Diorganyl tellurides as substrates in Sonogashira coupling reactions under mild conditions

Article abstract of DOI:10.1080/00397911.2019.1692224

A new method of Sonogashira coupling reactions between diorganyl tellurides and terminal alkynes is reported. The coupling reactions are performed using Pd(dppf)Cl₂ as a catalyst, CuI as a co-catalyst in the presence of K₂CO₃ in DMSO. The reactions are carried out at room temperature and completed within 2 h when phenyl acetylene is used as a terminal alkyne. For aliphatic terminal alkynes, such as 1-hexyne and 1-octyne, an elevated temperature and longer reaction time are needed for the completion of the reactions. This process results in good yields of Sonogashira coupling products which is applicable for diaryl, divinyl and dialkynyl tellurides but not applicable for dialkyl tellurides.

Full text of DOI:10.1080/00397911.2019.1692224

Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic
Chemistry
ISSN: 0039-7911 (Print) 1532-2432 (Online) Journal homepage: https://www.tandfonline.com/loi/lsyc20
Diorganyl tellurides as substrates in Sonogashira
coupling reactions under mild conditions
Shaozhong Zhang, Chandra Ailneni, Osamah Al-Mohammed Baqer, Mahati
Lolla, Bala Bharathi Mannava, Parvinlal Siraswal, Changchi Yen & Jin Jin
To cite this article: Shaozhong Zhang, Chandra Ailneni, Osamah Al-Mohammed Baqer, Mahati
Lolla, Bala Bharathi Mannava, Parvinlal Siraswal, Changchi Yen & Jin Jin (2019): Diorganyl
tellurides as substrates in Sonogashira coupling reactions under mild conditions, Synthetic
Communications, DOI: 10.1080/00397911.2019.1692224
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SYNTHETIC COMMUNICATIONSV
https://doi.org/10.1080/00397911.2019.1692224
Diorganyl tellurides as substrates in Sonogashira coupling
reactions under mild conditions
Shaozhong Zhang, Chandra Ailneni, Osamah Al-Mohammed Baqer, Mahati Lolla,
Bala Bharathi Mannava, Parvinlal Siraswal, Changchi Yen, and Jin Jin
Department of Chemistry, Western Illinois University, Macomb, IL, USA
ABSTRACT
ARTICLE HISTORY
Received 10 September 2019
A new method of Sonogashira coupling reactions between diorganyl
tellurides and terminal alkynes is reported. The coupling reactions
are performed using Pd(dppf)Cl2 as a catalyst, CuI as a co-catalyst in
the presence of K2CO3 in DMSO. The reactions are carried out at
room temperature and completed within 2 h when phenyl acetylene
is used as a terminal alkyne. For aliphatic terminal alkynes, such as
1-hexyne and 1-octyne, an elevated temperature and longer reaction
time are needed for the completion of the reactions. This process
results in good yields of Sonogashira coupling products which is
applicable for diaryl, divinyl and dialkynyl tellurides but not applic-
able for dialkyl tellurides.
KEYWORDS
Symmetrical diorganyl
telluride; Sonogarshira
coupling; terminal alkynes;
palladium catalyst
GRAPHICAL ABSTRACT
P
d(dpp
f)C
l , C
uI
2
R
R'
RTeR
R'
K
2CO3
,
DMS
O,
N2
Introduction
The coupling of terminal alkynes with aryl/vinyl halides catalyzed by palladium and
other transition metals, termed as Sonogashira coupling reaction, is one of the most
powerful methods for constructing C(sp2)-C(sp) bonds.[1] Sonogashira reactions have
found wide applications in the synthesis of natural products,[2] biologically active mole-
cules,[3] heterocycles,[4] conjugated polymers,[5] molecular electronics,[6] dyes[7]
and sensors.[8]
The large volume of tellurium atom promotes the easy polarization of C-Te bond,
therefore it exhibits a high reactivity and lability. The use of organotellurium com-
pounds in organic synthesis have been increased since 1980s.[9] Applications of organo-
tellurium compounds in organic synthesis can be divided into different types of
functional groups interconversions and carbon-carbon bond forming reactions.[9] A car-
bon–tellurium bond has been transformed into a carbon–halogen bond in several types
of organotellurium compounds.[10] Organotellurium reagents have also found their
applications in the fields of oxidation and reduction reactions.[11] More recently,
CONTACT Jin Jin
j-jin@wiu.edu
Department of Chemistry, Western Illinois University, Macomb, IL, 61455, USA.
Supplemental data for this article is available online at on the publisher’s website.
ß 2019 Taylor & Francis Group, LLC

2
S. ZHANG ET AL.
organotellurium compounds have been successfully used as alternatives to halogens as
electrophilic partners in some Pd-catalyzed cross-coupling reactions, such as Heck,[12]
Negishi,[13] and Stille reactions.[14]
In this article, we reported that unsaturated symmetrical diorganyl tellurides are
viable alternatives as electrophilic sources in Sonogashira cross-coupling reactions. The
main advantages of using diorganyl tellurides as substrates are the simple preparation
and the fact that the oxidative addition of organotellurides on palladium is faster than
organohalides because carbon-tellurium bond is more labile than carbon-halogen bond
and most Sonogashira reactions herein reported occur at room temperature.
Results and discussion
It has been reported that alkyl aryl tellurides were used as coupling partners in Pd-
catalyzed Sonogashria reactions assisted by microwave at 150 ꢀC.[15] In these reactions,
only the aryl groups in the alkyl aryl tellurides are involved in the Sonogashira products
and the alky groups become waste, which results in the poor atom economy. Atom
economy is one of the most widely used metrics to measure the “greenness” of a syn-
thesis.[16] We recently reported a simple method to prepare symmetrical diaryl tellurides
in a catalyst-free condition using Te0 as the chalcogen source in the presence of
KOH.[17] We wonder whether the symmetrical diaryl tellurides can act as a new sort of
the Sonogashira coupling agents in the presence of Pd- and Cu-catalysts. If so, the atom
economy will be greatly improved.
Therefore, we took bis(p-tolyl)telluride, 1a and phenyl acetylene, 2a as the model sub-
strates to investigate the Sonogashira cross-coupling reaction between them (Table 1).
Initially we applied the similar conditions as described in the literature[15] for the
Table 1. Pd/Cu-catalyzed cross-coupling of 1a and 2a.a
Entry
Catalyst
PdCl2/CuI
Pd(OAc)2/CuI
Base
Et3N
Et3N
Et3N
Et3N
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
Solvent
DMSO
Temperature (ꢀC)
Yield (%)b
1
2
3
4
5
6
7
8
120
120
120
trace
trace
20
34
75
75
85
0
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
CH3OH
H2O
DMF
CH3CN
THF
Dioxane
DMSO
DMSO
Pd(PPh3)2Cl2/CuI
Pd(dppf)Cl2/CuI
Pd(dppf)Cl2/CuI
Pd(dppf)Cl2/CuI
Pd(dppf)Cl2/CuI
Pd(dppf)Cl2/CuI
Pd(dppf)Cl2/CuI
Pd(dppf)Cl2/CuI
Pd(dppf)Cl2/CuI
Pd(dppf)Cl2/CuI
Pd(dppf)Cl2/CuI
Pd(dppf)Cl2
120
120
MWc, 150
25
25
25
25
25
25
25
9
0
10
11
12
13
14
15
80
15
10
35
0
25
Pd(PPh3)2Cl2/CuI
MWc, 150
20
aReaction conditions: a mixture of 1a (1 equiv.), 2a (2.5 equiv.), Pd catalyst (10 mol%), CuI (1.2 equiv.), base (2 equiv.)
and solvent (2 mL) was reacted under N2 atomosphere in a sealed tube for 2 h.
bIsolated yield.
cThe reaction was conducted in a microwave synthesizer.

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SYNTHETIC COMMUNICATIONSV
3
coupling of alkyl aryl tellurides with alkynes (Table 1, entry 12), however, the desired
coupling product was only obtained in 20% yield. Then we screened a variety of condi-
tions such as catalysts, bases, solvents and reaction temperatures, as listed in Table 1.
Among the four palladium catalysts (PdCl2, Pd(OAc)2, Pd(PPh3)2Cl2, and
Pd(dppf)Cl2) screened, we found Pd(dppf)Cl2 was the optimal catalyst for the
Sonogashira coupling reaction (Table 1, entry 4). When the base was switched from
Et3N to K2CO3, the yield was observed to be greatly increased to 75% (Table 1, entry
5). We also applied the microwave irradiation on the reaction but didn’t observe the
improvement of the yield (Table 1, entry 6). However, when the temperature was
reduced down to 25 ꢀC, the yield was improved to 85%, probably due to the formation
of less by products at lower temperature (Table 1, entry 7). Among the several solvents
screened, both DMSO and DMF were found to be the proper solvent for the reaction,
with DMSO giving a better yield (Table 1, entry 7 and 10). The absence of CuI as a co-
catalyst resulted in no reaction (Table 1, entry 14), suggesting that both Pd and Cu cata-
lysts were essential for the high efficiency of the transformation. Therefore, the optimal
conditions for the Sonogashira coupling of diaryl tellurides involved the use of 10 mol%
of Pd(dppf)Cl2 and 1.2 equiv. of CuI as the catalysts, K2CO3 as the base, DMSO as the
solvent at room temperature for 2 h.
Next, a series of the symmetrical diaryl tellurides (1a–1l) were prepared in high yields
using the approach mentioned above.[17] Subsequently, under the conditions of entry 7,
Table 1, the Sonogashira cross-coupling reactions were performed on these diaryl tellur-
ides and phenylacetylene, 2a (Table 2). The reactions proceeded nicely at room tem-
perature with electron-withdrawing and electron-donating substituents at ortho, meta or
para position in the aryl architecture.
Then we extended our Sonogashira coupling reactions to aliphatic terminal alkynes
(Table 3) such as 1-hexyne, 2b, 1-octyne, 2c and 3-methoxymethoxy-1-propyne, 2d by
using the reaction conditions mentioned above. In doing this, we took bis(p-tolyl)tellur-
ide, 1a to couple with the aliphatic alkynes. We observed that the products were formed
in low yields at room temperature but the good results were obtained when the reaction
temperature was raised to 100 ꢀC and the time was extended to 12 h.
Next, we tried to explore whether the Sonogashria coupling approach would apply to
other diorganyl tellurides such as bis(vinyl), bis(alkynyl) and dialkyl tellurides.
Therefore, (Z,Z)-bis(phenylethenyl)telluride 1m, bis(phenylethynyl)telluride 1n, and
dibenzyl telluride 1o were prepared according to the literature methods.[18–20] The
Sonogashra coupling reactions were carried out with phenylacetylene thereafter. As
expected, the Sonogashira coupling reaction proceeded nicely for 1m and 1n at room
temperature to give the corresponding coupling products (Z)-enyne 3r and diyne 3s in
high yields, as shown in Table 4. Herein (Z)-enyne 3r was formed stereoselectively from
(Z,Z)-bis(phenylethenyl)telluride 1m. However, no Sonogashira coupling product was
detected for 1o with phenyl acetylene, which means this method is not applicable for
dialkyl tellurides.
Finally a plausible mechanism for the Sonogashira coupling of diorganyl tellurides
with terminal alkynes is shown in Figure 1, which is similar to Sonogashria couplings of
organohalides. By contrast, the reaction begins with oxidative addition of RTeR (instead
of organohalide) to Pd(0) complex to form Pd (II) complex, followed by

4
S. ZHANG ET AL.
Table 2. Sonogashira coupling of various diaryl tellurides and phenylacetylene, 2aa.
Pd(dppf)Cl2 (10 mol%),
CuI (1.2 equiv.)
+
ArTeAr
CH
Ar
2 PhC
2a
K2CO3 (2 equiv.)
DMSO, rt, 2 h
1
3
Yieldb (%)
85
Diaryl tellurides (ArTeAr)
Te
Entry
1
Sonogashira product
1a
Te
3a
3b
88
75
2
3
1b
Te
1c
3c
3d
Te
4
5
82
Cl
1d
Te
1e
Cl
Cl
89
64
H3CO
H3CO
OCH3
3e
3f
Te
6
1f
H3CO
H3CO
Te
OCH3
65
78
7
8
1g
3g
3h
Te
F
F
F
1h
Te
F3CO
65
63
9
F3CO
OCF3
1i
3i
3j
Te
10
1j
Te
H2N
75
81
11
12
H2N
NH2
3k
1k
NH2
NH2
NH2
Te
1l
3l
aReaction conditions: a mixture of 1 (1 equiv.), 2 (2.5 equiv.), Pd(dppf)Cl2 (10 mol%), CuI (1.2 equiv.), K2CO3 (2 equiv.)
and DMSO (2 mL) was reacted under N2 atomosphere in a sealed tube for 2 h.
bIsolated yield.

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SYNTHETIC COMMUNICATIONSV
5
Table 3. Sonogashira coupling of diaryl telluride ArTeAr, 1 with aliphatic term in a lalkynesa.
Pd(dppf)Cl2, CuI
+
ArTeAr
R
R
K2CO3, DMSO
100 oC, 12 h
3
1
2
Yield (%)b
ArTeAr
Entry
1
Aliphatic alkyne
Sonogashra product
1a
(CH2)3CH3
2b
(CH2)3CH3
90
82
3m
3n
2
1b
(CH2)5CH3
2c
(CH2)5CH3
(CH2)3CH3
57
3
4
1b
1b
2b
3o
CH2OCH2OCH3
CH2OCH2OCH3
CH2OCH2OCH3
67
72
2d
3p
3q
5
1d
CH2OCH2OCH3
Cl
2d
aReaction conditions: a mixture of 1a (1 equiv.), 2 (2.5 equiv.), Pd (dppf)Cl2 (10 mol%), CuI (1.2 equiv.), K2CO3 (2 equiv.)
and DMSO (2 mL) was reacted under N2 atomosphere in a sealed tube at 100 ꢀC for 12 h.
bIsolated yield.
Table 4. Sonogashira coupling of other diorganyl telluridesa.
aReaction conditions: a mixture of 1 (1 equiv.), 2a (2.5 equiv.), Pd(dppf)Cl2 (10 mol%), CuI (1.2 equiv.), K2CO3 (2 equiv.)
and DMSO (2 mL) was reacted under N2 atomosphere in a sealed tube for 2 h.
bIsolated yield.
cThe reaction was carried out at both rt and 100 ꢀC.
transmetallation step with organocopper reagent, which is generated by the reaction
between terminal alkyne and copper catalyst. In this transmetallation step the akynyl
anion formed reacts with palladium to replace telluride anion on Pd(II) complex to gen-
erate palladium complex with alkynyl anion. Then the final step is reductive elimin-
ation, which gives coupled product and regenerates the Pd catalyst.

6
S. ZHANG ET AL.
Figure 1. Proposed mechanism for the Sonogashria reaction between diorganyl telluride and ter-
minal alkyne.
Conclusion
In summary, we demonstrated a palladium catalyzed Sonogashira coupling using diaryl
tellurides as substrates under mild reaction conditions and applied to synthesize differ-
ent coupling products. The new method for Sonogashira reactions will lead to a more
benign alternative to the various fields in the synthesis of alkynyl arene-containing mol-
ecules. This method is also applicable for divinyl and dialkynyl tellurides but not applic-
able for dialkyl tellurides.
Experimental
Starting materials and solvents were obtained from Sigma Aldrich or Acros Organic
1
and were used without further purification. H NMR and 13C NMR spectra were meas-
ured (CDCl3 solution) with a JOEL eclipse spectrometer at 400 and 100 MHz, respect-
ively with tetramethylsilane as internal standard. Chromatography columns were
prepared from Merck silica-gel powder. Symmetrical diaryl tellurides,[17] (Z,Z)-bis(phe-
nylethenyl)telluride,[18] bis(phenylethynyl)telluride[19] and dibenzyl telluride[20] were
prepared according to the literature procedure. The compounds reported herein are all
1
known compounds and were identified by H NMR and 13C NMR which were in
accordance with literature data.
General procedure for the sonogashira coupling reactions between diorganyl
tellurides RTeR and phenyl acetylene
P
d(d
pp
f)C
l2
R
R
Te R
C
uI
, K
C
O
, D
MS
O
2
3
r
.t.
/ 2
h
1
2a
3
A mixture of diorganyl telluride RTeR (1 mmol), phenyl acetylene, 2a (0.26 g,
2.5 mmol), Pd(dppf)Cl2 (0.07 g, 0.1 mmol), K2CO3 (0.41 g, 3 mmol) and CuI (0.23 g,
1.2 mmol) in DMSO (3 mL) was stirred at room temperature under N2 for 2 h. The pro-
gress of the reaction was monitored by TLC. After the completion of reaction, the dark

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SYNTHETIC COMMUNICATIONSV
7
precipitate formed was filtered off. The reaction mixture was diluted with CH2Cl2
(20 mL) and the organic layer was washed with water (4 Â 10 mL), dried over anhyd.
Na2SO4, and concentrated under vacuum. The crude product was purified by silica col-
umn chromatography.
General procedure for the sonogashira coupling reactions between diaryl telluride
and aliphatic alkynes
Pd(dppf)Cl2, CuI
ArTeAr
+
R
R
K2CO3, DMSO
3
1
2
100 °C, 12 h
A mixture of diaryl telluride ArTeAr (1 mmol), aliphatic alkynes (1-hexyne, 2b, 1-
octyne, 2c or 3-methoxymethoxy-1-propyne, 2d) (2.5 mmol), Pd(dppf)Cl2 (0.07 g,
0.1 mmol), K2CO3 (0.41 g, 3 mmol) and CuI (0.23 g, 1.2 mmol) in DMSO (3 mL) was
stirred at 100 ꢀC under N2 for 12 h. The progress of the reaction was monitored by
TLC. After the completion of reaction, the dark precipitate formed was filtered off. The
reaction mixture was diluted with CH2Cl2 (20 mL) and the organic layer was washed
with water (4 Â 10 mL), dried over anhyd. Na2SO4, and concentrated under vacuum.
The crude product was purified by silica column chromatography.
Funding
The authors are grateful to NSF MRI award (Acquisition of a 400-MHz NMR Spectrometer to
Support Faculty-Student Research and Training at WIU and Partner Institutions), College of Arts
and Science at WIU for financial support.
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