The thiolation of pentafluorobenzene with disulfides by C-H, C-F bond activation and C-S bond formation

Article abstract of DOI:10.1039/c7ob02836a

A metal-free thiolation reaction between pentafluorobenzene and disulfides by C-H, C-F bond activation and C-S bond formation is reported. Bisthiolated tetrafluorobenzene derivatives would be prepared in moderate to good yields from pentafluorobenzene and disulfides under mild conditions. A possible mechanism for the reaction was given.

Full text of DOI:10.1039/c7ob02836a

View Article Online
View Journal
Organic &
Biomolecular
Chemistry
Accepted Manuscript
This article can be cited before page numbers have been issued, to do this please use: Z. Liu, K. Ouyang
and N. Yang, Org. Biomol. Chem., 2018, DOI: 10.1039/C7OB02836A.
This is an Accepted Manuscript, which has been through the
Volume 14 Number
1 7 January 2016 Pages 1–372
Royal Society of Chemistry peer review process and has been
accepted for publication.
Organic &
Biomolecular
Chemistry
www.rsc.org/obc
Accepted Manuscripts are published online shortly after
acceptance, before technical editing, formatting and proof reading.
Using this free service, authors can make their results available
to the community, in citable form, before we publish the edited
article. We will replace this Accepted Manuscript with the edited
and formatted Advance Article as soon as it is available.
You can find more information about Accepted Manuscripts in the
author guidelines.
Please note that technical editing may introduce minor changes
to the text and/or graphics, which may alter content. The journal’s
standard Terms & Conditions and the ethical guidelines, outlined
in our author and reviewer resource centre, still apply. In no
event shall the Royal Society of Chemistry be held responsible
for any errors or omissions in this Accepted Manuscript or any
consequences arising from the use of any information it contains.
ISSN 1477-0520
COMMUNICATION
Takeharu Haino et al.
Solvent-induced emission of organogels based on tris(phenylisoxazolyl)
benzene
rsc.li/obc

Page 1 of 6
Organic & Biomolecular Chemistry
View Article Online
DOI: 10.1039/C7OB02836A
Journal Name
ARTICLE
The Thiolation of Pentafluorobenzene with Disulfides by C–H, C–F
Bonds Activation and C-S Bond Formation
Zijian Liu,a Kunbing Ouyang*a and Nianfa Yang*a
Received 00th January 20xx,
Accepted 00th January 20xx
A metal-free thiolation reaction between pentafluorobenzene and disulfides through C–H, C–F bond activation and C-S bond
formation is reported. Bisthiolated tetrafluorobenzene derivatives would be prepared in moderate to good yield from
pentafluorobenzene and disulfides under mild condition. A possible mechanism for the reaction was given.
DOI: 10.1039/x0xx00000x
www.rsc.org/
bisarylthiolation derivatives along with tetrafluoroaryloxthines
under a similar reation condition (Scheme 1, Reaction c).9 In
2016, Hoover and co-workers10 reported the synthesis of
dithiolated compounds from pentafluorobenzoic acid and
thiophenol catalyzed by CuI in the presence of O2 (Scheme 1,
Reaction d).
Introduction
Hetero atoms such as fluorine or sulfur possess some crucial
differences from carbon and hydrogen (e.g. covalent radius and
electronegativity). Thus, the chemical and physicochemical
properties of an organic compound may be changed
dramatically by introduction of hetero atoms or heteroatom
containing groups.1 Fluorinated organic compounds could
enhance lipophilicity, metabolic stability and membrane
permeability,1f, 2 which made fluorine containing drug have a
wide range of applications3. Sulfur-containing compounds
usually have specific physiological activities,1d-f which made
them useful in pharmaceuticals and agrochemicals.4 For
compounds containing both fluorine and sulfur atoms, their
potential properties are equally attractive. For example, the
introduction of fluorine into polysulfide imide can improve the
solubility and optical transparency of polymers, which can be
widely applied in optical waveguide materials.5
a
Reaction
F
SAr
F
F
mol%)
)4 (2
RhH(PPh3
mol%)
3 (1
ArS
ArS
SAr
SAr
ArS
ArS
SAr
SAr
F
F
F
ArS
F
F
dppBz (4
PPh
eq.)
+
+
+
(ArS)2
C6H5Cl, 80
℃
F
SAr
F
SAr
5%
F
F
=
Ar p-MeC6H4
0%
95%
Reaction b
mol%)
1) RhH(PPh3)4 (1
F
mol%)
eq.)
dppe (2
S
F
F
S
PPh
THF, refl., 2 h
O
RC
3 (0.5
R'
+
F
(R'S)2
R'
C
6F
eq.)
2)
6 (2
RhH(PPh3
mol%)
mol%)
)
4 (2.5
F
dppe (5
C6
H
5Cl, refl., 3 h
c
Reaction
S
F
F
F
F
F
F
CuBr,
Synthesis of fluorinated thioether derivatives have been
reported by some groups. In 2008, Yamaguchi and co-workers6
reported the synthesis of multiple thioether compounds from
hexafluorobenzene and disulfides catalyzed by RhH(PPh3)4 and
1,2-bis(diphenylphosphino)benzene (dppBz) (Scheme 1,
Reaction a). Thioesters, which was synthesized by acid fluorides
and disulfides, could also be applied in the preparation of
thioether compounds (Scheme 1, Reaction b).7 In 2012, Shi and
H
2O
F
F
H
phen
ArS
F
F
ArS
F
F
H
F
t-BuOLi
Ar
+
+
+
Ar
S
DDQ
DMSO
F
F
SAr
F
F
SAr
F
60
O
2
℃
,
F
F
F
F
ArS
F
F
F
F
S
F
H
CuBr, t-BuOLi
DMSO
SH
+
+
R
Ar
L
100
O
,
SAr
O
F
F
O
2
℃
,
N
F
F
OH
L
Reaction d
co-workers8 developed
a CuBr catalyzed synthesis of
bisarylthiolation derivatives from pentafluorobenzene and
diaryl disulfides in the presence of O2. They also found that aryl
thiols could be used instead of diaryl disulfides to yield
F
O
F
F
CuI
mol%)
(10
F
F
HS
mol%)
phen (12
S
F
OH
K
2CO
eq.)
3 (1.0
+
DMF, 140
24 h
℃
,
F
S
4A MS, O2 balloon
,
F
F
Scheme 1 Synthetic methods for diaryl thioether compounds
a.Key Laboratory for Green Organic Synthesis and Application of Hunan
Province,Key Laboratory of Environmentally Friendly Chemistry and Application of
Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan
411105, China. E-mail: kbouyang@xtu.edu.cn; nfyang@xtu.edu.cn ; Fax: +86-731-
58292251; Tel: +86-731-58292251.
The synthetic methods mentioned above share some
drawbacks which limits further applications of these reactions:
Electronic Supplementary Information (ESI) available: [details of any supplementary 1) employment of expensive transition metal catalysts; 2)
information available should be included here]. See DOI: 10.1039/x0xx00000x
This journal is © The Royal Society of Chemistry 2017
Org. Biomol. Chem.

Please do not adjust margins
Organic & Biomolecular Chemistry
Page 2 of 6
ARTICLE
Journal Name
employment of excess of malodorous thiols or thiophenol; 3) target product 3a (Table 1, entry 6). Various basVeieswsAurtcichle Oanslinte-
relatively high reaction temperature; 3) generation of BuOLi, t-BuONa, t-BuOK, LiOH, NaOH, DKOOI:H1,0.1C0a3(9O/CH7)O2,B0N2(8E3t6)A3
byproducts.6-10 This paper developed an environment-friendly were investigated.The addition of KOH gave the highest yield of
and effective synthetic method for the preparation of 3a (Table 1, entries 7 ~ 13). Later, different solvents were
fluorinated sulphides under mild condition.
screened and DMF performed best (Table 1, entries 14 ~ 17). In
general, DMF has a better solubility for inorganic substances
than other solvents, indicating that solvent solubility of
inorganic bases has a significant effect in this reaction. In
summary, the optimal reaction conditions for the thiolation of
pentafluorobenzene with disulfides were released: the ratio of
disulfides, pentafluorobenzene and KOH was 2 : 1 : 2, DMF as
Results and discussion
Initially, attempts on the reaction of pentafluorobenzene (2,
0.5 mmol) and dimethyl disulfide (1a, 0.5 mmol) in the presence
of t-BuOK (1 mmol) gave 1,4-bis(methylmercapto)-tetrafluoro-
benzene (3a) (Scheme 2).
solvent, 25℃, 10 h.
F
F
F
F
H
F
S
F
F
S
mmol
1
t-BuOK
S
+
S
DMF
25 , 10 h
Table 2 Scope of thiolation for disulfides and pentafluorobenzene. a, b
℃
F
F
F
F
F
H
S
F
mmol
mmol
1a
2
0.5
,
0.5
,
mmol
3a 0.25
,
KOH
DMF
R
S
R
+
R
S
R
F
F
F
S
25
10 h
,
℃
F
F
Scheme 2 The reaction of pentafluorobenzene and dimethyl disulfide
Table 1 Optimization of the reaction condition. a
1a~q
2
3a~q
F
F
F
F
F
S
F
S
F
F
S
S
F
F
S
F
F
F
F
H
S
base
F
S
S
+
S
F
solvent
F
S
F
F
25
10 h
℃
,
3b
F
F
3a
(90%)
F
3c
(97%)
F
(95%)
F
1a
2
3a
O
F
S
S
S
F
F
S
S
F
Entry
1
1a
:
2
Base (equiv.)b
t-BuOK (2.0)
t-BuOK (2.0)d
t-BuOK (2.0)
t-BuOK (0.5)
t-BuOK (1.0)
t-BuOK (3.0)
t-BuOLi (2.0)
t-BuONa (2.0)
LiOH (2.0)
Solvent
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
THF
Yield (%)c
50
35d
F
F
S
1 : 1
1 : 2
2 : 1
2 : 1
2 : 1
2 : 1
2 : 1
2 : 1
2 : 1
2 : 1
2 : 1
2 : 1
2 : 1
2 : 1
2 : 1
2 : 1
2 : 1
F
F
O
F
2
3d
3e
3f
(54%)
F
(44%)
(46%)
F
3
57
F
S
F
F
S
F
F
S
S
F
F
OMe
4
20
5
38
S
MeO
S
F
F
F
6
18
3g
3h
3i
(80%)
(63%)
(89%)
7
63
F
F
F
F
F
8
40
F
S
S
F
F
S
NH2
O2
N
F
9
Trace
73
O2
N
F
H2
N
S
F
F
10
11
12
13
14
15
16
17
NaOH (2.0)
KOH (2.0)
c
3j
3l
3k
(70%)
F
(trace)
F
(12%)
97
F
F
Ca(OH)2 (2.0)
NEt3 (2.0)
n.d.e
n.d.e
Trace
14
S
F
S
Cl
S
F
F
S
S
F
N
N
Cl
F
F
S
KOH (2.0)
F
F
F
F
3m
(65%)
3n
3o
(73%)
KOH (2.0)
DME
MeCN
CH2Cl2
(62%)
KOH (2.0)
20
n.d.e
F
F
S
F
F
S
F
S
S
F
S
KOH (2.0)
O
S
O
a
b
c
All reaction temperature was 25
was based on
standard substance. d Equivalent was based on 1a
℃
.
Equivalent was based on
2
.
Yield
F
F
2
and determined by GC, using dodecane as an internal
e n.d. = no detection.
3p
(62%)
3q
(71%)
.
a Reaction conditions:
1 (0.8 mmol, 2 equiv.), 2 (0.4 mmol, 1 equiv.), KOH (0.8
mmol, 2 equiv.), DMF (2 mL). b Isolated yield. c NMR yield determined by 19
NMR, using benzotrifluoride as an internal standard substance.
F
This reaction was chosen as the model reaction and different
conditions were screened. These results are shown in Table 1.
Initially, different ratio of 1a and
presence of excess t-BuOK. The desired product 3a could be
obtained in relatively high yield while the ratio of 1a to was 2
: 1 (Table 1, entries 1 ~ 3). Then different amount of base was
investigated. Based on the amount of , it was found that 2
equivalent of t-BuOK gave the highest yield of 3a (Table 1,
entries 3 ~ 6). Employment of excess base led to the formation
of multi-substituted products, thus reducing the yield of the
2 was investigated in the
With the above optimal conditions in hand, we explored
scope of this reaction (Table 2). As given in Table 2, most linear
2
alkyl disulfides could react with
excellent yields of the corresponding products (Table 2, 3a
2
smoothly to give high to
3c
-
,
2
yield: 90%~97%). However, the yield of bis(butylthio)-2,3,5,6-
tetrafluorobenzene (3d) decreased obviously compare to that
of 3a
~
3c when dibutyl disulphide (1d) was used in this reaction.
2 | J. Name., 2017, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins

Page 3 of 6
Organic & Biomolecular Chemistry
Please do not adjust margins
Journal Name
ARTICLE
Benzyl disulfide (1e) and dithenyl disufide (1f) could also be
employed in this reaction to give corresponding products 1,4-
bis(benzylthio)-2,3,5,6-tetrafluorobenzene (3e, 44% yield) and
1,4-bis(furfurylthio)-2,3,5,6-tetrafluorobenzene (3f, 46% yield).
In the series reactions of diaryl disulfides, diphenyl disulfide (1g
Entry
1
R
R1
Product (yield) b
View Article Online
F
DOI: 10.1039/C7OB02836A
F
S
H
CH3
S
F
F
5b
(40%)
F
F
S
S
F
) could react with
corresponding product 3g in 63% yield. Aryl disulfides
substituted with electron-donating groups gave corresponding
products in relatively high yields (Table 2, 3h
employment of aryl disulfides substituted with electron-
withdrawing groups gave corresponding products in moderate
2 under optimal conditions to give
2
3
4
H
H
H
n-Pr
F
5c
(34%)
~ 3j ). However,
F
F
S
S
p-CH3C6H4
2-pyridyl
F
F
to good yields. (Table 2, 3m
nitrophenyl) disulfide (1k) and bis(3-nitrophenyl) disulfide (1l
reacted with only gave (4-nitrophenyl)(2,3,5,6-
tetrafluorophenyl)sulfane 3k and (3-nitrophenyl)(2,3,5,6-
tetrafluorophenyl)-sulfane (3l) in low yields. Heterocyclic
substituted products (3o 3p and 3q) could be prepared in
, 3n ). In particularly, bis(4-
5d
(56%)
F
)
F
S
S
F
N
2
(
)
F
5e
(57%)
F
,
F
S
F
moderate yields from disulfides 2,2'-dipyridyl disulfide (1o),
2,2'-dithienyl disulfide (1p) and bis(2-methyl-3-furyl)disulphide
5
6
7
8
CH3
CH3
CH3
CH3
CH3
n-Pr
C6H5
S
F
5f
(39%)
F
(1q) via this reaction.
F
S
S
Table 3 The reaction of asymmetric disulfides and pentafluorobenzene. a, b
F
R2
F
S
S
R1
5g (32%)
F
F
F
4
+
F
F
S
S
F
F
S
S
F
KOH
DMF
F
S
S
F
R1
R2
R2
F
S
S
+
+
F
R1
R2
R1
25 , 10 h
℃
H
F
F
F
F
F
F
F
5
F
3'
3''
5d
F
(52%)
F
F
2
S
F
N
Total
R1
CH3
R2
n-Pr
3’
5
3’’
2-pyridyl
Entry
S
yields
F
5h
(51%)
10%
38%
31%
3c
43%
3l
36%
3f
1
2
3
79%
43%
57%
a Reaction conditions:
mmol, 1 equiv.), DMF (2 mL). b Isolated yield.
7
(0.4 mmol, 1 equiv.),
1
(0.4 mmol, 1 equiv.), KOH (0.4
(
3a
)
(
5a
)
(
)
2-pyridyl
CH3
p-ClC6H4
-
-
(
)
21%
F
S
furfuryl
-
SNa
H
F
F
F
(
3a
)
(
)
DMF, 25
℃
F
S
H
F
+
a Reaction conditions:
4
(0.8 mmol, 2 equiv.),
2
(0.4 mmol, 1 equiv.), KOH (0.8
F
S
mmol, 2 equiv.), DMF (2 mL). b NMR yields determined by 19F NMR, using
mmol)
mmol)
4
2
(0.4
(2.4
benzotrifluoride as an internal standard substance.
8
(74%)
Scheme 4 The reaction of sodium thiophenolate and pentafluorobenzene.
F
S
R2
R1
S
or
R2
S
F
S
S
F
F
R1
F
B
R1
R
F
S
H
F
a
SN
,
H
F
F
F
DMF 25
℃
F
F
+
R1
F
S
R1
S
F
F
H
F
F
S
H
F
C
R
Base
F
or
F
F
Base
R1
F
F
2
6
7
F
S
S
F
,
R1
S
=
=
R
R
H
65
R2
2
A
%
%
,
R1
CH3 40
B
Scheme 3 The reaction of arylthiols sodium and pentafluorobenzene.
F
D
Scheme 5 Plausible mechanism.
Table 4 The reaction of arylsulfane tetrafluorobenzene and disulfides. a
F
F
F
F
R
F
S
H
F
R
F
S
S
F
R1
KOH
+
R1
S
R1
S
Reactions of asymmetric disulfides (
conducted (Table 3). Methyl propyl disulphide (4a) could react
4
) and
2
were also
DMF, 25
10 h
℃
7
1
5
with
2
to generate 3a (10%), 3c (31%) and methyl(2,3,5,6-
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2017, 00, 1-3 | 3
Please do not adjust margins

Please do not adjust margins
Organic & Biomolecular Chemistry
Page 4 of 6
ARTICLE
Journal Name
There are no conflicts to declare.
tetrafluoro-4-propylthiophenyl)sulfane (5a, 38%). When 2-((4-
chlorophenyl)disulfanyl)pyridine 4b was applied in this
reaction, only 3l was received in 43% yield. Methyl 2-methyl-3-
furyl disulphide (4c) could react with under the optimal
View Article Online
DOI: 10.1039/C7OB02836A
(
)
Acknowledgements
2
conditions, generating 3a in 21% yield and 3f in 36% yield.
Several experiments were conducted to investigate the
mechanism of this process. 1). A DMF solution of sodium
We are grateful to the National Science Foundation of China
(21602188), the Education Department of Hunan Province
(17C1524) and Xiangtan University (15QDZ52) for financial
support of this work.
thiophenolate (6a) or 4-methylbenzenethiol sodium (6b) and
2
(1 : 1) were stirred overnight, generating 1-phenylthio-2,3,5,6-
tetrafluorobenzene (7a, 65% yield) or 2,3,5,6-tetrafluoro-1-(p-
tolylthio)benzene (7b, 40% yield) as the major product (Scheme
Notes and references
3); 2).
condition, giving corresponding products
(Table 4). As shown in Table 4, 7a could react with series of
1a 1c 1h and 1o) to yield 5b (40%), 5c (34%), 5d (56%) and 5e
7
could react with various disulfides under the optimal
1. (a) B. M. Trost, Chem. Rev., 1978, 78, 363-382; (b) M. D.
McReynolds, J. M. Dougherty and P. R. Hanson, Chem. Rev.,
2004, 104, 2239-2258; (c) M. Matsugi, K. Murata, H. Nambu
and Y. Kita, Tetrahedron Lett., 2001, 42, 1077-1080; (d) C. J.
Yu, Y. Chong, J. F. Kayyem and M. Gozin, J. Org. Chem., 1999,
64, 2070-2079; (e) K. Müller, C. Faeh and F. Diederich,
Science, 2007, 317, 1881-1886; (f) S. Purser, P. R. Moore, S.
Swallow and V. Gouverneur, Chem. Soc. Rev., 2008, 37, 320-
330.
2. (a) M. Müller, C. M. Orben, N. Schützenmeister, M. Schmidt,
A. Leonov, U. M. Reinscheid, B. Dittrich and C. Griesinger,
Angew. Chem. Int. Ed., 2013, 52, 6047-6049; (b) J. Wang, M.
Sánchez-Roselló, J. L. Aceña, C. del Pozo, A. E. Sorochinsky, S.
5
in moderate yields
1
(
,
,
(57%) in the presence of KOH (Table 4, entries 1 ~ 4). Similarly,
5f (39%), 5g (32%), 5d (52%) and 5h (51%) could be prepared
from 7b and corresponding disulfides (1a
the optimal conditions; 3). Employment of excess
gave product 1,2,4-tris(phenylthio)-3,6-difluorobenzene (
74% yield (Scheme 4); 4). As mentioned above, the reaction of
1k 1l and only gave 3k and 3l in low yields. These results
indicated that sulfhydryl anion could substitute the fluorine
atom at the C-4 position of , and the hydrogen of could be
extracted by KOH. However, the shedding of fluorine at the C-4
position of was also easier than that hydrogen.
Based on the above preliminary results,
,
1c
,
1g and 1o) under
with only
) in
4
2
8
,
2
Fustero, V. A. Soloshonok and H. Liu, Chem. Rev., 2014, 114
2432-2506.
,
2
2
3. (a) J.-P. Bégué and D. Bonnet-Delpon, J. Fluorine Chem.,
2006, 127, 992-1012; (b) C. Isanbor and D. O’Hagan, J.
Fluorine Chem., 2006, 127, 303-319; (c) D. Karl and M.
2
a
plausible
Muhammad, Curr. Top. Med. Chem., 2003, 3, 249-282; (d)
mechanism was proposed in Scheme 4. As reported by Kisliuk,
Taddei and other people, base could help activating the
disulfide via homolytic cleavage.11 Initially, reactive sulfhydryl
ion intermediates were generated from disulfides in the
presence of base. The reactive sulfhydryl ion then reacted with
K. L. Kirk, J. Fluorine Chem., 2006, 127, 1013-1029; (e) R.
Laszlo, K. A. Menzel, K. Bentz, B. Schreiner, K. Kettering, C.
Eick and J. Schreieck, Life Sci., 2010, 87, 507-513; (f) D. T.
Wong, F. P. Bymaster and E. A. Engleman, Life Sci., 1995,
57, 411-441.
the C-F bond at C-4 position of
2 to provide intermediate A.
4. (a) E. Sauvage, F. Kerff, M. Terrak, J. A. Ayala and P. Charlier,
FEMS Microbiol. Rev., 2008, 32, 234-258. (b) M. Tomizawa
and J. E. Casida, Annu. Rev. Entomol., 2003, 48, 339-364; (c)
P. Jeschke, R. Nauen, M. Schindler and A. Elbert, J. Agric.
Food. Chem., 2011, 59, 2897-2908.
5. C.-P. Yang, Y.-Y. Su and M.-Y. Hsu, Polym. J, 2006, 38, 132-
144.
6. M. Arisawa, T. Suzuki, T. Ishikawa and M. Yamaguchi, J. Am.
Chem. Soc., 2008, 130, 12214-12215.
7. M. Arisawa, T. Yamada and M. Yamaguchi, Tetrahedron
Lett., 2010, 51, 6090-6092.
Then the C-H bond would be broken in the presence of base,
followed by reaction with reactive sulfhydryl ion intermediates
B
or other disulfides to give corresponding products C or D.
However, employment of excess base would destroy more
disulfides at the beginning of the reaction, thus leading to the
break of more C-F bonds of pentafluorobenzene in the first step
and the formation of multi-substituted products. This would
limit the second step, resulting in a decrease in the yield of
desired products.
8. C. Yu, C. Zhang and X. Shi, Eur. J. Org. Chem., 2012, 2012
,
1953-1959.
Conclusions
9. C. Yu, G. Hu, C. Zhang, R. Wu, H. Ye, G. Yang and X. Shi, J.
Fluorine Chem., 2013, 153, 33-38.
10. M. Li and J. M. Hoover, Chem Commun (Camb), 2016, 52
In conclusion, the thiolation of pentafluorobenzene with
disulfides by C–H, C–F bonds activation and C-S bond formation
was demonstrated. This is a new and environment-friendly
methodology of thiolation reaction. The reaction proceeds
under mild and metal-free conditions, and the corresponding
products were obtained in moderate to good yields. A possible
mechanism for the reaction was given through some
experiments.
,
8733-8736.
11. (a) A. Gangjee, R. Devraj, J. J. McGuire and R. L. Kisliuk, J.
Med. Chem., 1995, 38, 4495-4502; (b) S. Antonello, R.
Benassi, G. Gavioli, F. Taddei and F. Maran, J. Am. Chem.
Soc., 2002, 124, 7529-7538; (c) C. M. Wright, P. M.
Palenchar and E. G. Mueller, Chem. Commun., 2002, DOI:
10.1039/B208626C, 2708-2709; (d) N. Taniguchi, The
Journal of Organic Chemistry, 2006, 71, 7874-7876; (e) Q.
Zhou, B. Zhang, H. Gu, A. Zhong, T. Du, Q Zhou, Y. Ye, Z. Jin,
Conflicts of interest
H. Jiang and R. Chen, Lett. Org. Chem. 2012, 9, 175-181. (f)
K. Moriya, D. Didier, M. Simon, J. M. Hammann, G. Berionni,
4 | J. Name., 2017, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins

Page 5 of 6
Organic & Biomolecular Chemistry
Please do not adjust margins
Journal Name
ARTICLE
K. Karaghiosoff, H. Zipse, H. Mayr and P. Knochel, Angew.
Chem. Int. Ed., 2015, 54, 2754-2757.
View Article Online
DOI: 10.1039/C7OB02836A
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2017, 00, 1-3 | 5
Please do not adjust margins

Organic & Biomolecular Chemistry
Page 6 of 6
View Article Online
DOI: 10.1039/C7OB02836A
103x31mm (300 x 300 DPI)