One-pot preparation of Julia-Kocienski sulfides and sulfones from alcohols

Article abstract of DOI:10.1016/j.tetlet.2019.151017

A method for one-pot preparation of Julia-Kocienski sulfides and sulfones from alcohols and thiols is reported. A variety of primary alcohols were converted to the corresponding mesylates by methansulfonyl chloride and triethylamine in THF. After the reaction is complete, thiol (1 or 10) and either NaH or t-BuOK were added. The Julia-Kocienski sulfides 3, 9 and 11 were prepared by one-pot two steps procedure from alcohols in 76–96% yields (16 examples). Furthermore, after the sulfide formation, the reaction mixture was neutralized by p-toluenesulfonic acid and treated with H₂O₂ and ammonium molybdate in EtOH to give the Julia-Kocienski sulfones 4 in good yields except for trans-2-hexen-1-ol.

Full text of DOI:10.1016/j.tetlet.2019.151017

Journal Pre-Proof
One-pot preparation of Julia-Kocienski sulfides and sulfones from alcohols
Kaori Ando, Junichiro Hattori
PII:
S0040-4039(19)30774-9
DOI:
https://doi.org/10.1016/j.tetlet.2019.151017
TETL 151017
Reference:
Tetrahedron Letters
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Revised Date:
Accepted Date:
26 June 2019
31 July 2019
2 August 2019
Please cite this article as: Ando, K., Hattori, J., One-pot preparation of Julia-Kocienski sulfides and sulfones from
alcohols, Tetrahedron Letters (2019), doi: https://doi.org/10.1016/j.tetlet.2019.151017
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JOURNAL PRE-PROOF
Tetrahedron Letters
One-pot preparation of Julia-Kocienski sulfides and sulfones from alcohols
Kaori Ando, Junichiro Hattori
aDepartment of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Yanagido 1-1, Gifu 501-1193, Japan
ARTICLE INFO
ABSTRACT
Article history:
Received
Received in revised form
Accepted
A method for one-pot preparation of Julia-Kocienski sulfides and sulfones from alcohols and
thiols is reported. A variety of primary alcohols were converted to the corresponding mesylates
by methansulfonyl chloride and triethylamine in THF. After the reaction is complete, thiol (1 or
10) and either NaH or t-BuOK were added. The Julia-Kocienski sulfides 3, 9 and 11 were
prepared by one-pot two steps procedure from alcohols in 76-96% yields (16 examples).
Furthermore, after the sulfide formation, the reaction mixture was neutralized by p-
toluenesulfonic acid and treated with H2O2 and ammonium molybdate in EtOH to give the Julia-
Kocienski sulfones 4 in good yields except for trans-2-hexen-1-ol.
Available online
Keywords:
Julia-Kocienski reagents
One-pot reaction
2019 Elsevier Ltd. All rights reserved.
Sulfides from alcohols
Sulfones from alcohols
The Julia-Kocienski reaction is a very strong tool for the
synthesis of E-alkenes from carbonyl compounds and
5
heteroaryl sulfones such as 4 and used extensively in the last
decade for the construction of carbon-carbon double bonds
present in many natural products (Scheme 1).1,2 When the
sulfone reagents 4 are prepared from thiol 1 and alcohols 2, the
corresponding sulfides 3 are generally prepared by Mitsunobu
reaction3 using either DEAD or DIAD along with Ph3P.2b
However, both DEAD and DIAD are expensive and the
byproducts (Ph3P=O and (NHCO2R)2) are often difficult to be
removed from the desired product.4 Several approaches similar
to Mitsunobu reaction were reported5 and Lewis acid catalyzed
C-S bond formations were also developed.6 However, some are
restricted to benzylic and allylic alcohols and some have similar
problems as Mitsunobu reaction does. Since alcohols can be
easily transformed to alkyl halides and sulfonates which can be
used for alkylation of thiol, sulfides can be prepared by these two
steps. In fact, some Julia-Kocienski reagents were prepared by
these two steps followed by oxidation.7 Although Bonini and co-
workers reported that the one-pot preparation of propargylic
sulfides via either iodide formation or tosylate formation, the
yields were not always good.8 One-pot reactions, where a
number of transformations are carried out in a single pot, have
attracted considerable attention because they offer significant
advantages such as elimination of purification steps, reduction of
wastes, time, and costs, and increase efficiency of the process.9,10
Now one-pot synthesis is one of the most powerful synthetic
strategies for the environmentally benign reactions. Therefore,
we studied one-pot preparation of Julia-Kocienski sulfides and
sulfones from alcohols and thiols. Since halogenation reactions
are generally performed under acidic conditions, we chose
mesylate formation from alcohols followed by their reaction with
1 under basic conditions according to Scheme 2. Herein we
would like to report our results.
The mesylation reaction of n-pentanol 2a was carried out by
treating with methansulfonyl chloride (1.2 eq) and triethylamine
(1.3 eq) in THF for 3 h to give mesylate 6a in 92% yield
(Scheme 3). The yield of 6a did not much change by shortening
the reaction time to 1 h and 6a was obtained in 90% yield. The
———
 Kaori Ando. Tel.: +81-58-293-2674; e-mail: ando@gifu-u.ac.jp

JOURNAL PRE-PROOF
2
Tetrahedron
obtained mesylate 6a was used for alkylation reaction of thiol 1.
Table 1. One-pot preparation of the Julia-Kocienski sulfides 3 from
The Julia-Kocienski sulfide 3a was obtained in 86% yield when 1
was deprotonated with NaH (1.2 eq) in THF followed by the
treatment with 6a (1 eq) for 24 h. When t-BuOK (1.2eq) was
used instead of NaH, 94% yield of 3a was obtained. Thus, the
sulfide formation can be carried out using either NaH or t-BuOK
in THF.
alcohols.
entry
2
time
Base (eq)
conditions
yield
1
2
3b
2a
2a
2a
2b
2b
2c
2c
2c
2c
1.5 h
1.5 h
1.5 h
2.5 h
2.5 h
1 h
NaH (2.3)
NaH (2.3)
rt, 16 h
86%
64%
83%
75%
90%
60%
67%
57%
83%
reflux, 2 h
rt, 16 h
NaH (2.3)
4
NaH (2.3)
50 °C, 9 h
50 °C, 21 h
50 °C, 15 h
50 °C, 15 h
50 °C, 15 h
reflux, 6 h
5c
6
7d
8e
9
NaH (2.3)
NaH (2.6)
1 h
t-BuOK (2.5)
t-BuOK (2.5)
t-BuOK (2.5)
1 h
1 h
a) A mixture of 1 and base was added unless otherwise noted. b) Base
was added after the addition of 1. c) 1.3 eq of 1 was used. d) 1 wad added
after the addition of base. e) THF:DMF = 3.5:1.5.
We next explored the possibility of sequential one-pot
preparation of the Julia-Kocienski sulfide 3 (Table 1). After n-
pentanol 2a was treated with methansulfonyl chloride (1.2 eq)
and triethylamine (1.3 eq) in THF for 1.5 h, a mixture of 1 (1 eq)
and NaH (2.3 eq) in THF was added to the above reaction
mixture. The resulting mixture was stirred for 16 h to give
sulfide 3a in 86% yield,11 which is higher than the yield obtained
from mesylation (92%) and alkylation of 1 using NaH (86%)
(92% x 86% = 79%) (entry 1). When alkylation of 1 was
performed at higher temperature (50 °C to reflux), the yield
dropped to 64% due to partial decomposition of mesylate 6a
(entry 2). When NaH was added after the addition of 1 for easier
operation, 3a was obtained in a comparable yield to entry 1 (83%,
entry 3). The scope of this reaction was next explored with two
other types of alcohols. Although the alkylation of 1 with the
mesylate derived from -branched citronellol 2b hardly
proceeded at room temperature, the reaction at 50 °C gave 3b in
90% yield using 1.3 eq of 1 (entry 5). The alkylation of 1 with
the mesylate derived from -branched cyclohexylmethanol 2c
was slow even at 50 °C to give 3c in 60% yield (entry 6). The
yield increased to 67% by using t-BuOK (entry 7) and 83% yield
was obtained when the mixture was heated under reflux for 6 h
(entry 9). The addition of DMF to the THF solution decreased
the yield of 3c (entry 8).
Having optimized the reaction conditions, we next focused
our attention on the reaction of the alcohols having functional
groups in this one-pot two steps procedure (Table 2). When the
alcohol 2d having a t-BuMe2SiO group was transformed to its
mesylate and then treated with 1 and NaH at 50 °C, 84% yield of
sulfide 3d was obtained (entry 1). Although the yield of sulfide
3e was only 56% when 6-tetrahydropyranyloxyhexan-1-ol 2e
was treated in a similar manner as entry 1, the yield improved to
87% under reflux (entries 2-3). Tetrahydro-2-furanmethanol 2f
was converted to sulfide 3f in 74% yield using t-BuOK by
following the procedure of entry 9 in Table 1 (entry 4). Using
1.3 eq of 1, the yield was slightly improved to 76% (entry 5).
The alcohol 2g having a -unsaturated ester group was also
transformed to sulfide 3g in 69% yield using NaH (entry 6). The
yield was lowered to 46% by using t-BuOK and was improved to
86% using 1.3 eq of 1 under reflux (entries 7-9). Both trans-2-
hexen-1-ol 2h and cis-2-hexen-1-ol 2i were transformed to the
allyl mesylates, which reacted with the anion derived from 1 and
NaH smoothly. The sulfides 3h and 3i were obtained in 88% and
89% yield, respectively, without isomerization after 3-5 h at
Table 2. One-pot preparation of sulfides 3 from alcohols having
functional groups.
entry
2
base (eq)
conditions
yield
1
2
2d
2e
2e
2f
NaH (2.3)
NaH (2.3)
NaH (2.3)
t-BuOK (2.5)
t-BuOK (2.8)
NaH (2.3)
t-BuOK (2.5)
NaH (2.3)
NaH (2.6)
NaH (2.3)
NaH (2.3)
NaH (2.3)
NaH (2.3)
NaH (2.3)
50 °C, 7.5 h
50 °C, 7 h
reflux, 7 h
reflux, 19 h
reflux, 19 h
50 °C, 5 h
50 °C, 5 h
reflux, 5.5 h
reflux, 6.5 h
rt, 5 h
84%
56%
87%
74%
76%
69%
46%
75%
86%
88%
89%
95%
91%
96%
3
4
5a
2f
6
2g
2g
2g
2g
2h
2i
7
8
9a
10
11
12
13
14
rt, 3 h
2j
rt, 2 h
2k
2l
rt, 2 h
rt, 2 h
a: 1.3 eq of 1 was used.

JOURNAL PRE-PROOF
Table 3. One-pot preparation of 1,3-benzothiazol-2-yl sulfides 11
from alcohols.
room temperature (entries 10-11). The mesylates derived from
benzyl alcohols 2j-2l are also highly reactive and the
corresponding sulfides were obtained in 91-96% yield by the
reaction using NaH at room temperature (entries 12-14).
Nicolaou and co-workers reported a total synthesis of
Artochamins H, I, and J, which are isolated from Artocarpus
chama as cytotoxic ingredients.12 In their synthesis, they used
the Julia-Kocienski reaction of sulfone 9, followed by [3,3]
Claisen rearrangement, decarboxylation, and [2,2] cycloaddition
(Scheme 4). The alcohol 7 was transformed to the sulfide 8 by
Mitsunobu reaction using DEAD and Ph3P in 77% yield and then
8 was oxidized by H2O2 and ammonium molybdate to give the
sulfone 9. We applied our one-pot two steps procedure to the
preparation of 8 from 7. After 7 was treated with methansulfonyl
chloride and triethylamine in THF for 1 h, a THF solution of 1
and NaH was added and stirred at room temperature for 2 h. The
sulfide 8 was obtained in 95% yield. Our one-pot two steps
procedure has an advantage over Mitsunobu reaction in high
yield, simple work-up and low cost of the reagents.
entry
2
base (eq)
conditions
yield
1
2
3
4
5
6
2a
2a
2c
2j
2j
2j
NaH (2.3)
t-BuOK (2.5)
t-BuOK (2.5)
NaH (2.3)
rt, 22 h
rt, 22 h
62%
83%
88%
78%
79%
91%
reflux, 6.5 h
rt, 2 h
t-BuOK (2.5)
NaH (2.3)
rt, 2 h
50 °C, 2 h
61% yield. The sulfide derived from cis-2-hexen-1-ol 2i
(cis:trans =97.5:2.5) was also oxidized to the corresponding
sulfone 4i. Oxidation occurred rapidly and the yield was 83%,
but the obtained sulfone was a mixture of cis:trans = 78:22.
Unfortunately, the isomerization was further promoted when
Na2WO47b was used instead of ammonium molybdate (cis:trans =
27:73, 39% yield). This could be explained by the lower Lewis
acidity of Mo(6+) compared to W(6+).15 The benzyl sulfide was
oxidized to 4j in 83% yield.
Finally, we explored the possibility of one-pot preparation of
the Julia-Kocienski sulfones 4 from alcohols via mesylates and
sulfides (Table 4). After n-pentanol 2a was treated with
methansulfonyl chloride and triethylamine in THF for 1 h, 1 and
NaH was added and stirred for 21 h. Then ethanol, aq. H2O2 (9
eq), and ammonium molybdate (0.1 eq) were added and the
resulting mixture was stirred for 23 h to give 4a in 69% yield
(entry 1). This yield of our one-pot three-steps procedure from
2a to 4a was lower than that of three separate reactions (92%
(mesylation) x 86% (alkylation using NaH) x 97% (oxidation) =
77%). After alkylation of thiol 1 was completed, the reaction
mixture was concentrated under reduce pressure in order to
remove THF solvent and the residue was treated in a similar
manner as entry 1. Disappointingly, slightly lower 63% yield
was obtained (entry 2). When ammonium molybdate was
replaced with Na2WO4, only the sulfide 3a was obtained in 42%
yield instead of the desired 4a (entry 3). When oxone
(2KHSO5·KHSO4·K2SO4) was used as an oxidant, 4a was
obtained in 67% yield after 17 h (entry 4). We next turned our
attention to the pH of the reaction mixture. The pH of the
oxidation reaction mixture (Scheme 5) was 3, while the final pH
in the one-pot three steps procedure was 10 (entry 1 in Table 4).
Neutralization may be necessary prior to the oxidation step. We
One-pot two steps procedure was applied for the preparation
of the 1,3-benzothiazol-2-yl sulfides 11. After an alcohol was
treated with methansulfonyl chloride and triethylamine in THF,
10 (1.0 eq) and base were added (Table 3). When n-pentanol 2a
was transformed to its mesylate and then treated with 10 and
NaH (2.3 eq) at room temperature, sulfide 11a was obtained in
62% yield (entry 1). Using t-BuOK (2.5 eq) instead of NaH, the
yield increased to 83% (entry 2).
The reaction of
cyclohexylmethanol 2c was carried out using t-BuOK under
reflux to give 11c in 88% yield (entry 3). Benzyl alcohol 2j was
transformed to sulfide 11j at room temperature in 78 and 79%
yield using NaH and t-BuOK, respectively (entries 4-5). At 50
°C for 2 h, the yield increased to 91% (entry 6). Thus, 1,3-
benzothiazol-2-yl sulfides 11 were prepared in high yield by the
one-pot procedure from alcohols.
The obtained sulfides 3 were next oxidized to the
corresponding sulfones 4 (Scheme 5). When 3a (R = n-Bu) was
oxidized by 35% H2O2 aq. (9 eq) and ammonium molybdate13
(0.1 eq) in ethanol, sulfone 4a was obtained in 97% yield. In a
similar manner, the sulfide derived from trans-2-hexen-1-ol 2h
(trans only) was oxidized to 4h as a trans:cis = 96:4 mixture in

JOURNAL PRE-PROOF
4
Tetrahedron
Table 4. One-pot three steps procedure from 2a to the sulfone 4a.
A typical one-pot preparation of sulfide 3 (entry 1 in Table 1)
To a solution of n-pentanol (0.440 g, 5.0 mmol) in THF (20.0
mL) at 0 °C were added methansulfonyl chloride (0.465 mL, 6.0
mmol) and triethylamine (0.906 mL, 6.5 mmol). After the
mixture was stirred at RT for 1.5 h, a solution of 5-mercapto-1-
phenyl-1H-tetrazole (0.891 g, 5.0 mmol) and NaH (0.46 g, 11.5
mmol) in THF (5.0 mL) was added at 0 °C. The resulting mixture
was stirred at RT for 16 h. The reaction was quenched with sat.
NH4Cl aq., and the mixture was extracted with AcOEt (3 × 10
mL). The combined extracts were washed with brine, dried
(MgSO4), and concentrated under reduced pressure. The residue
was purified by silica gel column chromatography (hex:AcOEt =
entry time1
oxidant (eq)a
solvent
time2 yield
1
2
3
4
21 h
21 h
22 h
19 h
H2O2 (9)-A
H2O2 (9)-A
H2O2 (9)-B
Oxone (3)
EtOH
EtOH
23 h
23 h
24 h
17 h
69%
63%
0c
MeOH
1
8:1) to afford 3a (1.076 g, 86%) as a colorless oil. H NMR (400
MeOH-H2O
67%
MHz, CDCl3)  0.91 (3H, t, J = 7.3 Hz), 1.31-1.47 (4H, m), 1.83
(2H, quin, J = 7.3 Hz), 3.40 (2H, t, J = 7.3 Hz), 7.51-7.61 (5H,
m).15
a) A: (NH4)6Mo7O24 (0.1 eq), B: Na2WO4 (0.1 eq). b) The volatile
was removed under reduced pressure before the oxidation step. c)
Sulfide 3 was obtained in 42% yield.
A typical one-pot preparation of sulfone 4 (entry 3 in Table 5)
To a solution of benzyl alcohol (0.108 g, 1.0 mmol) in THF (3.0
mL) at 0 °C were added methansulfonyl chloride (0.93 mL, 1.2
mmol) and triethylamine (0.180 mL, 1.3 mmol). After the
mixture was stirred at RT for 1 h, a solution of 5-mercapto-1-
phenyl-1H-tetrazole (0.178 g, 1.0 mmol) and NaH (0.092 g, 2.3
mmol) in THF (2.0 mL) was added at 0 °C. The resulting mixture
was stirred at RT for 1 h and treated with p-TsOH·H2O (0.095 g,
0.5 mmol) for 15 min. EtOH (3.0 mL), (NH4)6Mo7O24·H2O
(0.123 mg, 0.1 mmol), and 34.5% aq. H2O2 (0.799 mL, 9.0
mmol) were added at 0 °C and the mixture was stirred at RT for
20 h. The reaction was quenched with sat. aq. Na2SO3, and the
mixture was extracted with AcOEt (2 × 8 mL). The combined
extracts were washed with brine, dried (MgSO4), and
concentrated under reduced pressure. The residue was purified by
silica gel column chromatography (hex:AcOEt = 5:1) to afford 4j
(0.246 g, 82%) as a colorless solid. mp = 101-102 °C
searched various acids for neutralization using the conditions of
entry 1 in Table 4. The yield of sulfone 4a was as follows: 0%
with 1M HCl, 1M NH4Cl, H2SO4, or HNO3, 70% with AcOH,
and 84% with p-TsOH·H2O. After the sulfide formation from n-
pentanol 2a was completed, the reaction mixture was neutralized
by p-TsOH·H2O (0.5 eq), and then ethanol, 35% H2O2 aq. (9 eq),
and (NH4)6Mo7O24·H2O (0.1 eq) were added to the reaction
mixture and stirred for 24 h. The sulfone 4a was obtained in
84% yield, which was higher than both the yield obtained from
three separate reactions (77%) and the yield obtained from the
one-pot sulfide formation and oxidation reaction (86% x 97% =
83%) (entry 1 in Table 5). In a similar manner, trans-2-hexen-1-
ol 2h was transformed to the sulfone 4h (entry 2). The yield was
only 35%16 and this transformation is better to be carried out by
the one-pot sulfide formation followed by the oxidation (84% x
61% = 51%). The reaction of benzyl alcohol 2j was also carried
out to give the sulfone 4j in 82% yield, which is higher than the
yield obtained from the one-pot sulfide formation and oxidation
reaction (95% x 83% = 79%) (entry 3).
1
(recrystallized from hexane-CH2Cl2 (5:1)); H NMR (400 MHz,
CDCl3)  4.93 (2H, s), 7.36-7.58 (10H, m).17
Acknowledgments
This research was partially supported by the JSPS KAKENHI
Grant Number 17K05781.
Table 5. One-pot three steps procedure from 2 to sulfone 4.
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2
3
2a
2h
2j
24 h
4 h
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19 h
20 h
84%
35%
82%
1 h
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In summary, we developed a method for the one-pot
preparation of the Julia-Kocienski sulfides and sulfones from
alcohols. After a variety of alcohols were transformed to the
mesylates by methansulfonyl chloride and triethylamine in THF,
thiol (1 or 10) and either NaH or t-BuOK were added. The Julia-
Kocienski sulfides 3, 9 and 11 were prepared from alcohols in
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132 (2010) 11045
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3765.
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separately reported allyl sulfones were prepared in only low yield by the
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JOURNAL PRE-PROOF
6
Tetrahedron
Highlights
 One-pot reaction
 Preparation of Julia-Kocienski sulfides
from alcohols.
 Preparation of Julia-Kocienski sulfones
from alcohols.
 Useful for alkene synthesis

JOURNAL PRE-PROOF
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One-pot preparation of Julia-Kocienski
sulfides and sulfones from alcohols
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Kaori Ando, Junichiro Hattori
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