Rongalite promoted highly regioselective synthesis of β- hydroxytellurides

Article abstract of DOI:10.3184/174751911X13049538828959

Ditellurides undergo facile cleavage on treatment with rongalite (sodium hydroxymethanesulfinate) to generate tellurium anions in situ, which undergo ring opening of epoxides in high regioselective manner. A simple, cost-effective method has been develope

Full text of DOI:10.3184/174751911X13049538828959

288 RESEARCH PAPER
MAY, 288–290
JOURNAL OF CHEMICAL RESEARCH 2011
Rongalite promoted highly regioselective synthesis of
β-hydroxytellurides
Dongsheng Sui, Feifei Wu, Qing Xu* and Xiaochun Yu*
College of Chemistry and Materials Engineering, Wenzhou Universtity, Wenzhou 325035, P. R. China
Ditellurides undergo facile cleavage on treatment with rongalite (sodium hydroxymethanesulfinate) to generate tel-
lurium anions in situ, which undergo ring opening of epoxides in high regioselective manner. A simple, cost-effective
method has been developed to prepare β-hydroxytellurides with good yields.
Keywords: β-hydroxytellurides, rongalite, expoxide, ditellurides
Tellurium compounds contain an extremely rich chemistry and
are widely applied in many areas, such as metallurgy, indus-
trial chemicals and electronic conductors.1–4 Organotellurium
compounds have become attractive synthetic targets because
of their chemo-, regio-, and stereoselective reactions, in the
presence of a wide variety of functional groups, thus avoiding
the need for protecting group chemistry. They have useful bio-
logical activities.5–7 β-Hydroxytellurides are important inter-
mediates comparable to β-hydroxy selenides8–12 and β-hydroxy
sulfides,13–17 but fewer methods have been developed to syn-
thesise organotellurium compounds. The classical synthesis
of β-hydroxytellurides involves the ring opening of an epoxide
by a telluride in the presence of NaBH4/EtOH system18 or
from ditellurides with a NaBH4/EtOH system,19 a AlH(Bu-i)2/
THF system,20 a MeOH-NaClO4-(Pt) system21 or a LiAlH4/
THF system.22 Other methods to obtain β-hydroxytellurides
involving some of these reagents have their own advantages.
However, these procedures possess one or more disadvantages
such as expensive metallic reagents,20 water sensitivity,20,22
or unusual instruments21 which might limit the scale of an
experiment.Thus, thereisstillaneedtofindnewmethodologies
for the synthesis of β-hydroxytellurides.
Based on the fact that rongalite (sodium formaldehyde sulf-
oxylate, NaHSO2·CH2O·2H2O as an inexpensive reagent) pro-
motes the formation of thiolate anions or selenolate anions23,
we now report that tellurium anions generated from ditellu-
rides by the action of rongalite, will open epoxide rings and
produce β-hydroxytellurides efficiently and regioselectively.
Initial studies were carried out using 7-oxabicyclo[4.1.0]
heptane (1a) with 1,2-diphenylditelluride as a model substrate
to explore the reaction conditions (Scheme 1). The results were
shown in Table 1.
Table 1 Effects of rongalite, solvent, and reaction temperature
on the ring opening of epoxide with diphenylditelluride
Entry
Rongalite Solvent
/equiv.
Time/min
T/°C Yield/%a
1
2
3
3
3
3
4
5
6
5
5
5
5
5
DMF
DMF
DMF
DMF
DMF
DMF
DMF
H2O
5
5
r. t.
70
0
0
3
5
100
130
130
130
130
130
130
130
130
130
0
4
5
50
5
10
10
5
82
6
87
7
88
8
5
NR
Trace
Trace
0
9
THF
5
10
11
12
CH3CN
Toluene
DMF
5
5
5
87b
aBased on isolated product.
bWithout K2CO3.
the yield was not affected when the reaction was carried out
without the addition of K2CO3 (Table 1, entries 12). This was
different from the ring opening reaction of epoxides with
diphenyldisulfides or diphenyldiselenides which did not take
place in absence of base.24,25 We consider that the high tem-
perature promoted the formation of tellurium anions directly
without the help of a base.
To establish the generality of the methodology, a variety of
epoxides were treated with the diphenylditellurides under the
optimised condition to afford β-hydroxytellurides. The results
are listed in Table 2.
As shown in Table 2, the reaction of epoxides 1a–g with
diphenylditellurides mediated by rongalite resulted in the
formation of the corresponding β-hydroxytellurides 2a–m in
good yield. It should be noted that the ring-opening of epox-
ides produced only one product 2 in our procedure, as the
result of the epoxides undergoing facile ring opening in the
usual manner at the less hindered carbon centre. The reaction
showed excellent regioselectivity. However, if the oxirane had
two bulky groups on 2, 3 position separately (Table 2, entries
14, 15), the reaction did not proceed smoothly even if the reac-
tion time was prolonged to 24 hours. This can be explained on
the basis of two factors. One is that the bulky groups prevented
the attack of nucleophile, the other is that the telluride anion is
itself a bulky group, compared to the other chalcogen anion
such as the sulfide, selenide anion.
Compared with the ring opening of epoxides with disulfides
or diselenides mediated by the rongalite which occurs at room
temperature,24,25 it was found that the reaction did not occur
satisfactorily until the reaction temperature was raised to
130 °C (Table 1, entries 1–3). The amount of rongalite affected
the yield dramatically (Table 1, entries 4–6). When 4 equiv. of
rongalite was added to the reaction system and the reaction
time was shortened to 10 min, 82% yield of the product was
obtained. Among the solvents that were screened, (acetonitrile,
water, THF, Toluene and DMF) (Table 1, entries 7–11), DMF
afforded a useful result. It should be especially noted that
In conclusion, an efficient and simple method for the syn-
thesis of β-hydroxytellurides with high regioselectivity by ring
opening of epoxides with diphenylditellurides promoted by
inexpensive rongalite in the absence of metal and base has
been developed. Compared to the previous reports, our method
has advantages such as high regioselectivity, high yields,
simple operations and no requirement for expensive metallic
reagents.
Scheme 1
* Correspondent. E-mail: chinaxiaochunyu@126.com

JOURNAL OF CHEMICAL RESEARCH 2011 289
158.2, 138.4, 129.4, 129.3, 127.8, 121.2, 114.5, 111.4, 71.5, 70.1,
13.6. HRMS: Calcd for C15H16O2Te: 358.0213. Found: 358.0212.
1-(4-Fluorophenyltellanyl)-3-phenoxypropan-2-ol (2d):Yellow oil;
1H NMR (300 MHz, CDCl3): δ (ppm) 7.72 (t, J = 6.6 Hz, 2H), 7.26 (t,
J =7.5 Hz, 2H), 6.95 (t, J = 7.5 Hz, 1H), 6.93–6.82 (m, 4H), 4.15–4.13
(m, 1H), 4.04–3.94 (m, 2H), 3.14 (d, J = 6.1 Hz, 2H), 2.77 (br, 1H,
OH). 13C NMR (125 MHz, CDCl3): δ (ppm) 163.0 (d, JC-F = 246.7 Hz),
158.2, 140.9 (d, JC-F = 7.6 Hz), 129.5, 121.2, 116.7 (d, JC-F = 20.8 Hz)
114.5, 105.0, 71.4, 70.0, 14.2; IR(liquid film): 3415 cm−1, 2851 cm−1,
2159 cm−1, 1585 cm−1, 1364 cm−1, 1079 cm−1, 822 cm−1, 690 cm−1; MS
(EI, 70eV) m/z (%): 376 (38), 372 (22), 225 (27), 133 (54), 107 (100)
77 (84), 51 (18). HRMS: Calcd for C15H15FO2Te: 376.0118. Found:
376.0119.
Table 2 Ring-opening of epoxides with diphenylditellurides in
the presence of rongalite
Entry
Epoxide
R
Product Yield/%a
R1
R2
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
-(CH2)4-
-(CH2)4-
C6H5OCH2
C6H5OCH2
n-C6H13
n-C6H13
ClCH2
ClCH2
C6H5
C6H5
C6H5
p-(F) C6H4
C6H5
p-(F) C6H4
C6H5
p-(F) C6H4
C6H5
p-(F) C6H4
C6H5
p-(F) C6H4
C6H5
p-(F) C6H4
C6H5
2a
2b
2c
2d
2e
2f
2g
2h
2i
2j
2k
2l
2m
2n
2o
90
86
85
87
80
80
85
84
72
50
88
65
83
–
1
1-(Phenyltellanyl)octan-2-ol 2e: H NMR (500 MHz, CDCl3): δ
(ppm) 7.75–7.73 (m, 2H), 7.30–7.26 (m, 1H), 7.21–7.18 (m, 2H),
3.73–3.68 (m, 1H), 3.16 (dd, J = 4.0, J = 12.0 Hz, 1H), 2.98 (dd, J =
8.0, 12.0 Hz, 1H), 2.24 (br, 1H, OH), 1.54–1.53 (m, 2H), 1.28–1.25
(m, 7H), 0.88–0.85 (m, 3H). 13C NMR (125 MHz, CDCl3): δ (ppm)
138.4, 129.2, 127.8, 111.3, 71.1, 37.9, 31.7, 29.2, 25.9, 22.5, 20.3,
14.0; HRMS: Calcd for C14H22OTe: 336.0733. Found: 336.0734.
1-(4-Fluorophenyltellanyl)octan-2-ol (2f): Yellow oil; 1H NMR
(300 MHz, CDCl3): δ (ppm) 7.75–7.70 (m, 2H), 6.90 (t, J = 8.7 Hz,
2H), 3.69 (m, 1H), 3.12 (dd, J = 3.9, 9.3 Hz, 1H), 2.96 (dd, J = 7.2,
12.0 Hz, 1H), 2.28 (d, J = 4.0 Hz, OH), 1.82–1.52 (m, 2H),1.49–1.25
(m, 8H), 0.87 (t, J = 6.9 Hz, 3H). 13C NMR (125 MHz, CDCl3):
δ (ppm) 162.9 (d, JC-F = 246.2 Hz), 140.9 (d, JC-F = 7.5 Hz), 116.6 (d,
JC-F = 20.0 Hz), 104.9 (d, JC-F = 7.5 Hz), 71.1, 37.9, 31.7, 29.1, 25.8,
22.5, 20.7, 14.0; IR (liquid film): 3428 cm−1, 2927 cm−1, 2855 cm−1,
2026 cm−1, 1702 cm−1, 1580 cm−1, 1484 cm−1, 1085 cm−1; MS (EI,
70eV) m/z (%): 354 (18), 240 (21), 109 (14), 95 (34), 69 (100), 55
(46). HRMS: Calcd for C14H21FOTe: 354.0639. Found:354.0637.
H
H
H
H
H
H
H
H
C6H5
C6H5CO
C2H5OCO
C6H5
C6H5
C6H5
–
a Based on an isolated product. The regioisomer 3 was not de-
tected by 1HNMR.
1
1-Chloro-3-(phenyltellanyl)propan-2-ol (2g): Yellow oil; H NMR
(300 MHz, CDCl3): δ (ppm) 7.75 (d, J = 7.5Hz,2H 2H), 7.32–7.18 (m,
3H), 4.00–3.96 (m, 1H), 3.69–3.60 (m, 2H), 3.09 (d, J = 6.4 Hz, 2H),
2.71 (br, 1H, OH). 13C NMR (125 MHz, CDCl3): δ (ppm) 138.5,
129.3, 128.0, 111.0, 71.3, 49.4, 14.0; IR(liquid film): 3735 cm−1, 3650
cm−1, 3009 cm−1, 2860 cm−1, 2158 cm−1, 1716 cm−1, 1363 cm−1, 1223
cm−1; MS (EI, 70eV) m/z (%): 302 ([M+2]+, 5), 300 (M+, 22), 224
(19), 205 (16), 130 (8), 91 (34), 77 (100), 51 (46). HRMS: Calcd for
C9H11ClOTe, 299.9561. Found:299.9563.
Experimental
Chemicals and solvents were either purchased or purified by standard
techniques. IR spectra were recorded on a NICOLET IS10-Infrared
Spectrophotometer. NMR spectroscopy was performed on both a
Bruker-300 spectrometer operating at 300 MHz (1H NMR), 500 MHz
(1H NMR) and 125 MHz (13C NMR). TMS (tetramethylsilane) was
used as an internal standard and CDCl3 was used as the solvent. Mass
spectrometric analysis was performed on GC–MS analysis (SHI-
MADZU GCMS-QP2010). HRMS (EI) analysis was performed by
the analytical centre at the Shanghai Institute of Organic Chemistry,
Chinese Academy of Sciences.
1-Chloro-3-(4-fluorophenyltellanyl)propan-2-ol (2h): Yellow oil;
1H NMR (300 MHz, CDCl3): δ (ppm) 7.77–7.72 (m, 2H), 6.92 (t, J =
8.8 Hz, 2H), 3.99–3.97 (m, 1H), 3.67–3.64 (m, 2H), 3.07 (d, J=6.3 Hz,
2H), 2.68 (d, J = 4.0 Hz, 1H, OH). 13C NMR (125 MHz, CDCl3):
δ (ppm) 163.1 (d, JC-F = 247.1 Hz), 141.2 (d, JC-F = 7.6 Hz), 116.8 (d,
JC-F = 20.8 Hz) 104.6 (d, J = 3.6Hz), 71.2, 49.4, 14.5; IR(liquid film):
3447 cm−1, 2931 cm−1, 1578 cm−1, 1484 cm−1, 1388 cm−1, 1228 cm−1,
1160 cm−1, 1062 cm−1; MS (EI, 70eV) m/z (%): 320 ([M+2]+, 12), 318
(M+, 47), 242 (38), 225 (39), 95 (100), 75 (44), 57 (31). HRMS: Calcd
for C9H10ClFOTe: 317.9466. Found: 317.9467.
Preparation of 2a–m; general procedure
A mixture of epoxides (0.5 mmol), diphenylditellurides (0.2 mmol),
and rongalite (1.0 mmol) in DMF (2.0 mL) was stirred at 130 °C for
10 min under air. The reaction mixture was washed with ethyl acetate.
After adding enough silica gel to the mixture, the combined washings
was evaporated under vacuum directly. The residue was purified by
flash column chromatography to afford the desired product 2.
Trans-2-(phenyltellanyl)cyclohexanol (2a):26 1H NMR (300 MHz,
CDCl3): δ (ppm) 7.83–7.80 (m, 2H), 7.37–7.32 (m, 1H), 7.24–7.20
(m, 2H), 3.40 (m, 1H), 3.08 (ddd, J = 3.9, 12.6, 16.2 Hz 1H), 2.73 (br,
1H, OH), 2.30 (d, J = 12.6 Hz, 1H), 2.16–2.12 (m, 1H), 1.78–1.76 (m,
1H), 1.56–1.48 (m, 2H), 1.32–1.19 (m, 3H). 13C NMR (125 MHz,
CDCl3): δ (ppm) 141.0, 129.2, 128.3, 109.6, 73.7, 39.8, 35.2, 34.3,
27.9, 24.8.
1-Phenyl-2-(phenyltellanyl)ethanol (2i):27 1H NMR (300 MHz,
CDCl3) : δ (ppm) 7.70 (d, J = 6.9 Hz 2H), 7.32–7.15 (m, 8H), 4.86 (m,
1H), 3.28–3.25 (m, 2H), 2.76 (br, 1H, OH); 13C NMR (125 MHz,
CDCl3) δ: 143.5, 138.4, 129.2, 128.5, 127.8, 127.7, 125.6, 111.5, 73.6,
20.7.
1
1-(4-Fluorophenyl)-2-(phenyltellanyl)ethanol (2j): Yellow oil; H
NMR (300 MHz, CDCl3) δ: 7.68–7.63 (m, 2H), 7.32–7.25 (m, 5H),
6.88 (t, J = 8.7 Hz 2H), 4.88–4.83 (m, 1H), 3.28–3.23 (m, 2H), 2.65
(br, 1H, OH); 13C NMR (125 MHz, CDCl3) δ: 162.9 (d, JC-F = 246.2
Hz), 143.4, 140.9 (d, JC-F = 7.5 Hz), 128.5, 127.9, 125.6, 116.6 (d,
JC-F = 20.0 Hz) 105.0, 73.7, 21.1; IR(liquid film): 3443 cm−1, 2928
cm−1, 2856 cm−1, 2159 cm−1, 1578 cm−1, 1483 cm−1, 1453 cm−1, 821
cm−1; MS (EI, 70eV) m/z (%): 346 (23), 240 (30), 225 (21), 104 (71),
103 (100), 77 (96), 51 (42). HRMS: Calcd for C14H13FOTe: 346.0013.
Found: 346.0011.
1
Trans-2-(4-fluorophenyltellanyl)cyclohexanol (2b): Yellow oil; H
NMR (300 MHz, CDCl3): δ (ppm) 7.81–7.76 (m, 2H), 6.92 (t, J = 8.7
Hz, 2 H), 3.42–3.34 (m, 1H), 3.05 (ddd, J = 3.9, 14.1, 15.9 Hz, 1H),
2.64 (br s, 1H, OH), 2.26 (d, J = 12.0 Hz, 1H), 2.17–2.12 (m, 1H),
1.79–1.77 (m, 1H), 1.52–1.46 (m, 2H), 1.33–1.19 (m, 3H). 13C NMR
(125 MHz, CDCl3): δ (ppm) 163.2 (d, JC-F = 247.4 Hz), 143.2 (d, JC-F
= 7.6 Hz), 116.5 (d, JC-F = 20.7 Hz) 103.2 (d, J = 3.7 Hz), 73.60, 39.4,
35.0, 34.4, 27.7, 24.7; IR(liquid film): 3448 cm−1, 2928 cm−1, 2854
cm−1, 1578 cm−1, 1483 cm−1, 1228 cm−1, 1219 cm−1, 1107 cm−1; MS
(EI, 70eV) m/z (%): 324 (9), 226 (9), 95 (26), 81 (100), 55 (22).
HRMS: Calcd for C12H15FOTe: 324.0169. Found: 324.0168.
1-(Phenyltellanyl)dec-9-en-2-ol (2k): Yellow oil;.1H NMR (300
MHz, CDCl3): δ (ppm) 7.76 (d, J = 7.1 Hz 2H), 7.31–7.17 (m, 3H),
5.87–5.73 (m, 1H), 5.02–4.91 (m, 2H), 3.70 (m, 1H), 3.16 (dd, J = 3.9,
12.3 Hz,1H), 2.97 (dd, J = 8.1, 12.3 Hz, 1H), 2.20 (br, 1H, OH), 2.02
(q, J = 6.9 Hz, 2H), 1.55–1.50 (m, 2H),1.35–1.26 (m, 8H). 13C NMR
(125 MHz CDCl3): δ (ppm) 139.0, 138.4, 129.2, 127.7, 114.2, 111.3,
71.1, 37.9, 33.7, 29.3, 28.9, 28.8, 25.9, 20.3; IR(liquid film):
3428 cm−1, 2925 cm−1, 2854 cm−1, 2159 cm−1, 1702 cm−1, 1575 cm−1,
1434 cm−1, 1113 cm−1; MS (EI, 70eV) m/z (%): 362 (15), 207 (26),
205 (18), 81 (47), 77 (65), 55 (100). HRMS: Calcd for C16H24OTe:
362.0889. Found: 362.0888.
1-Phenoxy-3-(phenyltellanyl)propan-2-ol (2c): 1H NMR (300
MHz,CDCl3) δ: 7.74 (dd, J = 1.2, 8.1Hz, 2H), 7.28–7.14 (m, 5H), 6.95
(t, J = 7.3 Hz, 1H), 6.84 (dd, J = 0.9, 8.7 Hz, 2H), 4.16 (m, 1H),4.03
(dd, J = 3.9, 9.3 Hz, 1H), 3.97 (dd, J = 6.3, 9.3 Hz, 1H), 3.18 (d, J =
6.3 Hz, 2H), 2.76 (br, 1H, OH). 13C NMR (125 MHz, CDCl3): δ (ppm)

290 JOURNAL OF CHEMICAL RESEARCH 2011
1-(4-Fluorophenyltellanyl)dec-9-en-2-ol (2l): Yellow oil; 1H NMR
(300 MHz, CDCl3): δ (ppm) 7.75–7.71 (m, 2H), 6.90 (t, J = 8.7 Hz,
2H), 5.87–5.73 (m, 1H), 5.01–4.82 (m, 2H), 3.69 (m, 1H), 3.12 (dd,
J = 3.9, 12.0 Hz, 1H), 2.95 (dd, J = 7.8, 12.0 Hz, 1H),2.16 (br, 1H,
OH), 2.02 (q, J = 6.9Hz, 2H), 1.54–1.27 (m, 10H). 13C NMR (125
MHz, CDCl3): δ (ppm) 163.2 (d, JC-F = 245.0 Hz), 141.1 (d, JC-F = 7.6
Hz), 139.0, 116.7(d, JC-F = 20.8 Hz), 114.2, 104.8 (d, J = 3.6 Hz), 71.1,
37.9, 33.7, 29.7, 29.3, 29.0, 28.8, 25.9, 20.8; IR(liquid film): 3566
cm−1, 2925 cm−1, 2854 cm−1,1715 cm−1, 1575 cm−1, 1484 cm−1, 1363
cm−1, 1223 cm−1; MS (EI, 70eV) m/z (%): 380 (26), 240 (9), 225 (28),
95 (90), 55 (100). HRMS: Calcd for C16H23FOTe: 380.0795. Found:
380.0796.
3
4
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NMR (300 MHz, CDCl3): δ (ppm) 7.75–7.72 (m, 2H), 7.27–7.16 (m,
3H), 5.87–5.81 (m, 1H), 5.28–5.16 (m, 2H), 3.96–3.94 (m, 3H), 3.53
(dd, J = 3.6, 9.3 Hz, 1H), 3.44 (dd, J = 6.3, 9.3 Hz, 1H), 3.07 (d, J =
6.3 Hz, 2H), 2.83 (d, J = 2.4 Hz, 1H, OH). 13C NMR (125 MHz,
CDCl3): δ (ppm) 138.2, 134.2, 129.1, 127.6, 117.3, 111.7, 73.9, 72.1,
70.3, 13.7; IR (liquid film): 3419 cm−1, 2920 cm−1, 2855 cm−1,
1709 cm−1, 1575 cm−1, 1433 cm−1, 1364 cm−1, 1018 cm−1; MS
(EI, 70eV) m/z (%): 322 (24), 207 (39), 117 (29), 91 (36), 77 (100),
51 (32). HRMS: Calcd for C12H16O2Te: 322.0213. Found: 322.0214.
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We thank the Natural Science Foundation of Zhejiang
Province (Y4100579), and the Postgraduate Department of
Wenzhou University (3160603601010935) for the financial
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Received 28 February 2011; accepted 18 April 2011
Paper 1100598 doi: 10.3184/174751911X13049538828959
Published online: 1 June 2011
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