Photoinduced synthesis of 2-sulfonylacetonitriles with the insertion of sulfur dioxide under ultraviolet irradiation

Article abstract of DOI:10.1039/d0cc00351d

Metal-free insertion of sulfur dioxide with aryl iodides and 3-azido-2-methylbut-3-en-2-ol under ultraviolet irradiation at room temperature is achieved, giving rise to 2-(arylsulfonyl)acetonitriles in moderate to good yields. Alkyl iodide is also workable under these conditions. This transformation proceeds smoothly under mild conditions with a broad substrate scope. Various functional groups are compatible including amino, ester, halo, and trifluoromethyl groups. No metal catalyst or additive is needed during the reaction process. Mechanistic studies show that under ultraviolet irradiation, an aryl radical is generated in situ from aryl iodide, which undergoes subsequent sulfonylation via the insertion of sulfur dioxide leading to arylsulfonyl radical intermediates. Then the arylsulfonyl radical reacts with 3-azido-2-methylbut-3-en-2-ol giving rise to the corresponding 2-(arylsulfonyl)acetonitrile.

Full text of DOI:10.1039/d0cc00351d

View Article Online
View Journal
ChemComm
Chemical Communications
Accepted Manuscript
This article can be cited before page numbers have been issued, to do this please use: K. Zhou, J. Liu, W.
Xie, S. Ye and J. Wu, Chem. Commun., 2020, DOI: 10.1039/D0CC00351D.
Volume 54
This is an Accepted Manuscript, which has been through the
Number
January 2018
Pages 1-112
1
4
Royal Society of Chemistry peer review process and has been
accepted for publication.
ChemComm
Chemical Communications
rsc.li/chemcomm
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
Information for Authors.
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 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 1359-7345
COMMUNICATION
S. J. Connon, M. O. Senge et al.
Conformational control of nonplanar free base porphyrins:
towards bifunctional catalysts of tunable basicity
rsc.li/chemcomm

Page 1 of 4
ChemComm
View Article Online
DOI: 10.1039/D0CC00351D
ChemComm
COMMUNICATION
Photoinduced synthesis of 2-sulfonylacetonitriles with the
insertion of sulfur dioxide under ultraviolet irradiation
Kaida Zhou,a Jin-Biao Liu,b Wenlin Xie,c Shengqing Ye,*a and Jie Wu*a,d
Received 00th January 20xx,
Accepted 00th January 20xx
Metal-free insertion of sulfur dioxide with aryl iodides and 3-azido-2-methylbut-3-en-2-ol under ultraviolet irradiation at
room temperature is achieved, giving rise to 2-(arylsulfonyl)acetonitriles in moderate to good yields. Alkyl iodide is also
workable under the conditions. This transformation proceeds smoothly under mild conditions with broad substrate scope.
Various functional groups are compatible including amino, ester, halo, and trifluoromethyl groups. No metal catalyst or
additive is needed during the reaction process. Mechanistic studies show that under ultraviolet irradiation, aryl radical is
generated in situ from aryl iodide, which undergoes subsequent sulfonylation via insertion of sulfur dioxide leading to
arylsulfonyl radical intermediate. Then arylsulfonyl radical reacts with 3-azido-2-methylbut-3-en-2-ol giving rise to the
corresponding 2-(arylsulfonyl)acetonitrile.
DOI: 10.1039/x0xx00000x
www.rsc.org/
In the past few years, focus on the preparation of sulfonyl Triazolothienopyrimidine UT-B inhibitors synthesized from 2-
compounds has been centred on the insertion of sulfur dioxide by (arylsulfonyl)acetonitriles can selectively and reversibly inhibit urea
using the sulfur dioxide surrogates of DABCO·(SO2)2 (1,4- transport and reduced urinary concentration in mice.11 Additionally,
diazabicyclo[2.2.2]octane-sulfur dioxide)1,2 or potassium/sodium arylsulfonylacetonitriles can be used to synthesize β-aminonitriles
metabisulfite.3 Many approaches have been appeared in the and β-keto sulfones, which are used to synthesize pesticides, food,
presence of metal catalysis or under photoinduced conditions.4 Due medicine and feed additives.12 Therefore, continuous efforts have
to the importance of sulfonyl-containing drugs and related been given for the generation of arylsulfonylacetonitriles. Traditional
compounds,5 we are also involved in this area and have developed synthesis of arylsulfonylacetonitriles includes the use of toxic
several strategies with the insertion of sulfur dioxide via radical sulfonyl chlorides,13 sulfonic acids or salts,14 haloacetonitriles,15 or
process.6 For instance, we reported an example by using Katritzky harsh reaction conditions that require additional catalysts, oxidants
salts as alkyl radical precursors with the insertion of sulfur dioxide and additional reaction steps.16
under photoredox catalysis, leading to diverse dialkyl sulfones.6g
N3
O
O
Recently, the photoinduced reactions of aryl iodides under visible
light or ultraviolet irradiation have been developed rapidly.7,8 It is
noteworthy that the cleavage of C-I bond can occur under catalyst-
free conditions via ultraviolet irradiation, with the generation of aryl
radical intermediate. For example, arylboronic acids could be
prepared through a catalyst- and additive-free, photoinduced
borylation of haloarenes under ultraviolet irradiation.9a
h
N
Ar
I
+
DABCO (SO2)2
+
S
C
OH
Ar
2
1
3
Ar
I
h
O
O
1
S
CN
Ar
Ar
3
OH
I
SO2
C
O
2-(Arylsulfonyl)acetonitriles have a wide range of biological
activities and are broadly used in the synthesis of pharmaceuticals
natural products intermediates. For example, sulfanylacrylonitril
derivatives are inhibitors of the diadenosine tetraphosphate
phosphorylase Rv2613c of mycobacterium tuberculosis.10
- HI
N
O
O
O
O
S
OH
S
Ar
Ar
B
N3
- N2
N3
OH
O
O
S
OH
2
Ar
a. School of Pharmaceutical and Materials Engineering & Institute for Advanced Studies,
Taizhou University, 1139 Shifu Avenue, Taizhou 318000, China. Email:
ysq0607@gmail.com; jie_wu@fudan.edu.cn
A
Scheme 1. A proposed route to 2-(arylsulfonyl)acetonitriles through the
insertion of sulfur dioxide under photoinduced metal-free conditions
b. School of Metallurgical and Chemical Engineering, Jiangxi University of Science
and Technology, Ganzhou 341000, China
c. School of Chemistry and Chemical Engineering, Hunan University of Science and
Technology, Xiangtan 411201, China
Prompted by the recent advance of photoinduced reactions
of aryl halides under ultraviolet irradiation and the results of
sulfur dioxide chemistry, we envisioned that the photoinduced
insertion of sulfur dioxide into aryl iodides might be feasible for
d. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic
Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032,
China
Electronic Supplementary Information (ESI) available: [details of any supplementary
information available should be included here]. See DOI: 10.1039/x0xx00000x
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 1
Please do not adjust margins

ChemComm
Page 2 of 4
Communication
ChemComm
the preparation of arylsulfonylacetonitriles under ultraviolet yield was inferior when DCE or MeOH was used as the solvent
View Article Online
DOI: 10.1039/D0CC00351D
to (Table 1, entries 4 and 5). The result was slightly lower when the
irradiation.
A
proposed
synthetic
route
arylsulfonylacetonitriles is shown in Scheme 1. 3-Azido-2- sulfur dioxide surrogate of DABCO·(SO2)2 was changed to
methylbut-3-en-2-ol was used as the reaction partner, with an potassium metabisulfite (Table 1, entry 6). However, the
expectation to introduce cyano group in the molecule of reaction was hampered when sodium metabisulfite was used
arylsulfonylacetonitrile. We conceived that under ultraviolet instead (Table 1, entry 7). Interestingly, the yield was increased
irradiation, aryl radical would be generated from aryl iodide 1 in to 52% when 3.0 equiv of potassium metabisulfite was
the absence of metal- and additive-free conditions. employed (Table 1, entry 8). The result could be further
Subsequently, aryl radical would react with DABCO·(SO2)2 to improved by using 3.0 equiv of DABCO·(SO2)2 (Table 1, entry 9).
provide arylsulfonyl radical, with the release of DABCO. Then The ratio of reaction partners was subsequently evaluated. A
arylsulfonyl radical would attack the double bond of 3-azido-2- higher yield was afforded when 2.0 equiv of 1-iodo-4-
methylbut-3-en-2-ol 2, leading to radical intermediate A. A methylbenzene 1a was utilized (Table 1, entry 10). The
molecule of nitrogen would be released form intermediate A corresponding 2-tosylacetonitrile 3a was produced in 73% yield
giving rise to nitrogen radical intermediate B, which would when the reaction time was extended to 24 h (Table 1, entry 11).
undergo C-C bond cleavage to produce arylsulfonylacetonitrile No better yield was observed when the amount of substrate 1a
3. Meanwhile, radical C would be generated, which would was increased (Table 1, entry 12).
combine with iodo radical. Finally, deprotonation by DABCO
would afford acetone as byproduct.
Table 2. Scope exploration for the photoinduced synthesis of 2-
(arylsulfonyl)acetonitriles with the insertion of sulfur dioxide under
Table 1. Initial studies for the photoinduced synthesis of 2- ultraviolet irradiation a
(arylsulfonyl)acetonitrile with the insertion of sulfur dioxide under
ultraviolet irradiation a
O
O
N3
OH
2
I
N
UV (600 W)
N2, rt
S
C
R
+
DABCO (SO2)2 +
R
N3
I
3
1
UV (600 W)
N2, rt
O
O
N
+
SO2
+
S
C
OH
p-Tol
O
O
O
O
O
O
O
O
S
CN
S
CN
MeO
S
CN
Br
S
CN
CN
1a
Entry
2
3a
Solvent
MeCN
“SO2“
Time Yield (%)b
3a
3b
3c
3d
, 51%
, 73%
, 55%
, 61%
1
2
DABCO·(SO2)2
DABCO·(SO2)2
DABCO·(SO2)2
DABCO·(SO2)2
DABCO·(SO2)2
K2S2O5
12 h
12 h
12 h
12 h
12 h
12 h
12 h
12 h
30
trace
trace
6
O
O
O
O
O
O
O
O
S
CN
S
CN
F3C
S
CN
Ph
S
1,4-dioxane
THF
3
F
Cl
4
DCE
3e
3f
3g
3h
, 40%
, 61%
, 51%
, 76%
O
5
MeOH
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
20
O
O
O
O
O
O
O
S
CN
S
CN
S
CN
S
CN
6
26
7
Na2S2O5
trace
52
COOMe
3i
3j
3k
3l
, 77%
, 41%
, 48%
, 53%
8
K2S2O5 (3.0 equiv)
9
DABCO·(SO2)2 (3.0 equiv) 12 h
DABCO·(SO2)2 (3.0 equiv) 12 h
DABCO·(SO2)2 (3.0 equiv) 24 h
DABCO·(SO2)2 (3.0 equiv) 24 h
59
O
S
O
O
O
O
O
S
O
O
CN
S
CN
tBu
CN
S
CN
CN
CN
10c
11c
12d
62
H2N
I
73
3m
3n
3o
3p
, 52%
, 80%
CN
, 53%
, 55%
CN
55
O
O
O
O
O
O
O
O
a
Reaction conditions: 1-iodo-4-methylbenzene 1a (0.3 mmol),
S
S
I
CN
S
MeO
S
DABCO.(SO2)2 (0.2 mmol), 3-azido-2-methylbut-3-en-2-ol 2 (0.2 mmol),
solvent (4.0 mL), N2. b Isolated yield based on 3-azido-2-methylbut-3-en-
2-ol 2. c In the presence of 1-iodo-4-methylbenzene 1a (0.4 mmol). d In
the presence of 1-iodo-4-methylbenzene 1a (0.5 mmol).
S
Cl
3q
3s
3t
, 67%
3r
, 50%
, 88%
, 36%
O
S
O
O
O
O
O
O
O
CN
S
CN
S
CN
S
F
NH2
, 52%
CF3
Br
With the above consideration in mind, we thus started to
explore the practicability of the hypothesis in Scheme 1. Initially,
the reaction of 1-iodo-4-methylbenzene 1a, DABCO·(SO2)2, and
3-azido-2-methylbut-3-en-2-ol 2 was selected for method
development. At the outset, the reaction was performed in
MeCN at room temperature under ultraviolet irradiation (600
W, Table 1, entry 1). To our delight, the desired 2-
tosylacetonitrile product 3a was obtained in 30% yield. Only a
trace amount of product was detected when the reaction
occurred in THF or 1,4-dioxane (Table 1, entries 2 and 3). The
3v
3w
3x
3u
, 50%
, 43%
, 61%
O
O
S
CN
NH2
, 53%
3y
a Isolated yield based on aryl iodide 1.
2 | J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx

Page 3 of 4
ChemComm
Please do not adjust margins
ChemComm
Communication
We next explored the scope generality of this method under would take place to produce arylsulfonylacetonitrile and
View Article Online
the optimized conditions, and the result is shown in Table 2. A acetone. Thus, we examined the reaction of
DOI: 10.1039/D0C-Cio00d3o5-14D-
range of aryl iodides was examined, and it was found that all methylbenzene 1a, DABCO·(SO2)2, and 2-azido-1,1-
reactions proceeded smoothly giving rise to the desired diphenylprop-2-en-1-ol 5. Consequently, the desired product 3a
products in moderate to good yields under ultraviolet was observed and isolated in 57% yield, with the release of
irradiation. Additionally, this three-component reaction of aryl benzophenone. All these results demonstrated that the
iodides 1, DABCO·(SO2)2, and 3-azido-2-methylbut-3-en-2-ol 2 proposed route in Scheme 1 was reasonable.
showed good functional group tolerance, and many sensitive
In conclusion, we have reported a catalyst- and additive-free
groups were compatible under the standard conditions. For process for the synthesis of 2-(arylsulfonyl)acetonitriles from
example, the amino-substituted product 3m was afforded in 80 aryl iodides, 3-azido-2-methylbut-3-en-2-ol, and sulfur dioxide
yield, and the ester-containing product 3l was produced in 77% under ultraviolet irradiation at room temperature. This
yield. The ortho-substituted aryl iodides were workable as well, transformation proceeds smoothly under mild conditions with
although the results were not as good as expected. For instance, broad
substrate
scope,
giving
rise
to
2-
ortho-trifluoromethyl substituted product 3u was generated in (arylsulfonyl)acetonitriles in moderate to good yields. Various
61% yield, while 2-((2-(methylthio)phenyl)sulfonyl)acetonitrile functional groups including amino, ester, halo, and
3q was provided in 67% yield. Additionally, the reaction was trifluoromethyl groups are compatible under the conditions.
only effective for aryl iodides. Aryl bromides, chlorides and Alkyl iodide is also workable under the conditions. Mechanistic
fluorides were inert under the conditions.
studies show that under ultraviolet irradiation, aryl radical is
generated in situ from aryl iodide, which undergoes subsequent
sulfonylation via insertion of sulfur dioxide leading to
arylsulfonyl radical intermediate. Then arylsulfonyl radical
reacts with 3-azido-2-methylbut-3-en-2-ol giving rise to the
corresponding 2-(arylsulfonyl)acetonitrile.
O
O
N3
OH
2
I
UV (600 W)
N2, rt
S
CN
+
DABCO (SO2)2 +
3z
4
, 40%
Financial support from National Natural Science Foundation
of China (Nos. 21672037 and 21532001) is gratefully
acknowledged.
Scheme 2. Further exploration
We further explored the reaction of cyclohexyl iodide 4,
DABCO·(SO2)2 and 3-azido-2-methylbut-3-en-2-ol under
ultraviolet irradiation (600 W) at room temperature (Scheme 2).
As expected, the corresponding product 3z was produced in 40%
yield. This result also demonstrated that alkyl iodide was good
partner as well in this transformation.
2
Conflicts of interest
There are no conflicts to declare.
Notes and references
1
2
P. S. Santos and M. T. S. Mello, J. Mol. Struc., 1988, 178, 121.
For selected examples, see: (a) B. Nguyen, E. J. Emmet and M. C.
Willis, J. Am. Chem. Soc., 2010, 132, 16372; (b) Y. Chen, P. R. D.
Murray, A. T. Davies and M. C. Willis, J. Am. Chem. Soc., 2018, 140,
8781; (c) D. Zheng, Y. An, Z. Li and J. Wu, Angew. Chem. Int. Ed., 2014,
53, 2451; (d) D. Zheng, J. Yu and J. Wu, Angew. Chem. Int. Ed., 2016,
55, 11925; (e) X. Gong, M. Wang, S. Ye and J. Wu, Org. Lett., 2019, 21,
1156; (f) S. Ye, G. Qiu and J. Wu, Chem. Commun., 2019, 55, 1013; (g)
S. Ye, D. Zheng, J. Wu and G. Qiu, Chem. Commun., 2019, 55, 2214; (h)
S. Ye, Y. Li, J. Wu and Z. Li, Chem. Commun., 2019, 55, 2489; (i) X. Gong,
X. Li, W. Xie, J. Wu and S. Ye, Org. Chem. Front., 2019, 6, 1863; (j) S.
Ye, T. Xiang, X. Li and J. Wu, Org. Chem. Front., 2019, 6, 2183; (k) J.
Zhang, W. Xie, S. Ye and J. Wu, Org. Chem. Front., 2019, 6, 2254; (l) F.-
S. He, X. Gong, P. Rojsitthisak and J. Wu, J. Org. Chem., 2019, 84,
13159; (m) S. Ye, X. Li, W. Xie and J. Wu, Asian J. Org. Chem., 2019, 8,
893; (n) S. Ye, K. Zhou, P. Rojsitthisak and J. Wu, Org. Chem. Front.,
2020, 7, 14. (o) S. Ye and J. Wu, Acta Chim. Sinica, 2019, 77, 814; (p)
F.-S. He, S. Ye and J. Wu, ACS Catal., 2019, 9, 8943.
I
N3
no UV light
N2, rt
O
O
+
+
DABCO (SO2)2
+
+
S
CN
(1)
(2)
(3)
OH
p-Tol
1a
1a
1a
3a
2
, n.d.
I
N3
OH
DABCO (SO2)2
UV (600 W)
N2, rt
O
O
S
CN
p-Tol
TEMPO (2.0 equiv)
3a
2
, n.d.
I
N3
OH
UV (600 W)
N2, rt
O
O
+
DABCO (SO2)2
+
Ph
S
CN
p-Tol
Ph
3a
5
, 57%
Scheme 3. Investigation of the mechanism
3
4
S. Ye, G. Qiu and J. Wu, Chem. Commun., 2019, 55, 1013.
To get more insight for the mechanism, several control
experiments were performed (Scheme 3). It was shown that no
reaction occurred in the absence of ultraviolet irradiation
(Scheme 3, eqn 1). Since this route might be proceeded through
a radical process as hypothesized in Scheme 1, we therefore
investigated the reaction of 1-iodo-4-methylbenzene 1a,
DABCO·(SO2)2, and 3-azido-2-methylbut-3-en-2-ol 2 in the
presence of 2.0 equivalents of 2,2,6,6-tetramethyl-1-
piperidinyloxy (TEMPO) under ultraviolet irradiation (Scheme 3,
eqn 2). The outcome showed that no desired product was
formed. In Scheme 1, we also proposed that C-C bond cleavage
For selected reviews, see: (a) G. Qiu, K. Zhou, L. Gao and J. Wu, Org.
Chem. Front., 2018, 5, 691; (b) K. Hofman, N. Liu and G. Manolikakes,
Chem. Eur. J., 2018, 24, 11852; (c) G. Liu, C. Fan and J. Wu, Org.
Biomol. Chem., 2015, 13, 1592; (d) G. Qiu, L. Lai, J. Cheng and J. Wu,
Chem. Commun., 2018, 54, 10405; (e) Qiu, K. Zhou and J. Wu, Chem.
Commun., 2018, 54, 12561; (f) A. S. Deeming, E. J. Emmett, C. S.
Richards-Taylor and M. C. Willis, Synthesis 2014, 46, 2701; (g) P.
Bisseret and N. Blanchard, Org. Biomol. Chem., 2013, 11, 5393. For
selected examples, see: (a) Z. Chen, N.-W. Liu, M. Bolte, H. Ren and G.
Manolikakes, Green Chem., 2018, 20, 3059; (b) Q. Lin, Y. Liu, Z. Xiao,
L. Zheng, X. Zhou, Y. Guo, Q.-Y. Chen, C. Zheng and C. Liu, Org. Chem.
Front., 2019, 6, 447; (c) X. Y. Qin, L. He, J. Li, W. J. Hao, S. J. Tu and B.
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 3
Please do not adjust margins

ChemComm
Page 4 of 4
Communication
ChemComm
Jiang, Chem. Commun., 2019, 55, 3227; (d) R. J. Reddy, A. H. Kumari, 11 (a) M. O. Anderson, J. Zhang, Y. Liu, C. Yao, P.-W. PVhieuwanArtaicnledOAn.linSe.
J. J. Kumar and J. B. Nanubolu, Adv. Synth. Catal., 2019, 361, 1587; (e)
L. Lu, C. Luo, H. Peng, H. Jiang, M. Lei and B. Yin, Org. Lett., 2019, 21,
Verkman, J. Med. Chem., 2012, 55, 5942; (b) Y. Zheng, M. Liu, G. Qiu,
W. Xie and J. Wu, Tetrahedron, 2019, 75, 1663.
DOI: 10.1039/D0CC00351D
2602; (f) Y. Meng, M. Wang and X. Jiang, Angew. Chem. Int. Ed., 2020, 12 (a) S. Diosdado, R. López and C. Palomo, Chem. Eur. J., 2014, 20, 6526;
59, 1346.
(b) B. L. Feringa, J. Chem. Soc., Chem. Commun., 1985, 466; (c) G. C.
Tsui, Q. Glenadel, C. Lau and M. Lautens, Org. Lett., 2011, 13, 208; (d)
T. M. Tagmose, F. Zaragoza, H. C. M. Boonen, A. Worsaae, J. P.
Mogensen, F. E. Nielsen, A. F. Jensen and J. B. Hansen, Bioorg. Med.
Chem., 2003, 11, 931.
5
(a) S.-T. Yuan, H. Zhou, L. Gao, J.-B. Liu and G. Qiu, Org. Lett., 2018,
20, 562; (b) S.-T. Yuan, Y.-H. Wang, J.-B. Liu and G. Qiu, Adv. Synth.
Catal., 2017, 359, 1981; (c) Y.-C. Wang, J.-B. Liu, H. Zhou, W. Xie, P.
Rojsitthisak
and
G.
Qiu,
J.
Org.
Chem.
2020,
DOI:10.1021/acs.joc.9b02590; (d) Y.-C. Wang, R.-X. Wang, G. Qiu, H. 13 (a) J. R. Donald, S. L. Berrell and Chem. Sci., 2019, 10, 5832; (b) C. Ma,
Zhou, W. Xie and J.-B. Liu, Org. Chem. Front., 2019, 6, 2471; (e) R. Liu,
M. Li, W. Xie, H. Zhou, Y. Zhang and G. Qiu, J. Org. Chem. 2019, 84,
11763; (f) W. Xie, Y. Wu, J. Zhang, Q. Mei, Y. Zhang, N. Zhu, Q. Liu and
H. Zhang, Eur. J. Med. Chem., 2018, 145, 35; (g) W. Xie, S. Xie, Y. Zhou,
X. Tang, J. Liu, W. Yang and M. Qiu, Eur. J. Med. Chem., 2014, 81, 22;
(h) W. Xie, H. Zhang, J. He, J. Zhang, Q. Yu, C. Luo and S. Li, Bioorg.
Med. Chem. Lett., 2017, 27, 530.
For recent selected examples, see: (a) Y. Zong, L. Lang, M. Yang, X. Li,
X. Fan and J. Wu, Org. Lett., 2019, 21, 1935; (b) J. Zhang, X. Li, W. Xie,
J. Wu and S. Ye, Org. Lett., 2019, 21, 4950; (c) X. Wang, M. Yang, W.
Xie, X. Fan and J. Wu, Chem. Commun., 2019, 55, 6010; (d) F.-S. He, Y.
Wu, X. Li, H. Xia and J. Wu, Org. Chem. Front., 2019, 6, 1873; (e) H.
Tang, Y. Kuang, J. Zeng, X. Li, W. Zhou and Y. Lu, RSC Adv. 2019, 9,
31474; (f) S. Ye, X. Li, W. Xie and J. Wu, Eur. J. Org. Chem. 2020, 15,
10.1002/ejoc.201900396; (g) X. Wang, Y. Kuang, S. Ye and J. Wu,
Chem. Commun., 2019, 55, 14962.
J.-Y. Zhou, Y.-Z. Zhang, Y. Jiao, G.-J. Mei and F. Shi, Chem. Asian J. 2018,
13, 2549; (c) X. Gong, J. Chen, X. Li, W. Xie and J. Wu, Chem. Asian J.
2018, 13, 2543; (d) T. Guo, Y. Liu, Y.-H. Zhao, P.-K. Zhang, S.-L. Han and
H.-M. Liu, Tetrahedron Lett., 2016, 57, 3920; (e) T. Guo, Y. Liu, Y.-H.
Zhao, P.-K. Zhang, S.-L. Han and H.-M. Liu, Tetrahedron Lett., 2016, 57,
4629; (f) S. Qiu, C. Wang, S. Xie, X. Huang, L. Chen, Y. Zhao and Z. Zeng,
Chem. Commun., 2018, 54, 11383; (g) Y.-H. Zhao, Y. Luo, Y. Zhu, H.
Wang, H. Zhou, H. Tan, Z. Zhou, Y.-C. Ma, W. Xie and Z. Tang, Synlett,
2018, 29, 773; (h) T. Guo, J.-J. Liang, S. Yang, H. Chen, Y.-N. Fu, S.-L.
Han and Y.-H. Zhao, Org. Biomol. Chem., 2018, 16, 6039; (i) Y.-H. Zhao,
Y. Li, Y. Long, Z. Zhou, Z. Tang, K. Deng and S. Zhang, Tetrahedron Lett.,
2017, 58, 1351; (j) T. Guo, X.-N. Wei, H.-Y. Wang, Y.-L. Zhu, Y.-H. Zhao
and Y.-C. Ma, Org. Biomol. Chem., 2017, 15, 9455; (k) Y.-H. Zhao, Y. Li,
M. Luo, Z. Tang and K. Deng, Synlett, 2016, 27, 2597; (l) Y.-H. Zhao, Y.
Li, T. Guo, Z. Tang, W. Xie and G. Zhao, Tetrahedron Lett., 2016, 57,
2257; (m) T. Guo, X.-N. Wei, Y. Liu, P.-K. Zhang and Y.-H. Zhao, Org.
Chem. Front., 2019, 6, 1414.
6
7
For selected examples, see: (a) S. E. Creutz, K. J. Lotito, G. C. Fu and J.
C. Peters, Science, 2012, 338, 647; (b) D. T. Ziegler, J. Choi, J. M. 14 (a) P. Li, J. Du, Y. Xie, M. Tao and Q. Zhang, ACS Sustainable Chem.
Muñoz-Molina, A. C. Bissember, J. C. Petersm and G. C. Fu, J. Am.
Chem. Soc., 2013, 135, 13107; (c) L. Li, W. Liu, H. Zeng, X. Mu, G. Cosa,
Z. Mi and C.-J. Li, J. Am. Chem. Soc., 2015, 137, 8328; (d) Y. C. Tan, J.
Eng., 2016, 4, 1139; (b) S.-S. Jin, H. Wang and H.-Y. Guo, Tetrahedron
Lett., 2013, 54, 2353; (c) C. Ma, F. Jiang, F.-T. Sheng, Y. Jiao, G.-J. Mei
and F. Shi, Angew. Chem. Int. Ed. 2019, 58, 3014.
M. Munoz-Molina, G. C. Fu and J. C. Peters, Chem. Sci., 2014, 5, 2831; 15 Y. Gao and Y. Lam, Adv. Synth. Catal., 2008, 350, 2937.
(e) J. A. Terrett, J. D. Cuthbertson, V. W. Shurtleff and D. W. C. 16 (a) M. O. Anderson, J. Zhang, Y. Liu, C. Yao, P.-W. Phuan and A. S.
MacMillan, Nature, 2015, 524, 330; (f) Z. Zuo, D. T. Ahneman, L. Chu,
J. A. Terrett, A. G. Doyle and D. W. C. MacMillan, Science, 2013, 339,
1593; (g) Z. Zuo, D. T. Ahneman, L. Chu, J. A. Terrett, A. G. Doyle and
D. W. C. MacMillan, Science, 2014, 345, 437; (h) Z. Zuo, H. Cong, W.
Li, J. Choi, G. C. Fu and D. W. C. MacMillan, J. Am. Chem. Soc., 2016,
138, 1832; (i) L. Chu, J. M. Lipshultz and D. W. C. MacMillan, Angew.
Chem. Int. Ed., 2015, 54, 7929.
Verkman, J. Med. Chem., 2012, 55, 5942; (b) M. Rahimizadeha, G.
Rajabzadehb, S.-M. Khatami, H. Eshghi and A. Shiri, J. Mol. Catal. A:
Chem., 2010, 323, 59; (c) R. D. Chakravarthy, V. Ramkumar and D. K.
Chand, Green Chem., 2014, 16, 2190; (d) M. Jereb, Green Chem., 2012,
14, 3047; (e) P. B. González, R. Lopez and C. Palomo, J. Org. Chem.,
2010, 75, 3920.
8
(a) X. Fu, Y. Meng, X. Li, M. Stepień and P. J. Chmielewski, Chem.
Commun., 2018, 54, 2510; (b) X. Li, Y. Meng, P. Yi, M. Stepień and P.
J. Chmielewski, Angew. Chem. Int. Ed., 2017, 56, 10810; (c) B. Liu, T.
Yoshida, X. Li, M. Stepień, H. Shinokubo and P. J. Chmielewski, Angew.
Chem. Int. Ed., 2016, 55, 13142; (d) Z. Deng, X. Li, M. Stepień and P. J.
Chmielewski, Chem. Eur. J., 2016, 22, 4231; (e) K. Deng, X. Li and H.
Huang, Electrochimica Acta., 2016, 204, 84; (f) B. Liu, X. Li, M. Stepień
and P. J. Chmielewski, Chem. Eur. J., 2015, 21, 7790; (g) B. Liu, H. Fang,
X. Li, W. Cai, L. Bao, M. Rudolf, F. Plass, L. Fan, X. Lu and D. M. Guldi,
Chem. Eur. J., 2015, 21, 746; (h) B. Liu, X. Li, J. Maciołek, M. Stepień
and P. J. Chmielewski, J. Org. Chem., 2014, 79, 3129; (i) B. Liu, X. Li, X.
Xu, M. Stepień and P. J. Chmielewski, J. Org. Chem., 2013, 78, 1354;
(j) X. Li, B. Liu, P. J. Chmielewski and X. Xu, J. Org. Chem., 2012, 77,
8206; (k) X. Li, B. Liu, X. Yu, P. Yi, R. Yi and P. J. Chmielewski, J. Org.
Chem., 2012, 77, 2431; (l) X. Li, B. Liu, P. Yi, R. Yi, X. Yu and P. J.
Chmielewski, J. Org. Chem., 2011, 76, 2345.
9
(a) A. M. Mfuh, J. D. Doyle, B. Chhetri, H. D. Arman and O. V. Larionov,
J. Am. Chem. Soc., 2016, 138, 2985; (b) G. Qiu, Y. Li and J. Wu, Org.
Chem. Front., 2016, 3, 1011; (c) W. Liu, L. Li and C.-J. Li, Nat. Commun.,
2015, 6, 6526; (d) L. Li, W. Liu, H. Zeng, X. Mu, G. Cosa, Z. Mi and C.-J.
Li, J. Am. Chem. Soc., 2015, 137, 8328; (e) Y. Li, D. Zheng, Z. Li and J.
Wu, Org. Chem. Front., 2016, 3, 574; (f) X. Gong, Y. Ding, X. Fan and J.
Wu, Adv. Synth. Catal., 2017, 359, 2999; (g) P. Kamal Walia, M. Kumar
and V. Bhalla, ACS Omega 2018, 3, 1983; (h) X. Yang, W. Liu, L. Li, W.
Wei and C.-J. Li, Chem. Eur. J., 2016, 22, 15252.
10 K. H. Goütz, S. M. Hacker, D. Mayer, J.-N. Dürig, S. Stenger and A.
Marx, ACS Chem. Biol., 2017, 12, 2682.
4 | J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx