4 equiv, the yield
of 3aa increased gradually up to 94% (entries 1, 5−7). Although
this reaction proceeded at lower temperatures (25 °C to 140 °C),
the best yield was achieved at 160 °C (entries 7−12). This
reaction was completed in 4 h at 160 °C as shown in entries 13
to 17 (1 h, 73%; 4 h, 92%). However, in order to ensure reaction
completion, we conducted this reaction at 160 °C for 12 h
employing 1 equiv of alkylsulfide (1), 4 equiv of alkyl halide (2)
and DMAC as the solvent all though this study unless otherwise
stated.
[a]
Scheme 2. Substrates Scope of Alkyl Halides
[a] 1a (0.3 mmol, 1.0 equiv), 12 h, isolated yields. [b] 6 h. [c] 24 h. [d] 48 h. [e]
LiI (4.0 equiv).
We then employed various alkyl halides and conducted the
reaction with thioanisole (1a) as the PhS source in order to
examine the scope of the alkylating reagents (Scheme 2).
Benzyl bromides having a F, Cl, Br substituent at the ortho-,
meta- or para-position afforded the corresponding benzyl phenyl
sulfides 3aa−3cc in 74-94% yields. Unsubstutited benzyl phenyl
sulfide (3d) and 1,5-disubstituted product (3e) were obtained in
69% and 91%, respectively. Introduction of electron-withdrawing
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10.1002/asia.201801679
functionalyties such as 4-nitro (3f), 4-trifluoromethyl (3g), and 4-
cyano (3h) groups led to high yields, 87%, 85% (3gc, 60%), and
84%, respectively. Benzyl halides bearing an electron-donating
group, such as 4-tert-butyl and 4-methyl, also worked well to
give 3i (3ic) and 3j (3jc), albeit in somewhat lower yields, 68%
(40%) and 66% (45%) respectively. Sulfides containing a
biphenyl (3k), naphthalene (3l), sterically hindered
diphenylmethyl (3m) moiety were obtained in 82%, 48% and
60% yield, respectively. Benzyl chlorides can also be used in
place of benzyl bromides to give 3aa, g, i, j in satisfactory yields.
It is noteworthy that unactivated alkyl bromides and iodides were
also successfully employed to afford the corresponding alkyl
phenyl sulfides having a longer saturated carbon chain (3n−t) in
Accepted Manuscript
good yields. However, unactivated alkyl chlorides are less
reactive resulting in poor yields under identical reaction
conditions.
Scheme 3. Substrates Scope of Sulfides[a]
[a] 1 (0.3 mmol, 1.0 equiv), 12 h, isolated yields. [b] 1 h. [c] vacuum (ca. 0.1
MPa) and 2 equiv of 2a was used.
We then turned our attention to investigate the scope of
sulfides as the sulfur source in the reaction with benzyl bromide
2a (Scheme 3). Firstly, we examined the reaction of thioanisoles
having a various substituent (F, Cl, Br, OMe, Me) on the
aromatic ring. There was no significant effect of halogens at the
ortho, meta, and para positions, and the reactions gave the
corresponding products 4aa−4cb in 67-88% yields. Electron-
donating substituents (OMe, Me) did not affect the reaction to
give 4d and 4e in good yields (78% and 84%). Naphthyl and
heteroaryl sulfides 4f and 4g were obtained in 74% and 51%
yield, respectively. Regarding the alkyl group of the sulfur source
1, ethyl phenyl sulfide (1d) worked well giving rise to 3aa in 94%
yield. Interestingly, chloromethyl and vinyl sulfides (1b and 1c)
also served as a sulfur source to give 3aa in 88% and 70%
yields, respectively. In order to examine the relative reactivities
of 1b-d, reactions were conducted separately and quenched at
an early stage (1 h). From the yields of 3aa (Scheme 3), it was
suggested that the reactivity of alkyl phenyl sulfides decreased
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in the order 1a(Me) > 1d(Et) > 1b(CH2Cl) > 1c(vinyl).
To our delight, symmetrical and unsymmetrical dialkyl sulfides
1e−l worked smoothly as the sulfur source and afforded
symmetrical dibenzyl sulfide 4h in moderate yields. The results
that the similar control experiments conducted for only 1 h
afforded 4h in nearly the same yields suggest that structures of
alkyl groups on the sulfur atom of 1e−l exert little effect on the
reaction rate. In these reactions using dialkyl sulfides 1e−l and
benzyl bromide 2a, alkyl benzyl sulfides were expected to be
formed as the intermediates. However, only small peaks
assignable to such intermediates carrying only one benzyl group
were detected by GC-MS analysis, indicating that the reaction
was complete under the conditions employed.
When benzyl halides bearing various functional groups were
allowed to react with allyl methyl sulfide 1l, the corresponding
symmetrical dibenzyl sulfides (4h−n) were obtained in moderate
to good yields (Scheme 4). Notably, unactivated alkyl iodides
also reacted under the same reaction conditions to give 4o and
4p. Unfortunately, any attempts to prepare unsymmetrical
sulfides by stepwise substitution of allyl and methyl groups of 1l
failed resulting in double substitution to give 4.
Scheme 4. Double Transalkylation of Allyl(methyl)sulfane with Halides[a]
[a] 1l (0.3 mmol, 1.0 equiv), 12 h, isolated yields. [b] 2 was 3-iodo-1-
phenylpropane. [c] 2 was 1-iodohexane.
When thioanisols bearing a hydroxyl group were subjected to
the present transalkylation with benzyl bromides or an alkyl
iodide, phenol acetylation took place concomitantly to give 5a-f
in good yields (Scheme 5). Since alkylation at the phenoxy
group was completely suppressed and acetyl group can easily
be removed to regenerate phenoxy group,[20] the present
reaction can be applicable to preparation of phenols bearing an
alkylthiol group.
Scheme 5. Transalkylation of Thioanisole Bearing Hydroxyl Group[a]
[a] 1 (0.3 mmol, 1.0 equiv), 12 h, isolated yields. [b] 2 was 3-iodo-1-
phenylpropane.
To demonstrate the potential application of this approach, we
coupled thioanisole (1a, 5.0 mmol) with (2-
bromobenzyl)(phenyl)sulfane, generating 3aa in 87% yield at
gram scale (1.2 g, 4.3 mmol). The corresponding product 3aa
was isolated in 87% in pure form after column chromatography
on silica gel (Scheme 6). For furthermore manipulation of the
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10.1002/asia.201801679
product, 3aa was subjected to alkynylation, phenylation,
phenoxylation, and sulfonylation according to previous report,[21]
and the desired products 6, 7, 8 and 9 were obtained in 84%,
91%, 88% and 82% yield, respectively.
Control experiments were performed using 1a and 2a to shed
light on the reaction pathway (Scheme 7). When DMAC, N,N-
dimethylformamide, diethylacetamide or N-acetylmorpholine
were used as the solvent, 3aa was obtained in 94%, 87%, 86%
and 64%, respectively (Scheme 7a), indicating that the various
amides can be used as the solvent although DMAC gave the
best yield. When the reaction was conducted using toluene as a
non-polar solvent, the yield decreased to 50%. However,
interestingly, the yield increased when DMAC was added in
small amounts. As shown in the graph in Scheme 7a, higher
yields were achieved as more DMAC was added, reaching up to
Accepted Manuscript
91% using 6 equiv. of DMAC. These results suggest that DMAC
accelerates the reaction not only as the solvent but also as a
reagent to promote the reaction. The evidence that the reaction
was not quenched by addition of radical inhibitors, 2,6-di-tert-
butyl-4-methylphenol (BHT), (2,2,6,6-tetramethyl-piperidin-1-
yl)oxidanyl (TEMPO) or 1,4-benzoquinone (1,4-BQ) ruled out
radical mechanisms (Scheme 7b). When the reaction was
conducted using different amounts of benzyl bromide 2a, the
yield increased as the amount of 2a increased (Scheme 7c),
suggesting that 2a may be involved in the rate determining step.
Scheme 6. Gram Scale Synthesis and Applications
Scheme 7. Control Experiments
On the basis of the results of the control experiments,[19] we
proposed possible pathways of this transalkylation (Scheme 8).
The halide 2a reacted with 1a through the nucleophilic
substitution to produce a sulfonium intermediate I. Next, alkyl
bromide was removed to generate 3aa via a direct nucleophilic
attack by Br anion. As a competing process, DMAC may attack
the alkyl carbon on the intermediate I to form an ammonium or
iminonium intermediate II to promote the reaction.
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Scheme 8. Possible Mechanism
In summary, we reported a convenient metal-free dealkylative
approach to generate aryl alkyl or symmetrical dialkyl sulfides
from simple alkyl sulfides and alkyl halides. A variety of alkyl
sulfides bearing a various functional group(s) were synthesized
in good yields. This transalkylation proceed in an ionic
mechanism via sulfonium intermediates and it was suggested
that DMAC may participate in the second step to promoted the
reaction.
Experimental Section
To a 10 mL screw capped vial equipped with a magnetic stirring bar was
added sulfide (1) (0.3 mmol), halides (2) (1.2 mmol), and DMAC (1.0 mL)
under air atmosphere. The reaction mixture was placed in a preheated oil
bath at 160 °C and vigorously stirred for 12 h. Subsequently it was
cooled down to room temperature, filtered through a plug of celite and
then washed with saturated brine and extracted by ethyl acetate (3 × 5.0
mL). The solvents were removed under reduced pressure and the crude
reaction mixture was purified by chromatography on silica gel using
PE/EtOAc as eluent to obtain the desired product 3, 4 or 5.
Acknowledgements
The authors thank the Natural Science Foundation of China (Nos.
21676076, 21725602, 21878071), Recruitment Program for Foreign
Experts of China (WQ20164300353) and Hu-Xiang High Talent of Hunan
Province (2016RS3023, 2018RS3042).
Keywords: Alkyl Sulfides • Alkyl Halides • Transalkylation •
Metal-free
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Ting Liu, Renhua Qiu,* Longzhi Zhu,

Shuang-Feng Yin,* Chak-Tong Au,
Nobuaki Kambe*

Page No. – Page No.

Alkyl Sulfides as Promising Sulfur

Accepted Manuscript
Sources: Metal-Free Synthesis of Aryl

Alkyl Sulfides and Dialkyl Sulfides by

Transalkylation of Simple Sulfides

with Alkyl Halides

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