A general method of Suzuki-Miyaura cross-coupling of 4- and 5-halo-1,2,3-triazoles in water

Article abstract of DOI:10.1039/c7ob02091k

A general method of the synthesis of 1,4,5-trisubstituted-1,2,3-triazoles by Suzuki-Miyaura cross-coupling from 4- and 5-halo-1,2,3-triazoles is reported. The reaction is mediated by an expanded-ring N-heterocyclic carbene palladium complex in water. The

Full text of DOI:10.1039/c7ob02091k

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General method of Suzuki-Miyaura cross-coupling of 4- and 5-
halo-1,2,3-triazoles in water
Pavel S. Gribanov,ab Gleb A. Chesnokov,b Maxim A. Topchiy,ab Andrey F. Asachenkoab and Mikhail
S. Nechaev*ab
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
www.rsc.org/
General method of synthesis of 1,4,5-trisubstituted-1,2,3-triazoles reaction of low-reactive 1,2,3-triazole, harsh conditions were
by Suzuki-Miyaura cross-coupling from 4- and 5-halo-1,2,3- used: 140 °C, 20h using conventional or microwave heating.
triazoles is reported. The reaction is mediated by expanded-ring Xu et al. proposed a modular method of synthesis of 1,4,5-
N-heterocyclic carbene palladium complex in water. The trisubstituted 1,2,3-triazoles from accessible reagents using
developed reaction protocol meets the requirements of “green Cu/Pd transmetallation relay catalyst. This method enables to
chemistry”. Cross-coupling of 4- and 5-chlorotriazoles is reported obtain triazoles bearing three different substituents relatively
for the first time.
easy in one reaction step.12 However, this method has several
disadvantages: 50% excess of organic azide, 50% excess of aryl
halide and from 2 to 10 mol% of palladium precatalyst
Pd2(dba)3, taking into accounts it’s high molecular weight, the
mass of the catalyst is comparable to the mass of organic
substrates. Moreover, one equivalent of copper(I) salt (CuCl),
up to 20 mol% of phosphine ligand, and hazardous teratogenic
DMF solvent are used. Thus, this procedure is far from atom
economy and dangerous for the environment.
1,2,3-triazoles is
a very important class of heterocyclic
compounds widely used as fragments in biologically active
molecules and drugs1 due to broad spectrum of biological
activity, such as antitumor, antiviral and antiparasitic.2 These
heterocycles have found numerous applications in polymer
science,3 as ligands in homogeneous catalysis,4 directing
groups in transition metal catalyzed C-H activations,5 and in
organic synthesis.6 The main approach for synthesis of this
class of heterocycles is a copper catalyzed azide alkyne
cycloaddition.7 This approach is extensively used in
biochemistry and material science.3a, 8
One of the mostly used approaches for the formation of C-C
bonds is palladium-catalyzed cross-coupling reactions that
became a golden standard in organic chemistry and metal
mediated catalysis.13 Among others, Suzuki-Miyaura cross-
coupling is the most preferable. Due to the growing tendency
to avoid hazardous substances in synthesis,14 many variations
of Suzuki-Miyaura methodology using “green” solvents, were
developed.15 Water as solvent is especially attractive since it is
nontoxic, non-flammable, inexpensive, and can be easily
separated from organic products.
The key intermediate in copper(I)-catalyzed alkyne-azide
cycloaddition (CuAAC) reaction that governs high reaction rate
and selectivity is the copper(I) acetylide formed from the
copper catalyst and a terminal alkyne.9 Due to this, CuAAC is
mainly applied in cycloaddition of terminal alkynes. Internal
alkynes are several orders less reactive and there are
difficulties in regio-controlled preparation of fully substituted
1,2,3-triazoles. To date, formation of 1,4,5-trisubstituted 1,2,3-
triazoles via CuAAC remains problematic.10
Recently, 4- and 5-halo-1,2,3-triazoles became more
synthetically accessible.16 Arguably, functionalization of such
substrates via Suzuki-Miyaura cross-coupling might became a
convenient tool for preparation of 1,4,5-trisubstituted 1,2,3-
triazoles. However, there are less than 20 reports in the
literature devoted to cross-coupling of bromo- and iodo-1,2,3-
triazoles (9 references for bromides,17 and 10 for iodides)10b,
17b-d, 18 Most of the reported protocols suffer from a number of
disadvantages: in all cases high loadings of palladium catalysts
(from 4 up to even 20 mol%) are used; utilization of “non-
green” solvents such as DMF, THF, 1,4-dioxane, acetonitrile; in
some cases, harsh reaction conditions should be applied
(intensive microwave heating). Finally, most of the methods
give moderate yields and the scope of substrates is narrow.
1,4,5-Trisubstituted 1,2,3-triazoles can be obtained via CuAAC
reaction followed by transition metal catalyzed C-H
activation/arylation.11 In 2008, the Ackermann group reported
a copper-catalyzed, one-pot two-step coupling reaction of an
alkyne, azide, and an aryl iodide.11c However, to conduct the
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Thus, it can be stated that there is no general approach for triazoles bearing aromatic (3a
Journal Name
-
3h), as well as benzylic (3q-3v)
Suzuki-Miyaura cross-coupling of bromo- and iodo-1,2,3- substituents at the nitrogen atom (Table 1). We then tested a
triazoles to date. Importantly, there are no reports on Suzuki- variety of boronic acids for coupling: donor substituted
Miyaura cross-coupling of chloro-1,2,3-triazoles.
The development of the convenient general approach for substituted (4-fluorophenyl-, 3f
synthesis of 1,4,5-trisubstituted 1,2,3-triazoles is a challenging acetylphenyl-, 3h), sterically hindered (1-naphthyl-, 3d
(phenyl-, 3b
,
3q, para-, 3a
,
3r and ortho-tolyl, 3c
3u; 3-nitrophenyl-, 3l; 4-
3t;
, 3s), acceptor
,
,
task. Thus, we performed a systematic study of the Suzuki- mesityl-, 3g) aryl- and heteroaryl boronic acids (3-thienyl-, 3e
Miyaura reactions of 4- and 5-halo-1,2,3-triazoles with special 3v) can be suitable substrates.
emphasis on coupling of low-reactive challenging chloro-1,2,3-
,
Table 1 Suzuki-Miyaura cross-coupling of 4-halotriazoles in water[a]
triazoles. Where possible, aryl chlorides are employed as the
least expensive of the aryl halides. 19
Previously, our group reported on the development of the
reaction protocol for Suzuki-Miyaura cross-coupling in
water.15k It is of high interest to develop analogous synthetic
procedure for coupling of 4- and 5-halo-1,2,3-triazoles with
arylboronic acids. We used 4-bromo-5-methyl-1,2,3-triazole
(
1a) and 4-methylphenylboronic acid (2a) as a test system for
optimization of reaction conditions.
Scheme 1 Optimization of reaction conditions [a]
a
Reaction conditions: 4-bromo-5-methyl-1-phenyl-1H-1,2,3-triazole (0.5 mmol),
ArB(OH)2 (1.2 eq., 0.6 mmol), (THP-Dipp)Pd(cinn)Cl (0.005 mmol), KOH (1.7 eq.,
b
0.85 mmol), Bu4NBr (0.05 mmol), H2O (0.8 ml), Δ, 8h. NaHCO3 as a base (3.06
eq.). c KOH as a base (1.7 eq.).
Catalytic tests were performed in distilled water as solvent.
NaHCO3 was used as a base, and Bu4NBr as a phase transfer
agent. We tested (THP-Dipp)Pd(cinn)Cl (THP-Dipp = 1,3-bis(2,6-
diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene)
15l, 20
complex bearing expanded-ring carbene15k,
and bulky
Dipp groups as precatalyst.15k Reaction mixtures were refluxed
in air for 8h. The product was isolated using flash-
chromatography to give 82% yield. Upon substitution of 3 eq.
of NaHCO3 with 1.7 eq. of KOH the yield raised up to 97%
(Scheme 1).
iPr
a
Reaction conditions: 4-halo-1,2,3-triazole (0.5 mmol), ArB(OH)2 (1.2 eq., 0.6
mmol), (THP-Dipp)Pd(cinn)Cl (0.005 mmol), KOH (1.7 eq., 0.85 mmol), Bu4NBr
(0.05 mmol), H2O (0.8 ml), Δ, 8h. b NaHCO3 as a base (3.06 eq.)
iPr
N
Ph
Pd
N
Cl
iPr
5-Bromo-1,2,3-triazoles can be efficiently coupled under the
developed conditions (Table 2). Thus, 5-aryl-1,2,3-triazoles,
such as N-benzyl (5a) and N-phenylethyl (5e, 5f) 1,2,3-triazoles
iPr
were obtained in virtually quantitative yields. It is worth
mentioning that 5a can be obtained in virtually quantitative
yield even in presence of a mild base, NaHCO3. Importantly,
the melting temperature of the starting N-substituted 5-
bromo-1,2,3-triazole influence the yield of the reaction. Thus,
5d and 5g were obtained in 20% and 67% yields, respectively.
Most probably, this is due to incomplete melting of the
substrate at 100 °С, leading to incomplete homogeneity of the
(THP-Dipp)Pd(cinn)Cl
In order to determine the substrate scope of Suzuki-Miyaura
cross-coupling of a variety of 4- and 5-bromotriazoles we
further applied the developed conditions to obtain 1,4,5-
trisubstituted 1,2,3-triazoles (Tables 1 and 2). Target 1,4,5-
tisubstituted 1,2,3-triazoles were obtained in yields varying
from good to virtually quantitative from 4-bromo-1,2,3-
2 | J. Name., 2012, 00, 1-3
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reaction mixture. In these two cases, significant amounts of Thus, we developed a versatile, robust, highly active catalytic
starting materials were recovered.
system for coupling of bromo- and chloro-1,2,3-triazoles.
Arylboronic acids bearing donor, acceptor as well as sterically
bulky substituents can be efficiently used as coupling partners.
To our knowledge, this work is the first systematic study of the
Suzuki-Miyaura cross-coupling of 4- and 5-bromo-1,2,3-
triazoles as well as the first report on the Suzuki-Miyaura
cross-coupling of 4- and 5-chloro-1,2,3-triazoles.
Table 2 Suzuki-Miyaura cross-coupling of 5-halotriazoles in water[a]
The reported study was supported by the Russian Science
Foundation (RSF) grant number 17-13-01076.
Authors express their gratitude to Iuliia V. Karsakova and
Alexander Yu. Smirnov for preparation of samples of 4-chloro-
1-phenyl-5-propyl-1H-1,2,3-triazole
(
1b),
4-chloro-1,5-
diphenyl-1H-1,2,3-triazole (1c), 1-benzyl-4-iodo-5-methyl-1H-
1,2,3-triazole (1e).
Notes and references
1
2
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Reaction conditions: 5-halo-1,2,3-triazole (0.5 mmol), ArB(OH)2 (1.2 eq., 0.6
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,
,
,
,
,
,
,
,
,
,
,
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the Suzuki-Miyaura cross-coupling of 4- and 5-halo-1,2,3-
triazoles in water as a solvent. The reaction is mediated by
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several prominent features: a) the reaction takes place in
water with no addition of organic solvents; b) the reaction is
carried out under air, no degasation of water is needed; c)
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