One-Pot Synthesis of 4-Aryl-NH-1,2,3-Triazoles through Three-Component Reaction of Aldehydes, Nitroalkanes and NaN3

Article abstract of DOI:10.1002/cjoc.201700367

A one-pot three-component reaction of aldehydes, nitroalkanes and NaN₃ for the synthesis of NH-1,2,3-triazoles has been developed. The reaction provides a safe, efficient and step-economic approach for the synthesis of various NH-1,2,3-triazoles in good to excellent yields.

Full text of DOI:10.1002/cjoc.201700367

COMMUNICATION
DOI: 10.1002/cjoc.201700367
One-Pot Synthesis of 4-Aryl-NH-1,2,3-Triazoles through
Three-Component Reaction of Aldehydes, Nitroalkanes and
NaN3
Rongrong Hui,a Mina Zhao,a,b Ming Chen,a Zhihui Ren,a and Zhenghui Guan*,a
a Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education,
Department of Chemistry & Materials Science, Northwest University, Xi'an, Shaanxi 710127, China
b Shaanxi Key Laboratory of Phytochemistry, College of Chemistry and Chemical Engineering,
Baoji University of Arts and Sciences, Baoji, Shaanxi 721013, China
A one-pot three-component reaction of aldehydes, nitroalkanes and NaN3 for the synthesis of NH-1,2,3-triazoles
has been developed. The reaction provides a safe, efficient and step-economic approach for the synthesis of various
NH-1,2,3-triazoles in good to excellent yields.
Keywords aldehydes, sodium azide, one-pot, three-component reaction, NH-1,2,3-triazoles
Introduction
Organo-catalyzed three-component condensation reac-
tion to synthesize 1,4,5-trisubstituted 1,2,3-triazoles has
also been developed.[10] However, most of these strate-
gies are restricted to employing terminal alkynes and
organic azides as the substrates to synthesize N-substi-
tuted 1,2,3-triazoles. Versatile and practical methods for
the synthesis of valuable NH-1,2,3-triazoles remain
highly desirable.
Owing to the unique chemical structures and proper-
ties, substituted triazoles have been widely used in ma-
terial science, agricultural chemistry and bio-pharma-
ceutical.[1] Particularly, large numbers of 1,2,3-triazoles
have recently been discovered to have remarkable bio-
activity, such as IDO1 inhibitor, antiviral agent, Src ki-
nase inhibitor and HDAC inhibitor (Figure 1, a－d). In
the past few decades, a variety of methods have been
developed for the construction of 1,2,3-triazoles.[2,3] The
common approaches rely on the classical Cu(I)-, Ru(II)-
or Ir-catalyzed azide-alkyne cycloadditions.[4-7] Recently,
organo-catalyzed 1,3-dipolar cycloaddition of organic
azides with α,β-unsaturated acyl azoliums,[8] and con-
densation of N-tosylhydrazones with anilines,[9] have
been developed for the synthesis of 1,2,3-triazoles.
In 2014, we developed an efficient 1,3-dipolar cy-
cloaddition of nitroolefins and inorganic NaN3 for the
synthesis of 4-aryl-NH-1,2,3-triazoles (Scheme 1a).[11]
To suppress the undesired cyclotrimerization of ni-
troolefins, the reaction was conducted under p-TsOH-
mediated acidic conditions. To our knowledge, the reac-
tion was one of the most effective methods for the syn-
thesis of 4-aryl-NH-1,2,3-triazoles to date. However, the
explosive and toxic hydrazoic acid was released inevi-
tably under the acidic conditions.[12] This safety issue of
the reaction prompted us to develop a safe protocol for
the synthesis of NH-1,2,3-triazoles. Since the nitroole-
fins could be easily synthesized by condensation of al-
dehydes and nitroalkanes,[13] we hypothesized that
1,3-dipolar cycloaddition of in situ generated nitroole-
fins and inorganic NaN3 for the synthesis of NH-1,2,3-
triazoles might be achieved under neutral conditions.[14]
In this case, the undesired cyclotrimerization of ni-
troolefins might be inhibited through rapid cycloaddi-
tion of in situ generated nitroolefins and NaN3. There-
fore, in this paper, we described the development of an
one-pot reaction of aldehydes, nitroalkanes, and NaN3
for the safe and step-economic synthesis of 4-aryl-NH-
O
N
N
N
N
N
O
N
NH
Cl
NH
N
antiviral agent, b
IDO1 inhibitor, a
O
OH
NH
O
N
N
N
N
n
N
N
S
n = 3,4
Src kinase inhibitor, b
HDAC inhibitor, d
Figure 1 Selected examples of biologically active 1,2,3-tria-
zoles.
*
E-mail: guanzhh@nwu.edu.cn
Received May 29, 2017; accepted July 4, 2017; published online XXXX, 2017.
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/cjoc. 201700367 or from the author.
Chin. J. Chem. 2017, XX, 1—5
© 2017 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
1

Hui et al.
COMMUNICATION
1,2,3-triazoles (Scheme 1b).
the best reaction media for this transformation (Table 1,
Entries 6－8). Inspired by the pioneer copper(I)-cata-
lyzed cycloaddition reaction for the synthesis of 2-sub-
stituted-1,2,3-triazoles,[15] we envisioned that a buffer
reaction system might prompt this one-pot three-com-
ponent reaction. Therefore, PivOH and HOAc were
tested as the additives (Table 1, Entries 9－10). The
yield of 3a was dramatically improved to 72% in the
presence of 0.5 equivalent of PivOH (Table 1, Entry 9).
Indeed, this safe buffer reaction conditions show great
effectivity for the one-pot three-component reaction,
and 93% yield of 3a was obtained when 0.5 equivalent
of HOAc was used as the additive (Table 1, Entry 10).
Finally, the reaction temperature was also varied, and
100 ℃ was still the best choice (Table 1, Entries 11
and 12).
Scheme 1 Synthesis of 4-aryl-NH-1,2,3-triazoles
(a)
Our previous work:
NO2
N
N
NH
N
p-TsOH
R
NaN3
+
DMF, 60 oC
R
(b)
R1
This work:
N
CHO
NH
one-pot
2
+
R CH2NO2
+
NaN3
R1
NH4OAc/HOAc
R2
safe reaction step-economy mild conditions
Experimental
Table 1 Optimization of reaction conditionsa
General information
N
NH
N
ammonium salt
additive
solvent, 100 oC
Column chromatography was carried out on silica
CHO
1
+
+ NaN3
CH3NO2
gel. H NMR spectra were recorded at 400 MHz in
DMSO-d6 and 13C NMR spectra were recorded at 100
MHz in DMSO-d6. All new products were further
1a
2a
3a
1
characterized by HRMS; copies of their H NMR and
13C NMR spectra are provided in Supporting
Information. Unless otherwise stated, all reagents and
solvents were purchased from commercial suppliers and
used without further purification.
Entry
Ammonium salt
NH4OAc
(NH4)2CO3
NH4HCO3
NH4Cl
Additive Solvent Yieldb/%
1
2
DMF
DMF
DMF
DMF
DMF
DMAC
DMSO
NMP
DMF
DMF
DMF
DMF
54
41
43
48
39
49
47
35
72
93
66
72
3
Typical procedure for the synthesis of 4-aryl-NH-
1,2,3-triazoles: Aldehydes 1 (0.3 mmol), nitroalkanes 2
(0.9 mmol), NaN3 (0.75 mmol), HOAc (0.15 mmol),
NH4OAc (0.3 mmol) and DMF (3 mL) were charged in
a 10 mL round bottom flask. Then, the reaction mixture
was stirred at 100 ℃. When the reaction was completed
(detected by TLC), the mixture was cooled to room
temperature. The reaction was quenched with H2O (10
mL) and extracted with EtOAc (10 mL×3). The com-
bined organic layers were dried over anhydrous Na2SO4
and then evaporated in vacuo. The corresponding tria-
zoles were obtained after purification by flash chroma-
tography on silica gel with hexane/ethyl acetate (V/V＝
5∶1) as the eluent.
4
5
HCOONH4
NH4OAc
NH4OAc
NH4OAc
NH4OAc
NH4OAc
NH4OAc
NH4OAc
6
7
8
9
PivOH
HOAc
HOAc
HOAc
10
11c
12d
a Reaction conditions: benzaldehyde 1a (0.3 mmol), nitromethane
2a (3.0 equiv.), NaN3 (2.5 equiv.), ammonium salt (1.0 equiv.),
and additive (0.5 equiv.) in solvent (3 mL) at 100 ℃ under air.
b Isolated yield. c The reaction was performed at 80 ℃. d The
reaction was performed at 110 ℃.
Results and Discussion
Initially, benzaldehyde 1a, nitromethane 2a and
NaN3 were selected as model substrates to optimize the
reaction conditions. Considering that the condensation
of aldehydes and nitroalkanes was conventionally pro-
ceeded in the presence of NH4OAc in HOAc solvent,[13a]
we began our investigation with NH4OAc in DMF.
Gratifyingly, the desired 4-phenyl-NH-1,2,3-triazole 3a
was obtained in 54% yield at 100 ℃ (Table 1, Entry 1).
Then, various ammonium salts such as (NH4)2CO3,
NH4HCO3, NH4Cl and HCOONH4 were screened (Ta-
ble 1, Entries 2－5). However, no further improvement
was observed. Optimization of different solvents such as
DMAC, DMSO and NMP, suggested that DMF was still
With the optimized reaction conditions in hand, a se-
ries of aldehydes 1 were investigated for extending the
substrate scope (Table 2). This transformation proved to
be a general method for the preparation of 4-aryl-NH-
1,2,3-triazoles. In all cases examined, the para-, meta-
and ortho-substituted aromatic aldehydes were all con-
verted into substituted 1,2,3-triazoles in good to excel-
lent yields. Aryl aldehydes with electron-donating sub-
stituents on aryl rings, such as methyl and methoxyl,
proceeded smoothly and resulted in the desired triazoles
3b－3f in 88%－96% yields. Furthermore, salicylalde-
2
www.cjc.wiley-vch.de
© 2017 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2017, XX, 1—5

One-Pot Synthesis of 4-Aryl-NH-1,2,3-Triazoles
Table 2 Reaction scope of aldehydes 1, nitromethane 2a and
NaN3
hyde and 4-(dimethylamino)benzaldehyde also exhibit-
ed good reactivity and gave the triazoles 3g－3h in 82%
and 70% yields, respectively. To further investigate the
scope of this reaction with regard to other functional
groups, substrates containing halo substituents such as
fluoro, chloro, bromo, and iodo were tested. The corre-
sponding triazoles 3i－3r were afforded in good to high
yields. Aryl aldehydes with strong electron-withdrawing
groups such as trifluoromethyl and nitro, afforded the
triazoles 3s－3u in moderate yields, implying that the
electronic nature of the substrates has slight influence
on the reaction. Furthermore, when 2,4-dichloroben-
zaldehyde and 2,4,6-trimethylbenzaldehyde were em-
ployed as multisubstituted substrates, the reaction re-
acted well to give the corresponding triazoles 3v－3w in
good yields. 2-Naphthylbenzaldehyde participated in the
reaction smoothly and afforded the desired triazole 3x in
79% yield. Heterocyclic substituted aldehydes such as
furyl, thienyl, and indolyl, were well tolerated in the
reaction to give the corresponding triazoles 3y－3aa in
80%－86% yields. In addition, the desired triazole 3ab
was obtained in only 10% yield when cinnamaldehyde
was employed as the vinyl substituted aldehyde. How-
ever, no reaction occurred when aliphatic aldehydes
such as cyclohexanecarbaldehyde and pentanal were
used as the substrates.
a
N
N
NH
N
NH
N
N
N
NH
3a, 93%
3c, 93%
3b, 88%
N
N
N
N
N
N
O
NH
NH
NH
O
N
3d, 92%
3e, 96%
3f, 95%
N
N
N
N
N
N
OH
NH
NH
NH
F
3g, 82%
3i, 87%
3h
, 70%
N
N
N
N
N
N
F
NH
NH
NH
F
Cl
3j, 78%
3k, 68%
3l, 85%
N
N
N
N
N
N
Cl
In an attempt to provide access to a broader range of
triazoles, the reaction with different nitroalkanes was
investigated under the standard conditions (Scheme 2).
Gratifyingly, nitroethane and 1-nitropropane 2b－2c
proceeded smoothly to give the corresponding triazoles
4b－4c in 91%－97% yields. Moreover, ester substi-
tuted NH-1,2,3-triazole 4d could also be synthesized in
36% yield.
NH
NH
NH
Cl
Br
3m, 70%
3n, 75%
3o, 79%
N
N
N
N
N
N
Br
NH
NH
NH
Br
I
3q, 63%
3p, 72%
3r, 61%
Scheme 2 Reaction scope of benzaldehyde 1a, nitroalkanes 2
N
N
N
NH
N
NH
and NaN3
N
N
NH
O2N
F3C
F3C
3s, 58%
3t, 62%
3u, 51%
N
NH
N
N
N
N
N
Cl
NH
NH
Cl
3x, 79%
3v, 68%
3w, 86%
N
N
N
N
N
NH
N
It should be noted that alkyl azides were also toler-
ated in this three-component reaction. Interestingly,
4-phenyl-NH-1,2,3-triazole 3a was obtained in 80%
yield when azidotrimethylsilane (TMSN3) was used as
the substrate (Scheme 3).
NH
NH
HN
S
O
3z, 86%
3aa, 80%
3y, 84%
N
NH
N
N
N
N
N
NH
NH
Scheme 3 Three-component reaction of benzaldehyde 1a, ni-
tromethane 2a and TMSN3
3ad, 0%
3ab, 10%
3ac, 0%
a Reaction condition: 1 (0.3 mmol), nitromethane 2a (3.0 equiv.),
NaN3 (2.5 equiv.), NH4OAc (1.0 equiv.), HOAc (0.5 equiv.),
DMF (3 mL) at 100 ℃, isolated yield.
Chin. J. Chem. 2017, XX, 1—5
© 2017 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.cjc.wiley-vch.de
3

Hui et al.
COMMUNICATION
To demonstrate the synthetic utility of this reaction,
a gram-scale (10 mmol, 1.06 g) reaction was performed
under the standard conditions. Expectedly, the 4-phenyl-
NH-1,2,3-triazole 3a was obtained in 84% yield
(Scheme 4).
Conclusions
In summary, a safe, facile and step-economic three-
component reaction of aldehydes, nitroalkanes and in-
organic NaN3 for the synthesis of 4-aryl-NH-1,2,3-tria-
zoles has been developed in the paper. NH4OAc/HOAc
plays a crucial role in the reaction. The reaction em-
ploys readily available starting materials, tolerates a
wide range of functional groups, thus providing an effi-
cient method for the synthesis of valuable NH-1,2,3-
triazoles in high to excellent yields. Further reaction
scope and applications are underway in our lab.
Scheme 4 Gram scale reaction
N
N
NH
CHO
+
standard conditions
NaN
CH NO
+
3
3
2
3a
(1.22 g, 84%)
1a
2a
(10 mmol, 1.06 g)
Acknowledgement
To further gain insights into the reaction mechanism,
nitroalkene 5a was synthesized to undergo the cycload-
dition reaction with NaN3 under the standard conditions.
As expected, the desired 4-phenyl-NH-1,2,3-triazole 3a
was obtained in 94% yield (Scheme 5). The results fur-
ther confirm the proposed reaction mechanism which is
shown in Scheme 6.[16] Firstly, the nitroolefin 5 was eas-
ily synthesized by condensation of benzaldehyde 1 and
nitroalkane 2. At the same time, the reaction between
ammonium acetate and sodium azide afforded ammo-
nium azide. Then, the nucleophilic addition of ammo-
nium azide to nitroolefin 5 afforded the intermediate 6.
An intramolecular nucleophilic cyclization of interme-
diate 6 gave the intermediate 7. Next, elimination of a
molecule of NH4NO2 generated the intermediate 8. Fi-
nally, isomerization of the intermediate 8 produced the
1,2,3-triazole 4.
This work was supported by the National Natural
Science Foundation of China (Nos. 21622203,
21472147) and the Fund of the Shanxi Province (No.
2016JM2007).
References
[1] (a) Thirumurugan, P.; Matosiuk, D.; Jozwiak, K. Chem. Rev. 2013,
113, 4905; (b) Lau, Y. H.; Rutledge, P. J.; Watkinson, M.; Todd, M.
H. Chem. Soc. Rev. 2011, 40, 2848; (c) Roḧrig, U. F.; Majjigapu, S.
R.; Caldelari, D.; Dilek, N.; Reichenbach, P.; Ascencao, K.; Irving,
M.; Coukos, G.; Vogel, P.; Zoete, V.; Michielin, O. Bioorg. Med.
Chem. Lett. 2016, 26, 4330.
[2] For recent reviews, see: (a) Alonso, F.; Moglie, Y.; Radivoy, G. Acc.
Chem. Res. 2015, 48, 2516; (b) Thomas, J.; Jana, S.; Liekens, S.;
Dehaen, W. Chem. Commun. 2016, 52, 9236; (c) Chen, Z.; Liu, Z.;
Cao, G.; Li, H.; Ren, H. Adv. Synth. Catal. 2017, 359, 202.
[3] Selected examples, see: (a) Jia, F.-C.; Xu, C.; Zhou, Z.-W.; Cai, Q.;
Li, D.-K.; Wu, A.-X. Org. Lett. 2015, 17, 2820; (b) Xie, Y.-Y.; Wang,
Y.-C.; He, Y.; Hu, D.-C.; Wang, H.-S.; Pan, Y.-M. Green Chem. 2017,
19, 656; (c) Cioc, R. C.; Ruijter, E.; Orru, R. V. A. Green Chem.
2014, 16, 2958; (d) Ali, A.; Corrêa, A. G.; Alves, D.; Zuker-
man-Schpector, J.; Westermann, B.; Ferreira, M. A. B.; Paixão, M.
W. Chem. Commun. 2014, 50, 11926; (e) Chen, Z.; Yan, Q.; Liu, Z.;
Xu, Y.; Zhang, Y. Angew. Chem., Int. Ed. 2013, 52, 13324; (f) Roy,
S.; Chatterjee, T.; Islam, S. M. Green Chem. 2013, 15, 2532.
[4] For recent reviews, see: (a) Johansson, J. R.; Beke-Somfai, T.; Said
Stålsmeden, A.; Kann, N. Chem. Rev. 2016, 116, 14726; (b) Wei, F.;
Wang, W.; Ma, Y.; Tung, C.-H.; Xu, Z. Chem. Commun. 2016, 52,
14188; (c) Hein, J. E.; Fokin, V. V. Chem. Soc. Rev. 2010, 39, 1302;
(d) Kappe, C. O.; Van der Eycken, E. Chem. Soc. Rev. 2010, 39,
1280.
Scheme 5 1,3-Dipolar cycloaddition of nitroolefin with NaN3
Scheme 6 Plausible reaction mechanism
[5] Cu-catalyzed azide-alkyne cycloaddition reactions: (a) Zhou, W.;
Zhang, M.; Li, H.; Chen, W. Org. Lett. 2017, 19, 10; (b) Bai, Y.;
Feng, X.; Xing, H.; Xu, Y.; Kim, B. K.; Baig, N.; Zhou, T.; Gewirth,
A. A.; Lu, Y.; Oldfield, E.; Zimmerman, S. C. J. Am. Chem. Soc.
2016, 138, 11077; (c) Rasina, D.; Lombi, A.; Santoro, S.; Ferlin, F.;
Vaccaro, L. Green Chem. 2016, 18, 6380; (d) Zhou, F.; Tan, C.; Tang,
J.; Zhang, Y.-Y.; Gao, W.-M.; Wu, H.-H.; Yu, Y.-H.; Zhou, J. J. Am.
Chem. Soc. 2013, 135, 10994; (e) Zhang, Y.; Li, X.; Li, J.; Chen, J.;
Meng, X.; Zhao, M.; Chen, B. Org. Lett. 2012, 14, 26; (f) Wang, D.;
Li, N.; Zhao, M.; Shi, W.; Ma, C.; Chen, B. Green Chem. 2010, 12,
2120.
[6] Ru-catalyzed azide-alkyne cycloaddition reactions: (a) Das, U. K.;
Jena, R. K.; Bhattacharjee, M. RSC Adv. 2014, 4, 21964; (b) Liu, P.
N.; Siyang, H. X.; Zhang, L.; Tse, S. K. S.; Jia, G. J. Org. Chem.
2012, 77, 5844.
[7] Ir-catalyzed azide-alkyne cycloaddition reactions: (a) Ding, S.; Jia,
G.; Sun, J. Angew. Chem., Int. Ed. 2014, 53, 1877; (b) Rasolofonja-
4
www.cjc.wiley-vch.de
© 2017 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2017, XX, 1—5

One-Pot Synthesis of 4-Aryl-NH-1,2,3-Triazoles
tovo, E.; Theeramunkong, S.; Bouriaud, A.; Kolodych, S.; Chau-
montet, M.; Taran, F. Org. Lett. 2013, 15, 4698.
(c) Wu, L.; Wang, X.; Chen, Y.; Huang, Q.; Lin, Q.; Wu, M. Synlett
2016, 27, 437.
[8] (a) Li, W.; Ajitha, M. J.; Lang, M.; Huang, K.-W.; Wang, J. ACS
Catal. 2017, 7, 2139; (b) Li, W.; Du, Z.; Zhang, K.; Wang, J. Green
Chem. 2015, 17, 781; (c) John, J.; Thomas, J.; Dehaen, W. Chem.
Commun. 2015, 51, 10797; (d) Ramasastry, S. S. V. Angew. Chem.,
Int. Ed. 2014, 53, 14310; (e) Li, W.; Du, Z.; Huang, J.; Jia, Q.;
Zhang, K.; Wang, J. Green Chem. 2014, 16, 3003; (f) Zhao, M.-N.;
Zhang, M.-N.; Ren, Z.-H.; Wang, Y.-Y.; Guan, Z.-H. Sci. Bull. 2017,
62, 493.
[9] (a) Ren, A.; Lu, P.; Wang, Y. Chem. Commun. 2017, 53, 3769; (b)
Bai, H. W.; Cai, Z. J.; Wang, S. Y.; Ji, S. J. Org. Lett. 2015, 17, 2898;
(c) Cai, Z.-J.; Lu, X.-M.; Zi, Y.; Yang, C.; Shen, L.-J.; Li, J.; Wang,
S.-Y.; Ji, S.-J. Org. Lett. 2014, 16, 5108; (d) van Berkel, S. S.;
Brauch, S.; Gabriel, L.; Henze, M.; Stark, S.; Vasilev, D.; Wessjo-
hann, L. A.; Abbas, M.; Westermann, B. Angew. Chem., Int. Ed.
2012, 51, 5343.
[13] (a) Lopchuk, J. M.; Hughes, R. P.; Gribble, G. W. Org. Lett. 2013, 15,
5218; (b) Ishitani, H.; Saito, Y.; Tsubogo, T.; Kobayashi, S. Org. Lett.
2016, 18, 1346; (c) Fioravanti, S.; Pellacani, L.; Tardella, P. A.; Ver-
gari, M. C. Org. Lett. 2008, 10, 1449; (d) Hu, Q.; Liu, Y.; Deng, X.;
Li, Y.; Chen, Y. Adv. Synth. Catal. 2016, 358, 1689; (e) Sengupta, S.;
Duan, H.; Lu, W.; Petersen, J. L.; Shi, X. Org. Lett. 2008, 10, 1493;
(f) Zhang, H.; Dong, D.-Q.; Wang, Z.-L. Synthesis 2016, 48, 131.
[14] (a) Feng, J.; Ablajan, K.; Ma, X.; Li, W.; Obul, M. Chin. J. Org.
Chem. 2016, 36, 222; (b) Roppe, J.; Smith, N. D.; Huang, D.; Teh-
rani, L.; Wang, B.; Anderson, J.; Brodkin, J.; Chung, J.; Jiang, X.;
King, C.; Munoz, B.; Varney, M. A.; Prasit, P.; Cosford, N. D. P. J.
Med. Chem. 2004, 47, 4645; (c) Xing, X.; Fan, K.; Pang, H.; Wu, Y.;
Yang, J.; Shi, W.; Xie, Z.; Hui, Y. Chin. J. Org. Chem. 2016, 36,
1942; (d) Tang, M.; Wu, Y.; Liu, Y.; Cai, M.; Xia, F.; Liu, S.; Hu, W.
Acta Chim. Sinica 2016, 74, 54; (e) Chen, M.; Zhang, W.; Ren, Z.-H.;
Gao, W.-Y.; Wang, Y.-Y.; Guan, Z.-H. Sci. China Chem. 2017, 60,
761.
[10] Thomas, J.; John, J.; Parekh, N.; Dehaen, W. Angew. Chem., Int. Ed.
2014, 53, 10155.
[11] Quan, X.-J.; Ren, Z.-H.; Wang, Y.-Y.; Guan, Z.-H. Org. Lett. 2014,
16, 5728.
[12] (a) Yao, B.; Liu, Y.; Zhao, L.; Wang, D.-X.; Wang, M.-X. J. Org.
Chem. 2014, 79, 11139; (b) Evers, J.; Göbel, M.; Krumm, B.; Martin,
F.; Medvedyev, S.; Oehlinger, G.; Steemann, F. X.; Troyan, I.;
Klapötke, T. M.; Eremets, M. I. J. Am. Chem. Soc. 2011, 133, 12100;
[15] Kalisiak, J.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2008, 10, 3171.
[16] (a) Singh, S.; Samanta, S. Chin. J. Chem. 2015, 33, 1244; (b) Li, Z.;
Yan, N.; Xie, J.; Liu, P.; Zhang, J.; Dai, B. Chin. J. Chem. 2015, 33,
589; (c) Hao, C.; Zhou, C.; Xie, J.; Zhang, J.; Liu, P.; Dai, B. Chin. J.
Chem. 2015, 33, 1317; (d) Chai, H.; Guo, R.; Yin, W.; Cheng, L.;
Liu, R.; Chu, C. ACS Comb. Sci. 2015, 17, 147.
(Zhao, X.)
Chin. J. Chem. 2017, XX, 1—5
© 2017 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.cjc.wiley-vch.de
5