Silver-Catalyzed Cascade Cyclization Reaction of Isocyanides with Sulfoxonium Ylides: Synthesis of 3-Aminofurans and 4-Aminoquinolines

Article abstract of DOI:10.1021/acs.orglett.0c02835

A silver-catalyzed cascade cyclization reaction of isocyanides with sulfoxonium ylides has been developed for the first time. This reaction provides a new and efficient method for the construction of highly functionalized 3-aminofurans and 4-aminoquinolines from readily available starting materials in a single step.

Full text of DOI:10.1021/acs.orglett.0c02835

pubs.acs.org/OrgLett
Letter
Silver-Catalyzed Cascade Cyclization Reaction of Isocyanides with
Sulfoxonium Ylides: Synthesis of 3‑Aminofurans and
4‑Aminoquinolines
Yong-Xin Liang, Ming Yang, Bo-Wen He, and Yu-Long Zhao*
Cite This: https://dx.doi.org/10.1021/acs.orglett.0c02835
Read Online
sı
*
Metrics & More
Article Recommendations
Supporting Information
ACCESS
ABSTRACT: A silver-catalyzed cascade cyclization reaction of
isocyanides with sulfoxonium ylides has been developed for the first
time. This reaction provides a new and efficient method for the
construction of highly functionalized 3-aminofurans and 4-amino-
quinolines from readily available starting materials in a single step.
he furan scaffold is an important structural unit abundant
Tin many biologically active natural products, pharma-
ceuticals, and agrochemicals.1 Thus, considerable efforts have
been developed to access polysubstituted furans.2 As important
members of these families, amino-substituted furans not only
show potential biological activities3 but also are useful and
important intermediates with significant applications in organic
synthesis.4 Despite their broad utility, the availability of
methods for the construction of 3-aminofurans is limited.
Several methods have been reported for their synthesis, such as
direct coupling reaction of 3-bromofuran with amines,5
cyclization reactions of dibenzoylethylene or γ-hydroxy α,β-
unsaturated acetylenic ketones with amines,6 base-promoted
cyclization reactions of α-cyanoketone with ethyl glyoxylate7 or
enaminones with aldehydes,8 and base-mediated three-
component reaction of thiazolium salts, aldehydes, and
dimethyl acetylenedicarboxylate.9 However, these reactions
suffer from limited substrate scope, lack of readily available
precursors, tedious synthetic procedures, or requirement for
the use of stoichiometric amounts of strong bases. Recently,
transition-metal-catalyzed reactions, including the gold-cata-
lyzed three-component reaction of phenylglyoxal derivatives,
secondary amines, and terminal alkynes;10 the rhodium/gold-
cocatalyzed domino reaction of N-sulfonyl-1,2,3-riazoles with
propargyl alcohols;11 and the zinc-catalyzed [4 + 1] annulation
of alkylthio-substituted enaminones with sulfur ylides,12 have
become a convenient and promising method for the synthesis
of 3-aminofurans. Despite great progress, exploiting new
transition-metal-catalyzed synthesis of 3-aminofurans from
readily available precursors is highly desired.
preparing 4-aminoquinolines bearing 2-aryl functionalities have
been developed.15 In 2013, Orru and co-workers reported a
Pd-catalyzed oxidative cyclization of tert-butyl isocyanide with
N-arylimines to afford the 4-aminoquinolines. However, this
method was limited to tert-butyl isocyanide and low yields.15e
Thus, the development of an efficient and simple method for
the construction of 4-aminoquinolines bearing 2-aryl function-
alities is still in need.
Isocyanides are extraordinarily versatile and powerful
building blocks due to their unique reactivity toward
electrophiles, nucleophiles, and radicals.16 In this field,
transition-metal-catalyzed coupling reactions of isocyanides
with various carbene precursors, such as diazo compounds17
and organic azides,18 have become a convenient and promising
approach to access various N-containing compounds. In
addition, as a kind of alternative carbene analogues,
sulfonium/sulfoxonium ylides have been widely applied in
transition-metal-catalyzed C−H activation due to their easy
accessibility, stability, and diverse reactivity.19 Aside from these
transformations, transition-metal-catalyzed cross-coupling re-
actions of sulfoxonium ylides via the carbene insertion process
were also sporadically reported in recent years.20 However, to
the best of our knowledge, the transition-metal-catalyzed
carbene-transfer reaction of sulfoxonium ylides with isocya-
nides has not been reported. As part of our continuing interest
in the applications of diazo compounds21 and isocyanides,22
herein we report a novel silver-catalyzed coupling cyclization of
isocyanides with sulfoxonium ylides for the first time. This
reaction offers a new and efficient strategy for the synthesis of
On the other hand, quinoline compounds, as an important
heterocyclic skeleton, are widely present in natural products
and pharmaceuticals with a broad range of bioactivities.
Among them, 4-aminoquinolines have attracted much
attention because of their effective drug activity.13 Especially,
4-aminoquinolines bearing 2-aryl functionalities show promise
as non-nucleoside HIV-1 inhibitors.14 Many methods for
Received: August 24, 2020
https://dx.doi.org/10.1021/acs.orglett.0c02835
© XXXX American Chemical Society
Org. Lett. XXXX, XXX, XXX−XXX
A

Organic Letters
pubs.acs.org/OrgLett
Letter
highly functionalized 3-aminofurans and 4-aminoquinolines in
a single step from readily available starting materials.
Initially, the reaction of 4-isocyanobiphenyl 1a with
sulfoxonium ylide 2a was investigated to optimize the reaction
conditions (Table 1). We found that, under the catalysis of
Scheme 1. Scope of the Reaction with Respect to the
Isocyanides 1a−q
a b
,
a b
,
Table 1. Optimization of Reaction Conditions
b
entry
catalyst (mol %)
1a:2a
solvent
t/h
yield (%)
42
1
2
3
4
5
6
7
8
9
10
11
12
13
14
AgSbF6 (10)
AgSbF6 (20)
AgSbF6 (30)
AgSbF6 (20)
AgSbF6 (20)
Ag(TFA) (20)
AgOTf (20)
Ag2CO3 (20)
AgOAc (20)
AgNO3 (20)
AgSbF6 (20)
AgSbF6 (20)
AgSbF6 (20)
AgSbF6 (20)
1:2
1:2
1:2
1:1
1:3
1:2
1:2
1:2
1:2
1:2
1:2
1:2
1:2
1:2
toluene
toluene
toluene
toluene
toluene
toluene
toluene
toluene
toluene
toluene
m-xylene
PhCl
10
10
10
10
10
10
10
10
10
10
10
12
12
12
c
73
54
27
48
11
24
---
---
10
30
20
21
---
DCE
DMF
a
Reaction conditions: 1a (0.2 mmol), 2a (0.4 mmol), catalyst (0.02−
b
0.06 mmol), solvent (2.0 mL), at 110 °C for 10−12 h. Estimated by
1H NMR spectroscopy using 1,3,5-trimethoxybenzene as an internal
c
standard. Isolated yield.
a
AgSbF6 (10 mol %) in toluene at 110 °C for 10 h, the reaction
of 1a (0.2 mmol) with 2a (0.4 mmol) resulted in 3-aminofuran
3aa in 42% yield (entry 1). To our delight, the yield of 3aa was
raised to 73% in the presence of AgSbF6 (20 mol %) (entry 2).
Decreasing the ratio of 2a/1a to 1/1, the product 3aa was
obtained in 27% yield along with the recovery of 4-
isocyanobiphenyl 1a in 38% yield (entry 4). Interestingly,
increasing the amount of AgSbF6 and the ratio of 2a/1a led to
lower yields of 3aa (entries 3 and 5). Other silver catalysts
such as Ag(TFA), AgOTf, Ag2CO3, AgOAc, and AgNO3 were
less effective (entries 6, 7, and 10) or ineffective (entries 8 and
9). In addition, solvent screening revealed that solvents have a
great effect on the reaction. Among the solvents tested, toluene
seemed to be the best choice. Other solvents, such as m-xylene,
PhCl, and DCE, gave lower product yields (entries 11−13).
No desired product 3aa was observed (TLC) when the
reaction was performed in DMF (entry 14).
With the optimal reaction condition in hand, the scope of
the [3 + 1 + 1] cyclization reaction was examined with respect
to isocyanides 1, and the results are summarized in Scheme 1.
All selected aryl isocyanides 1a−o, bearing phenyl, electron-
rich, electron-deficient aryl, biphenyl, and 2-naphthyl R groups,
reacted smoothly with sulfoxonium ylide 2a to give the
corresponding 3-aminofurans 3a−oa in good to high yields. In
contrast, aryl isocyanides 1f−m and 1o with electron-
withdrawing groups on the phenyl ring and naphthalenyl
isocyanide 1n gave relatively higher yields. It is noteworthy
that the vinyl isocyanide 1p can be tolerated, with the
Reaction conditions: 1 (0.2 mmol), 2a (0.4 mmol), AgSbF6 (0.04
b
mmol), toluene (2.0 mL), at 110 °C for 8−12 h. Isolated yield.
generation of 3pa in 40% yield. More importantly, benzyl
isocyanide 1q was found to be a suitable coupling partner,
generating the desired 3-aminofuran 3qa in 42% yield.
However, no desired product was observed when tert-butyl
isocyanide was employed as the partner (Scheme 1). In
addition, we found that the [3 + 1 + 1] annulation reaction is
easy to scale-up. A scale-up reaction of 1g (4.0 mmol) and 2a
(8.0 mmol) was carried out for 10 h under otherwise identical
conditions as above, furnishing 1.14 g of the desired product
3ga in 71% isolated yield.
Next, the scope of sulfoxonium ylides 2 was explored under
the optimal conditions. As shown in Scheme 2, various
benzoyl-substituted sulfoxonium ylides 2b−j bearing a variety
of functional groups, such as electron-donating groups (CH3, t-
Bu, OMe) and electron-withdrawing groups (Cl, Br, F, CF3) at
the para, ortho, and meta positions of the phenyl ring, reacted
smoothly with 1a to produce the corresponding 3-aminofurans
3ab−j in good to high yields. Similarly, thienyl-substituted
sulfoxonium ylide 2k was also compatible in this reaction and
produced the desired product 3ak in 53% yield. Notably, in the
case of alkanoyl sulfoxonium ylide 2l, the [3 + 1 + 1]
cyclization reaction also worked well, affording the desired
product 3al in 65% yield (Scheme 2). In addition, we found
that, when two different sulfoxonium ylides 2a (0.2 mmol) and
B
https://dx.doi.org/10.1021/acs.orglett.0c02835
Org. Lett. XXXX, XXX, XXX−XXX

Organic Letters
pubs.acs.org/OrgLett
Letter
was obtained in 43% yield (Scheme 4). To our delight, after a
series of optimization steps, we found that, under the catalysis
Scheme 2. Scope of the Reaction with Respect to the
Sulfoxonium Ylides 2b−l
a b
,
a b
,
Scheme 4. Synthesis of 4-Aminoquinolines 5
a
Reaction conditions: 1 (0.2 mmol), 4a−f (0.2 mmol), AgTFA (0.04
b
mmol), toluene (2.0 mL), at 100 °C for 10−24 h. Isolated yield.
of AgTFA (20 mol %) in toluene at 100 °C for 24 h, the
cascade cyclization reaction of 1c with 4a resulted in 4-
aminoquinoline 5a in 76% yield. Similarly, N-aryl imidoyl
sulfoxonium ylides 4b−e bearing either electron-donating or
electron-withdrawing R1 groups on the aromatic rings could
react efficiently with isocyanide 1c to produce 4-aminoquino-
lines 5b−e in good yields. When the N-aryl imidoyl
sulfoxonium ylide 4f bearing the Br group at the meta position
of the aromatic ring was employed as a coupling partner, the
product 5f was produced in 65% yield. In addition, aryl
isocyanides 1d and 1i with electron-rich and electron-deficient
substituents also participated efficiently in this transformation,
giving the 4-aminoquinolines 5g and 5h in 72% and 56%
yields, respectively. More importantly, tert-butyl isocyanide 1r
was also tolerant, with the generation of 4-aminoquinolines 5i
in 75% yield (Scheme 4).
a
Reaction conditions: 1a (0.2 mmol), 2b−l (0.4 mmol), AgSbF6
b
(0.04 mmol), toluene (2.0 mL), at 110 °C for 8−12 h. Isolated yield.
2f (0.2 mmol) were treated with 1a (0.2 mmol) under the
optimized reaction conditions, 3-aminofurans 3aa and 3af were
produced in 21% and 17% yields along with the mixture of
3am and 3an in 26% yield, respectively (Scheme 3).
Scheme 3. Reaction of 1a with Two Different Sulfoxonium
Ylides 2a and 2f
On the basis of the above experimental results together with
related reports,16−20,24 a possible mechanism for the formation
of 3 and 5 is proposed in Scheme 5. Initially, isocyanides 1
coordinate with AgSbF6 or AgTFA to form intermediate A,
which reacts with sulfoxonium ylides 2 or 4 to give
intermediate B. Subsequently, intermediate C, generated by
the elimination of DMSO and silver, was trapped by
sulfoxonium ylides 2a−l to produce intermediate D.
Intermediate D undergoes intramolecular nucleophilic sub-
stitution reaction to generate intermediate E along with the
elimination of DMSO. Finally, intermediate E undergoes
intramolecular cyclization to form F, followed by the 1,3-
proton shift to give the corresponding 3-aminofurans 3. In the
case of N-aryl imidoyl sulfoxonium ylides 4a−f, the ketenimine
intermediate G undergoes an intramolecular Friedel−Crafts
cyclization or electrocyclization, followed by the protonation to
produce the 4-aminoquinolines 5 (Scheme 5).
On the basis of the above experimental results, along with
the consideration of the structural feature of N-aryl imidoyl
sulfoxonium ylides,23 we reasoned that the ketenimine
intermediate generated from the reaction of N-aryl imidoyl
sulfoxonium ylides 4a−f and isocyanides 1 can undergo an
intramolecular cyclization to afford 4-aminoquinolines. As
expected, when the reaction of 1c (0.2 mmol) and N-phenyl
imidoyl sulfoxonium ylide 4a (0.2 mmol) was carried out
under identical conditions as above, the 4-aminoquinoline 5a
C
https://dx.doi.org/10.1021/acs.orglett.0c02835
Org. Lett. XXXX, XXX, XXX−XXX

Organic Letters
pubs.acs.org/OrgLett
Letter
Chemistry, Northeast Normal University, Changchun 130024,
China
Scheme 5. Proposed Mechanism for the Formation of 3 and
5
Complete contact information is available at:
https://pubs.acs.org/10.1021/acs.orglett.0c02835
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
Financial support of this research by the National Natural
Sciences Foundation of China (21871044 and 21472017) and
Natural Sciences Foundation of Jilin Province
(20190201073JC) is greatly acknowledged.
REFERENCES
■
(1) (a) Goodman, K. B.; Bury, M. J.; Cheung, M.; Cichy-Knight, M.
A.; Dowdell, S. E.; Dunn, A. K.; Lee, D.; Lieby, J. A.; Moore, M. L.;
Scherzer, D. A.; Sha, D.; Suarez, D. P.; Murphy, D. J.; Harpel, M. R.;
Manas, E. S.; McNulty, D. E.; Annan, R. S.; Matico, R. E.; Schwartz,
B. K.; Trill, J. J.; Sweitzer, T. D.; Wang, D. Y.; Keller, P. M.; Krawiec,
J. A.; Jaye, M. C. Bioorg. Med. Chem. Lett. 2009, 19, 27. (b) Bunz, U.
H. F. Angew. Chem., Int. Ed. 2010, 49, 5037. (c) Rao, A. U.; Xiao, D.;
Huang, X.; Zhou, W.; Fossetta, J.; Lundell, D.; Tian, F.; Trivedi, P.;
Aslanian, R.; Palani, A. Bioorg. Med. Chem. Lett. 2012, 22, 1068.
(d) Hasegawa, F.; Niidome, K.; Migihashi, C.; Murata, M.; Negoro,
T.; Matsumoto, T.; Kato, K.; Fujii, A. Bioorg. Med. Chem. Lett. 2014,
24, 4266.
In summary, we have developed a silver-catalyzed cascade
cyclization reaction of isocyanides with sulfoxonium ylides for
the first time. This new reaction provides a novel and efficient
method for the synthesis of 3-aminofurans and 4-aminoquino-
lines in a single operation. This protocol features readily
available starting materials, broad substrate scope, good to high
yields, and good functional group tolerance. Further studies on
the coupling reactions of isocyanides with sulfoxonium ylides
are in progress.
(2) (a) Zhao, Y.; Li, S.; Zheng, X.; Tang, J.; She, Z.; Gao, G.; You, J.
Angew. Chem., Int. Ed. 2017, 56, 4286. (b) Gharpure, S. J.; Prasath, P.
V.; Shelke, Y. G. Org. Lett. 2019, 21, 223. (c) He, X.; Tang, Y.; Wang,
Y.; Chen, J. B.; Xu, S.; Dou, J.; Li, Y. Angew. Chem., Int. Ed. 2019, 58,
10698. (d) Xia, Y.; Xia, Y.; Ge, R.; Liu, Z.; Xiao, Q.; Zhang, Y.; Wang,
J. Angew. Chem., Int. Ed. 2014, 53, 3917. (e) Keay, B. A. Chem. Soc.
Rev. 1999, 28, 209. (f) Roslan, I. I.; Sun, J.; Chuah, G.-K.; Jaenicke, S.
Adv. Synth. Catal. 2015, 357, 719. (g) Lou, J.; Wang, Q.; Wu, K.; Wu,
P.; Yu, Z. Org. Lett. 2017, 19, 3287. (h) Liu, Z. T.; Hu, X. P. Chem.
Commun. 2018, 54, 14100. (i) Yuan, Y.; Tan, H.; Kong, L.; Zheng, Z.;
Xu, M.; Huang, J.; Li, Y. Org. Biomol. Chem. 2019, 17, 2725. (j) Li, H.
L.; Wang, Y.; Sun, P. P.; Luo, X.; Shen, Z.; Deng, W. P. Chem. - Eur. J.
2016, 22, 9348. (k) Li, Q.; He, X.; Tao, J.; Xie, M.; Wang, H.; Li, R.;
Shang, Y. Adv. Synth. Catal. 2019, 361, 1874. (l) Mao, S.; Zhu, X. Q.;
Gao, Y. R.; Guo, D. D.; Wang, Y. Q. Chem. - Eur. J. 2015, 21, 11335.
(m) Wang, Q.; Liu, Z.; Lou, J.; Yu, Z. Org. Lett. 2018, 20, 6007.
(3) (a) Lee, S.; Kim, T.; Lee, B. H.; Yoo, S.; Lee, K.; Yi, K. Y. Bioorg.
Med. Chem. Lett. 2007, 17, 1291. (b) Wang, S.; Fang, K.; Dong, G.;
Chen, S.; Liu, N.; Miao, Z.; Yao, J.; Li, J.; Zhang, W.; Sheng, C. J. Med.
Chem. 2015, 58, 6678. (c) Srimongkolpithak, N.; Sundriyal, S.; Li, F.;
Vedadi, M.; Fuchter, M. J. MedChemComm 2014, 5, 1821. (d) Wolter,
F. E.; Schneider, K.; Davies, B. P.; Socher, E. R.; Nicholson, G.; Seitz,
O.; Sussmuth, R. D. Org. Lett. 2009, 11, 2804.
ASSOCIATED CONTENT
* Supporting Information
■
sı
The Supporting Information is available free of charge at
https://pubs.acs.org/doi/10.1021/acs.orglett.0c02835.
Experimental procedures, full spectroscopic data, and 1H
and 13C NMR spectra of all compounds (PDF)
Accession Codes
CCDC 1994946 contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge
via www.ccdc.cam.ac.uk/data_request/cif, or by emailing
data_request@ccdc.cam.ac.uk, or by contacting The Cam-
bridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
AUTHOR INFORMATION
Corresponding Author
■
Yu-Long Zhao − Jilin Province Key Laboratory of Organic
Functional Molecular Design & Synthesis, Faculty of Chemistry,
Northeast Normal University, Changchun 130024, China;
orcid.org/0000-0001-6577-1074; Email: zhaoyl351@
nenu.edu.cn
(4) (a) Kalaitzakis, D.; Triantafyllakis, M.; Alexopoulou, I.; Sofiadis,
M.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2014, 53, 13201.
(b) Moss, T. A. Tetrahedron Lett. 2013, 54, 993. (c) Montagnon, T.;
Tofi, M.; Vassilikogiannakis, G. Acc. Chem. Res. 2008, 41, 1001.
(d) Scesa, P.; Wangpaichitr, M.; Savaraj, N.; West, L.; Roche, S. P.
Angew. Chem., Int. Ed. 2018, 57, 1316.
Authors
(5) Hooper, M. W.; Utsunomiya, M.; Hartwig, J. F. J. Org. Chem.
2003, 68, 2861.
(6) Erdenebileg, U.; Hostmark, I.; Polden, K.; Sydnes, L. K. J. Org.
Chem. 2014, 79, 1213.
(7) Redman, A. M.; Dumas, J.; Scott, W. J. Org. Lett. 2000, 2, 2061.
(8) Kong, L.; Shao, Y.; Li, Y.; Liu, Y.; Li, Y. J. Org. Chem. 2015, 80,
12641.
(9) (a) Ma, C.; Yang, Y. Org. Lett. 2005, 7, 1343. (b) Ma, C.; Ding,
H.; Wu, G.; Yang, Y. J. Org. Chem. 2005, 70, 8919.
(10) Li, J.; Liu, L.; Ding, D.; Sun, J.; Ji, Y.; Dong, J. Org. Lett. 2013,
15, 2884.
Yong-Xin Liang − Jilin Province Key Laboratory of Organic
Functional Molecular Design & Synthesis, Faculty of
Chemistry, Northeast Normal University, Changchun 130024,
China
Ming Yang − Jilin Province Key Laboratory of Organic
Functional Molecular Design & Synthesis, Faculty of
Chemistry, Northeast Normal University, Changchun 130024,
China
Bo-Wen He − Jilin Province Key Laboratory of Organic
Functional Molecular Design & Synthesis, Faculty of
D
https://dx.doi.org/10.1021/acs.orglett.0c02835
Org. Lett. XXXX, XXX, XXX−XXX

Organic Letters
pubs.acs.org/OrgLett
Letter
(11) Cheng, X.; Yu, Y.; Mao, Z.; Chen, J.; Huang, X. Org. Biomol.
Chem. 2016, 14, 3878.
(12) He, Y.; Lou, J.; Zhou, Y.-G.; Yu, Z. Chem. - Eur. J. 2020, 26,
4941.
(13) (a) Barnett, D. S.; Guy, R. K. Chem. Rev. 2014, 114, 11221.
(b) Krapf, M. K.; Wiese, M. J. Med. Chem. 2016, 59, 5449. (c) Zheng,
X.; Liang, C.; Wang, L.; Wang, B.; Liu, Y.; Feng, S.; Wu, J. Z.; Gao, L.;
Feng, L.; Chen, L.; Guo, T.; Shen, H. C.; Yun, H. J. Med. Chem. 2018,
61, 10228. (d) Zheng, X.; Gao, L.; Wang, L.; Liang, C.; Wang, B.; Liu,
Y.; Feng, S.; Zhang, B.; Zhou, M.; Yu, X.; Xiang, K.; Chen, L.; Guo,
T.; Shen, H. C.; Zou, G.; Wu, J. Z.; Yun, H. J. Med. Chem. 2019, 62,
6003.
(21) For selected recent examples, see: (a) Bu, X.-B.; Wang, Z.;
Wang, X.-D.; Meng, X.-H.; Zhao, Y.-L. Adv. Synth. Catal. 2018, 360,
2945. (b) Li, L.; Chen, J.-J.; Li, Y.-J.; Bu, X.-B.; Liu, Q.; Zhao, Y.-L.
Angew. Chem., Int. Ed. 2015, 54, 12107. (c) Zhang, L.; Chen, J.-J.; Liu,
S.-S.; Liang, Y.-X.; Zhao, Y.-L. Adv. Synth. Catal. 2018, 360, 2172.
(d) Bu, X.-B.; Yu, Y.; Li, B.; Zhang, L.; Chen, J.-J.; Zhao, Y.-L. Adv.
Synth. Catal. 2017, 359, 351. (e) Li, Y.-J.; Li, X.; Zhang, S.-X.; Zhao,
Y.-L.; Liu, Q. Chem. Commun. 2015, 51, 11564. (f) Yu, Y.; Zhang, Y.;
Wang, Z.; Liang, Y.-X.; Zhao, Y.-L. Org. Chem. Front. 2019, 6, 3657.
(g) Liang, Y.-X.; Meng, X.-H.; Yang, M.; Haroon, M.; Zhao, Y.-L.
Chem. Commun. 2019, 55, 12519. (h) Sun, R.; Du, Y.; Tian, C.; Li, L.;
Wang, H.; Zhao, Y.-L. Adv. Synth. Catal. 2019, 361, 5684.
(22) For selected recent examples, see: (a) Zhang, L.; Liu, T.; Wang,
Y. M.; Chen, J.; Zhao, Y. L. Org. Lett. 2019, 21, 2973. (b) Wang, Z.;
Meng, X.-H.; Liu, P.; Hu, W.-Y.; Zhao, Y.-L. Org. Chem. Front. 2020,
7, 126. (c) Liu, L.; Li, L.; Mao, S.; Wang, X.; Zhou, M.-D.; Zhao, Y.-
L.; Wang, H. Chem. Commun. 2020, 56, 7665. (d) Bu, X.-B.; Zhang,
Z.-X.; Peng, Q.-Q.; Xu, X.; Zhao, Y.-L. J. Org. Chem. 2019, 84, 53.
(23) Caiuby, C. A. D.; de Jesus, M. P.; Burtoloso, A. C. B. J. Org.
Chem. 2020, 85, 7433.
́
(14) Kireev, D. B.; Chretien, J. R.; Raevsky, O. A. Eur. J. Med. Chem.
1995, 30, 395.
(15) For selected recent examples, see: (a) Oh, K. H.; Kim, J. G.;
Park, J. K. Org. Lett. 2017, 19, 3994. (b) Rode, N. D.; Arcadi, A.;
Chiarini, M.; Marinelli, F.; Portalone, G. Adv. Synth. Catal. 2017, 359,
3371. (c) Collet, J. W.; Ackermans, K.; Lambregts, J.; Maes, B. U. W.;
Orru, R. V. A.; Ruijter, E. N. J. Org. Chem. 2018, 83, 854. (d) Shi, L.;
Pan, L.; Li, Y.; Liu, Q. Adv. Synth. Catal. 2017, 359, 2457. (e) Vlaar,
T.; Maes, B. U. W.; Ruijter, E.; Orru, R. V. A. Chem. Heterocycl.
Compd. 2013, 49, 902.
(16) For recent reviews, see: (a) Boyarskiy, V. P.; Bokach, N. A.;
Luzyanin, K. V.; Kukushkin, V. Y. Chem. Rev. 2015, 115, 2698.
(b) Zhang, B.; Studer, A. Chem. Soc. Rev. 2015, 44, 3505. (c) Song, B.;
Xu, B. Chem. Soc. Rev. 2017, 46, 1103. (d) Qiu, G.; Ding, Q.; Wu, J.
Chem. Soc. Rev. 2013, 42, 5257. (e) Lang, S. Chem. Soc. Rev. 2013, 42,
4867.
(24) (a) Tsuruoka, H.; Kasai, S.; Takebayashi, M.; Ibata, T. Chem.
Lett. 1976, 5, 315. (b) Cho, S. H.; Chang, S. Angew. Chem., Int. Ed.
2008, 47, 2836. (c) Baumann, M.; Baxendale, I. R. J. Org. Chem. 2015,
80, 10806. (d) Liu, L.; Wang, J.; Zhou, H. J. Org. Chem. 2015, 80,
4749.
(17) (a) Vlaar, T.; Ruijter, E.; Maes, B. U. W.; Orru, R. V. A. Angew.
Chem., Int. Ed. 2013, 52, 7084. (b) Chen, G.-S.; Chen, S.-J.; Luo, J.;
Mao, X.-Y.; Chan, A. S.-C.; Sun, R. W.-Y.; Liu, Y.-L. Angew. Chem., Int.
Ed. 2020, 59, 614. (c) Yan, X.; Liao, J.; Lu, Y.; Liu, J.; Zeng, Y.; Cai,
Q. Org. Lett. 2013, 15, 2478. (d) Zhou, F.; Ding, K.; Cai, Q. Chem. -
Eur. J. 2011, 17, 12268. (e) He, X.; Yu, Z.; Zuo, Y.; Yang, C.; Shang,
Y. Org. Biomol. Chem. 2017, 15, 7127. (f) Dai, Q.; Jiang, Y.; Yu, J.-T.;
Cheng, J. Chem. Commun. 2015, 51, 16645.
(18) For selected recent examples, see: (a) Zhang, Z.; Huang, B.;
Qiao, G.; Zhu, L.; Xiao, F.; Chen, F.; Fu, B.; Zhang, Z. Angew. Chem.,
Int. Ed. 2017, 56, 4320. (b) Gu, Z.; Liu, Y.; Wang, F.; Bao, X.; Wang,
S.; Ji, S. ACS Catal. 2017, 7, 3893. (c) Beaumier, E. P.; McGreal, M.
E.; Pancoast, A. R.; Wilson, R. H.; Moore, J. T.; Graziano, B. J.;
Goodpaster, J. D.; Tonks, I. A. ACS Catal. 2019, 9, 11753. (d) Ansari,
A. J.; Wani, A. A.; Maurya, A. K.; Verma, S.; Agnihotri, V. K.; Sharon,
A.; Bharatam, P. V.; Sawant, D. M. Chem. Commun. 2019, 55, 14825.
(e) Sawant, D. M.; Sharma, S.; Pathare, R. S.; Joshi, G.; Kalra, S.;
Sukanya, S.; Maurya, A. K.; Metre, R. K.; Agnihotri, V. K.; Khan, S.;
Kumar, R.; Pardasani, R. T. Chem. Commun. 2018, 54, 11530.
(19) For selected recent examples, see: (a) Clare, D.; Dobson, B. C.;
Inglesby, P. A.; Aïssa, C. Angew. Chem., Int. Ed. 2019, 58, 16198.
(b) Barday, M.; Janot, C.; Halcovitch, N. R.; Muir, J.; Aissa, C. Angew.
Chem., Int. Ed. 2017, 56, 13117. (c) Halskov, K. S.; Witten, M. R.;
Hoang, G. L.; Mercado, B. Q.; Ellman, J. A. Org. Lett. 2018, 20, 2464.
(d) Chen, X.; Wang, M.; Zhang, X.; Fan, X. Org. Lett. 2019, 21, 2541.
(e) Jia, Q.; Kong, L.; Li, X. Org. Chem. Front. 2019, 6, 741. (f) Wu, C.;
Zhou, J.; He, G.; Li, H.; Yang, Q.; Wang, R.; Zhou, Y.; Liu, H. Org.
Chem. Front. 2019, 6, 1183. (g) Xu, G.-D.; Huang, K. L.; Huang, Z.-Z.
Adv. Synth. Catal. 2019, 361, 3318. (h) Yu, J.; Wen, S.; Ba, D.; Lv, W.;
Chen, Y.; Cheng, G. Org. Lett. 2019, 21, 6366.
(20) (a) Neuhaus, J. D.; Bauer, A.; Pinto, A.; Maulide, N. Angew.
Chem., Int. Ed. 2018, 57, 16215. (b) Hoang, G. L.; Ellman, J. A.
Tetrahedron 2018, 74, 3318. (c) Zhang, L.; Chen, J.; Chen, J.; Jin, L.;
Zheng, X.; Jiang, X.; Yu, C. Tetrahedron Lett. 2019, 60, 1053. (d) Xu,
Y.; Zhou, X.; Zheng, G.; Li, X. Org. Lett. 2017, 19, 5256. (e) You, C.;
Pi, C.; Wu, Y.; Cui, X. Adv. Synth. Catal. 2018, 360, 4068. (f) Huang,
Y.; Lyu, X.; Song, H.; Wang, Q. Adv. Synth. Catal. 2019, 361, 5272.
(g) Chen, P.; Nan, J.; Hu, Y.; Ma, Q.; Ma, Y. Org. Lett. 2019, 21,
4812. (h) Oh, H.; Han, S.; Pandey, A. K.; Han, S. H.; Mishra, N. K.;
Kim, S.; Chun, R.; Kim, H. S.; Park, J.; Kim, I. S. J. Org. Chem. 2018,
83, 4070.
E
https://dx.doi.org/10.1021/acs.orglett.0c02835
Org. Lett. XXXX, XXX, XXX−XXX