Electrochemical Synthesis of 1,2,4-Thiadiazoles through Intermolecular Dehydrogenative S-N Coupling

Article abstract of DOI:10.1002/adsc.201901290

An electrochemical intermolecular dehydrogenative coupling reaction of isothiocyanates with 2-aminopyridines/amidines was developed. Using n-Bu₄NI as the catalyst and electrolyte, 1,2,4-thiadiazoles and pyrido-fused 1,2,4-thiadiazoles were readily accessed with good to excellent efficiency under the undivided electrolysis conditions. This electrochemical approach obviates the use of external oxidants and transition-metal catalysts. (Figure presented.).

Full text of DOI:10.1002/adsc.201901290

Title: Electrochemical Synthesis of 1,2,4-Thiadiazoles through
Intermolecular Dehydrogenative S-N Coupling
Authors: Jiang-Sheng Li, Xin-Yun Xie, Pan-Pan Yang, Si Jiang, Li Tao,
Zhi-Wei Li, Cui-Hong Lu, and Wei-Dong Liu
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To be cited as: Adv. Synth. Catal. 10.1002/adsc.201901290
Link to VoR: http://dx.doi.org/10.1002/adsc.201901290

Advanced Synthesis & Catalysis
10.1002/adsc.201901290
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DOI: 10.1002/adsc.201901290
Electrochemical Synthesis of 1,2,4-Thiadiazoles through
Intermolecular Dehydrogenative S-N Coupling
a
a
a
a
b
a
Jiang-Sheng Li, * Xin-Yun Xie, Pan-Pan Yang, Si Jiang, Li Tao, Zhi-Wei Li, Cui-
a
c
Hong Lu and Wei-Dong Liu
a
Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, School of Chemistry
and Food Engineering, Changsha University of Science & Technology, Changsha, 410114, China
Fax: (+86)-73185258733; Phone: (+86)-73185258733; e-mail: jsli@csust.edu.cn
b
c
State Grid Hunan Electric Power Company Limited Research Institute, Changsha, 410004, China
National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha
4
10007, China.
Received: ((will be filled in by the editorial staff))
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/adsc.201######.((Please
delete if not appropriate))
Abstract:
An
electrochemical
intermolecular the reaction voltage and current renders it possible for
dehydrogenative coupling reaction of isothiocyanates with sulfur compounds to be exclusively converted to
2
[
9]
-aminopyridines/amidines was developed. Using n-Bu4NI desired oxidative products through mild oxidation.
as the catalyst and electrolyte, 1,2,4-thiadiazoles and Lei group has ever reported the electrochemical cross
pyrido-fused 1,2,4-thiadiazoles were readily accessed with dehydrogenative coupling of aryl isothiocyanates with
good to excellent efficiency under the undivided
secondary aliphatic amines for synthesis of
electrolysis conditions. This electrochemical approach
benzothiazoles via C-S bond formation (Scheme
obviates the use of external oxidants and transition-metal
catalysts.
[10]
1
). In continuation of our interests in heterocycles
[11]
construction, herein, we present an electrochemical
dehydrogenative [3+2] annulation of isothiocyanates
with 2-aminopyridines or amidines, without the
involvement of external metal reagents and chemical
oxidants, to furnish 1,2,4-thiadiazoles and
heterocyclic fused analogues via the creation of S-N
bond (Scheme 1).
Keywords: Electrosynthesis; Dehydrogenative coupling;
S-N formation; 1,2,4-Thiadiazoles; Isothiocyanates
The cross dehydrogenative coupling (CDC)
constitutes a fundamental strategy for chemical bond
construction in organic synthesis.[ Among these
CDC processes, C-based coupling reactions have
1,2,4-Thiadiazole scaffolds exist as prominent
structural units in a considerable number of bioactive
1]
[12]
molecules including pharmaceuticals, the assembly
[9b, 13]
of which has attracted much attention.
Our
[1a-g, 2]
received the most extensive interest.
In contrast,
efforts have been devoted to establishing the synthetic
methodologies for heterocycle construction and
modification. Thus we chose the annulation of phenyl
isothiocyanate (1a) with 2-aminopyridine (2a) as the
model reaction to seek optimum reaction conditions
coupling transformations between heteroatoms (e.g. P,
[1h, 3]
S, N) have been addressed comparatively less.
The S-N moiety exists in a series of bioactive
compounds, such as sulfonamides, thiadiazoles. The
recent decade has witnessed great progress made on
[3d, 4]
oxidative S-N bond formation.
However, the use of electrochemical dehydrogenative S-N coupling for
of stoichiometric oxidants or transition metals is
usually required. The main obstacle of
dehydrogenative S-N coupling lies in the liability to
over-oxidation of sulfur-containing components in the
presence of external oxidants as hydrogen acceptors.
Thus, it is much desirable to seek mild oxidative
conditions to efficiently deliver S-N bond without
concurrent over-oxidation side products.
Electrochemical synthesis has proven to be an
emerging powerful and environmentally friendly tool
[5]
in academic and industrial fields, not only for the
Scheme
formation from isothiocyanates.
1
Electrochemical oxidative N-S/C bond
[6]
functional group transformations, cross coupling
reactions,[
5b, 7]
but also for the heterocycles
construction.[ The ease and simplicity to finely tune
8]
1
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Advanced Synthesis & Catalysis
10.1002/adsc.201901290
access to 1,2,4-thiadiazole and its fused heterocycles. whereas the use of graphite rod as anode or Zn and Sn
Electrolysis was performed in a three-necked flask plates as cathode deteriorated the coupling efficiency
charged with Pt plates as anode and cathode whilst (Table 1, entries 9-12). Slightly increasing the dose of
stirring. Initially, the reaction was conducted in a substrate 1a could help improve the product yield
mixture of MeCN and MeOH (1:1) at a constant (Table 1, entries 1 & 13). Therefore, the optimized
current (5 mA) at room temperature using 0.25 electrolysis conditions were established as follows:
equivalent of n-Bu
product 3aa was isolated in 86% yield (Table 1, entry constant current (5 mA) under air at room temperature
). Other supporting electrolytes such as NH I, KI, for 6 h.
NaI, n-Bu NBr and n-Bu NBF were tested, and it Under the standard electrolysis conditions, the
4
NI. Delightedly, the desired 0.2 equivalent of n-Bu
4
NI in MeCN:MeOH (1:1) in a
2
4
4
4
4
was found that the iodide salts could trigger the investigation of substrate scope was next conducted.
electrochemical annulation in moderate to good yields, All the isothiocyanates and aza-heterocycles
while the bromide or tetrafluoroborate salts are containing a marked amidine moiety tested reacted
ineffective (Table 1, entries 3 vs 4). Notably, smoothly to furnish their desired products in good to
decreasing the loading amount of n-Bu
equivalent gave the same yield (Table 1, entry 1), but aryl isothiocyanates (–Me, –OMe, –F, –Cl, –CF
the further shrinkage dramatically lowered the –NO ) could be well tolerated in this electrolysis
reaction yields (Table S1, entries 9-11). Thus, n- (3ab-3gb). As for substrates 1, electron-donating
4
NI to 0.2 excellent yields (Table 2). Different substituents of
3
, and
2
Bu NI (0.2 equivalent) as both supporting electrolyte groups (3bb-3cb) favored the reaction efficiency over
4
and mediator was the best choice for this electrolysis.
The current ranging from 2 to 6 mA delivered yields Table 2. Substrate scopes for the synthesis of fused
ab
of 70-84% (Table 1, entry 5), but increasing the thiadiazoles.
current to 10 mA or no electricity gave trace or no
product (Table S1, entries 16, 18). The use of other
solvent systems, such as MeCN, MeOH or their
mixture with water (1:1) seriously diminished the
reaction efficacy, and slightly adjusting the ratio of
MeCN and MeOH exerted a limited impact (Table 1,
entries 6-8). Furthermore, the electrodes were
examined. Interestingly, graphite felt or Reticulated
Vitreous Carbon (RVC) as anode afforded
comparable yields,
Table 1 Optimization of the electrolysis conditions a
aReaction conditions: Pt plate electrodes (1 cm × 1 cm),
aReaction conditions: 1a (0.2 mmol), 2a (0.2 mmol), n-
undivided cell, constant current = 5 mA (janode = 6.25 mA·
-
2
4
cm ), 1 (0.24 mmol), 2 (0.2 mmol), n-Bu NI (20 mol%),
4
Bu NI (0.2 equiv), MeCN: MeOH (1:1, 3 mL), Pt plates (1
solvent (3 mL), under air atmosphere at room temperature
cm × 1 cm) as anode and cathode, constant current = 5 mA
b
c
for 6 h (5.6 F/mol). Isolated yield. Reticulated Vitreous
Carbon (RVC) as anode (100 PPI, 1 cm × 1 cm × 1.2 cm).
-
2
(janode = 6.25 mA · cm ), undivided cell, under air
b
atmosphere at room temperature for 6 h. Yields are for
c
isolated products. 1a (1.2 equiv).
2
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Advanced Synthesis & Catalysis
10.1002/adsc.201901290
electron-withdrawing ones (3db-3gb). The use of
Scheme
2
Amidines as coupling partners with
ortho-,
meta-
or
para-methylated
phenyl isothiocyanates for synthesis of 1,2,4-thiadiazoles
isothiocyanates gave comparable yields of
corresponding products (3bb, 3hb, 3ib), suggesting
that the substituent steric properties of substrates 1
had no significant effects on the electrolysis. Besides,
aliphatic isothiocyanates were found to be effective
partners with yields of more than 80% (3lb-3mb).
Noteworthy, this electrochemical transformation was
compatible with an allyl group (3mb). Likewise, this
electrochemical coupling reaction was applicable to
various 2-aminopyridines, with groups like –Me, –
OMe, and –Br. Notably, the reaction was greatly
governed by electron properties of groups on the
pyridine core (3ac vs 3af), but not by steric effects
(
3bb, 3ac, and 3ad). Besides, 2-aminoquinoline was
used instead to produce its desired thiadiazole in 71%
yield (3ag).
Next, we further examined unsubstituted
benzimidine hydrochloride (4) and N-phenyl
benzimidine (6) instead of 2-aminopyridines under
the standard electrolysis conditions (Scheme 2). It
turned out that both of them performed well with
phenyl or 4-toly isothiocyanates to provide annulated
products 5a, 5b, 7a and 7b with up to 91% yields. It
should be pointed out that in the case of substrate 4,
one equivalent of additional base triethylamine was
required to liberate free benzimidine.
Scheme 3 Controlled experiments.
yield. The HRMS analysis of the crude reaction
To gain an insight into this electrolysis, we carried
mixture involving TEMPO showed the presence of
+
out the following controlled experiments (Scheme 3). [M+H] 58.1533 and 293.1869, which likely
When the thiourea 8, readily available from the corresponds to the reduced TEMPO molecule
reaction of 1a with 2a, was subjected to the standard generated in the cathode, and the nucleophilic adduct
electrolysis conditions, no desired product 3aa was
detected. This excluded the possibility of undergoing
a thiourea intermediate. The reaction of 1a with 2b
under iodine (1 equiv) successfully delivered product
9
of this TEMPO anion with 1a, respectively. The
competitive formation of 9 hindered the occurrence of
the desired electrocatalytic coupling reaction. Thus,
the radical process may not be involved in our
electrochemical coupling reaction.
3
ab in 72%, suggesting iodine may be the real
catalyst for this transformation. Further, TEMPO and
,1-diphenylethene as radical trappers were added
Considering that iodine could promote this
dehyrogenative coupling without no electricity, we
recorded the cyclic voltammetry (CV) curves, as
1
respectively in this electrochemical coupling. shown in Figure 1, to identify the role of n-Bu NI.
4
Interestingly, the use of TEMPO nearly stopped the Within the scanning window (< 1.5 V), isothiocyanate
reaction, while the addition of 1,1-diphenylethene 1a displayed no recognizable oxidation peaks at the
absence of the iodide salt (Figure S1, curve c), while
hardly affected the electrolysis, giving 3ab in 89%
2
-aminopyridine (2a) has marked oxidation signal at
ca. 1.35 V (Figure S2, curve c). The curve b of n-
Bu NI showed two oxidation peaks (the obvious at
.72 V), corresponding to the oxidation of I to I
then to I (Figure 1). The addition of n-Bu NI caused
the decrease in the oxidation potential of 2a by about
11 mV (Figure S2, curve d), thereby indicating n-
Bu NI can promote the oxidation of 2a likely through
4
-
-
0
3
and
2
4
1
4
the interference of in-situ generated iodine. The CV
behaviours of this iodide catalysed electrolysis are
very similar to those of the cobalt catalysed
[14]
electrosynthesis.
On the base of the experimental results above, we
proposed a tentative mechanism for this n-Bu NI-
mediated electrochemical coupling reaction (Scheme
). Initially, an iodide anion undergoes electro-
4
4
oxidation in a platinum anode, generating an iodine
molecule, I
2
. Then 2-aminopyridine (2a) tautomerizes
3
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Advanced Synthesis & Catalysis
10.1002/adsc.201901290
Typical Procedure for the Electrosynthesis of the
Cyclization Products.
to generate an imine form I, and reacts with iodine to
give N-iodopyridin-2-amine (II), which resembles the
[
15]
The amidines or 2-amino azaheterocycles (0.2 mmol, 1.0
reaction of 2-methylquinolines with iodine.
The
4
equiv)，isothiocyanates (0.24 mmol, 1.2 equiv)，n-Bu NI
(
0.04 mmol, 0.2 equiv) were placed in a 10 mL three-
necked round-bottomed flask. The flask was equipped with
platinum plate (1 cm × 1 cm) anode and a platinum plate (1
cm × 1 cm) cathode. MeOH (1.5 mL) and MeCN (1.5 mL)
were added. The electrolysis was carried out at room
temperature using a constant current of 5 mA until
complete consumption of the substrate (monitored by TLC,
about 6 h). The reaction mixture was concentrated and the
residue was chromatographed through silica gel eluting
with ethyl acetate/petroleum ether to give the products.
Acknowledgements
We would thank the Financial support from National Key R&D
Program of China (No. 2017YFB0307200), Changsha Municipal
Science and Technology Project (kq1801053), Young Teachers
Development Project of CSUST (2019QJCZ039), Hunan
Provincial Natural Science Foundation of China (2017JJ2275).
Figure 1. Cyclic voltammograms of reactants and their
mixtures in 0.1 M n-Bu NPF /CH CN and CH OH (1:1,
v/v) using a glassy carbon disk working electrode (diameter,
mm), Pt disk and Ag/AgCl (saturated KCl) as counter
4
6
3
3
3
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COMMUNICATION
Electrochemical Synthesis of 1,2,4-Thiadiazoles
through Intermolecular Dehydrogenative S-N
Coupling
Adv. Synth. Catal. 2019, Volume, Page – Page
a
a
a
Jiang-Sheng Li, * Xin-Yun Xie, Pan-Pan Yang, Si
a
b
a
a
Jiang, Li Tao, Zhi-Wei Li, Cui-Hong Lu and
Wei-Dong Liuc
6
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