an unprecedented use for glycerol: chemoselective reducing ... · bis(p‐tolyl)sulfide was formed...
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An Unprecedented Use for Glycerol: Chemoselective Reducing
Agent for Sulfoxides
Nuria García, Patricia García‐García, Manuel A. Fernández‐Rodríguez, Daniel García, María R.
Pedrosa, Francisco J. Arnáiz, and Roberto Sanz*
Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Bañuelos
s/n, 09001‐Burgos, Spain
Electronic Supplementary Information
Index
General methods ................................................................................................................................... 2
General procedures for the reduction of sulfoxides ............................................................................. 3
General procedure for the Mo‐catalyzed oxidation of glycerol with bis(p‐tolyl)sulfoxide ................... 4
General procedure for the reduction of sulfoxides using oxidation products from glycerol as
reducing agents ..................................................................................................................................... 4
NMR studies and spectra for the determination of glycerol oxidation products in the process ......... 5
NMR spectra of products obtained after extraction in Table 2 and Schemes 1, 2 and 3 ..................... 13
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General methods: All reactions were assembled under air atmosphere unless otherwise
noted. All reaction temperatures refer to bath temperatures. All common reagents and
solvents were obtained from commercial suppliers and used without any further purification.
Non commercially available sulfoxides were prepared by oxidizing the precursor sulfide with
NaIO4 (1 equiv) or with H2O2 according to established procedures.1 Sulfides precursors of 1‐
(pent‐4‐enylsulfinyl)benzene and 1‐(pent‐4‐ynylsulfinyl)benzene were synthesized from
thiophenol and the corresponding alkyl bromide in the presence of a base. The catalyst,
MoO2Cl2(dmf)2, was prepared as previously reported.2 Solvents were dried by standard
methods. TLC was performed on aluminum‐backed plates coated with silica gel 60 with F254
indicator; the chromatograms were visualized under ultraviolet light and/or by staining with a
Ce/Mo reagent and subsequent heating. NMR spectra were measured on Varian Mercury‐Plus
300 MHz and Varian Inova‐400 MHz spectrometers. GC‐MS were recorded on an Agilent
6890N/5973 Network GC System, equipped with a HP‐5MS column. Products were isolated in
greater than 95% purity, as determined by 1H NMR spectroscopy 3 and capillary gas
chromatography (GC). The microwave heating was performed in a microwave reactor (CEM
Discover S‐Class) with a single‐mode microwave cavity producing continuous irradiation
(Temperature measurements were conducted using an IR sensor located below the microwave
cavity floor, and reaction times refer to the total hold time at the indicated temperature. The
maximum wattage supplied was 300 W).
1 W. L. Xu, Y. Z. Li, Q. S. Zhang and H. S. Zhu, Synthesis, 2004, 227.
2 R. Sanz, J. Escribano, R. Aguado, M. R. Pedrosa, and F. J. Arnáiz, Synthesis, 2004, 16291632.
3 Spectroscopical data of the synthesized sulfides were identical to those previously reported: N. García,
P. García‐García, M. A. Fernández‐Rodríguez, R. Rubio, M. R. Pedrosa, F. J. Arnáiz and R. Sanz, Adv. Synth.
Catal., 2012, 354, 321327.
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General procedures for the reduction of sulfoxides:
Method A: A mixture of glycerol (921 mg, 10 equiv.), sulfoxide (1 mmol) and
MoO2Cl2(dmf)2 (17 mg, 5 mol%) was heated at 170 °C overnight. The reaction mixture was
cooled to room temperature and Et2O (20 mL) and water (20 mL) were added. The layers were
separated and the aqueous layer extracted with Et2O (2 × 20 mL). The combined organic layers
were dried over anhydrous Na2SO4, filtered, and the solvents were removed under reduced
pressure. The corresponding sulfide was obtained in almost pure form without further
purification in the yields reported in Table 2.
Method B: A mixture of glycerol (921 mg, 10 equiv.), sulfoxide (1 mmol) and
MoO2Cl2(dmf)2 (9 mg, 2.5 mol%) was heated at 200 °C for 24 h. The reaction mixture was
cooled to room temperature and Et2O (20 mL) and water (20 mL) were added. The layers were
separated and the aqueous layer extracted with Et2O (2 × 20 mL). The combined organic layers
were dried over anhydrous Na2SO4, filtered, and the solvents were removed under reduced
pressure. The corresponding sulfide was obtained in almost pure form without further
purification in the yields reported in Table 2.
Method C: A mixture of glycerol (111 mg, 1.2 equiv.), sulfoxide (1 mmol) and
MoO2Cl2(dmf)2 (9 mg, 2.5 mol%) in toluene (1 mL) was irradiated in a sealed tube in the
microwave cavity at 230 °C for 5 min. The reaction mixture was cooled to room temperature
and Et2O (20 mL) and water (20 mL) were added. The layers were separated and the aqueous
layer extracted with Et2O (2 × 20 mL). The combined organic layers were dried over anhydrous
Na2SO4, filtered, and the solvents were removed under reduced pressure. The corresponding
sulfide was obtained in almost pure form without further purification in the yields reported in
Table 2.
Recycling study: A mixture of glycerol (92 g, 100 equiv.), bis(p‐tolyl)sulfoxide (2.3 g, 10
mmol) and MoO2Cl2(dmf)2 (90 mg, 2.5 mol%) was heated at 200 °C for 46 h. The reaction
mixture was cooled to 100 °C and extracted with hot toluene (3 × 50 mL). The combined
organic layers were dried over anhydrous Na2SO4, filtered, and the solvents were removed
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under reduced pressure. Bis(p‐tolyl)sulfide was obtained in almost pure form without further
purification in the yields reported in Scheme 2. The glycerolic phase was reused in the next
cycle.
Using crude glycerol: A mixture of crude glycerol (2.36 g, ca. 58% purity, ca. 2 equiv.),
sulfoxide (1 mmol) and MoO2Cl2(dmf)2 (9 mg, 2.5 mol%) was heated at 200 °C for 27 h in an
open flask until complete consumption of the starting material (determined by GC‐MS
analysis). The reaction mixture was cooled to room temperature and Et2O (20 mL) and H2O (20
mL) were added. The layers were separated and the aqueous layer extracted with Et2O (2 × 20
mL). The combined organic layers were dried over anhydrous Na2SO4, filtered, and the solvents
were removed under reduced pressure. The corresponding sulfide was obtained in almost
pure form without further purification in the yields reported in Scheme 3.
General procedure for the Mo‐catalyzed oxidation of glycerol with bis(p‐tolyl)sulfoxide: A
mixture of bis(p‐tolyl)sulfoxide (230 mg, 1 mmol), the appropriate amount of glycerol (18
equiv.), MoO2Cl2(dmf)2 (9 mg, 2.5 mol%) in mesitylene (2 mL) was heated at 200 °C for 9 h. The
reaction mixture was cooled to room temperature and Et2O (20 mL) and water (20 mL) were
added. The layers were separated and the aqueous layer extracted with Et2O (2 × 20 mL). The
combined organic layers were dried over anhydrous Na2SO4, filtered, and the solvents were
removed under reduced pressure. Bis(p‐tolyl)sulfide was formed in the conversions estimated
by 1H NMR (300 MHz) reported in Scheme 4.
General procedure for the reduction of sulfoxides using oxidation products from glycerol as
reducing agents: A mixture of bis(p‐tolyl)sulfoxide (230 mg, 1 mmol), the appropriate amount
of reducing agent (16 equiv.), and MoO2Cl2(dmf)2 (9 mg, 2.5 mol%) in toluene (1 mL) was
irradiated in a sealed tube in the microwave cavity at 180 or 230 °C for 5 min. The reaction
mixture was cooled to room temperature and Et2O (20 mL) and H2O (20 mL) were added. The
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layers were separated and the aqueous layer extracted with Et2O (2 × 20 mL). The combined
organic layers were dried over anhydrous Na2SO4, filtered, and the solvents were removed
under reduced pressure to give bis(p‐tolyl)sulfide in the conversions and yields reported in
Table 3.
NMR studies and spectra for the determination of glycerol oxidation products in the process:
A mixture glycerol (276 mg, 3 mmol), the appropriate amount of DMSO‐d6 (1 to 6 equiv.), and
MoO2Cl2(dmf)2 (917 mg, 2.55.0 mol%) was heated at 170 °C overnight or at 200 °C for 4 h.
After cooling, the crude reaction mixture was homogenized, if necessary, by adding additional
DMSO‐d6 and its 13C NMR was measured. In the spectra reported below of all the experiments
performed we could observe the signals corresponding to the formation of formic acid ( =
167.7) as main product as well as variable amounts of remaining glycerol ( = 73.8 and 64.4).
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MoO2Cl2(dmf)2
(5 mol%)+
170 °C, 17 hOHHO
OH
DMSO-d6
6 1
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MoO2Cl2(dmf)2
(5 mol%)+
170 °C, 17 hOHHO
OH
DMSO-d6
6 1
OHO+
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MoO2Cl2(dmf)2
(2.5 mol%)+
200 °C, 4 hOHHO
OH
DMSO-d6
4 1
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MoO2Cl2(dmf)2
(5 mol%)+
170 °C, 17 hOHHO
OH
DMSO-d6
2 1
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MoO2Cl2(dmf)2
(2.5 mol%)+
200 °C, 4 hOHHO
OH
DMSO-d6
2 1
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MoO2Cl2(dmf)2
(5 mol%)+
170 °C, 17 hOHHO
OH
DMSO-d6
1 1
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MoO2Cl2(dmf)2
(2.5 mol%)+
200 °C, 4 hOHHO
OH
DMSO-d6
1 1
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NMR spectra of products obtained after extraction in Table 2 and Schemes 1, 2 and 3
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Method A
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Method A(25 mmol)
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Method B
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Method C
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Method C0.25 mol% cat.
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Method A
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Method B
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Method C
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Cl Cl
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Cl Cl
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Cl Cl
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Cl Cl
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Cl Cl
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Br
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Br
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Br
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Method B
Br
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Br
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Method C
Br
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Method A
NC
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Method A
NC
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Method B
NC
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Method B
NC
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Method C
NC
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NC
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Method C
CO2Me
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CO2Me
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Method C
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Method C
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Method C
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Method C
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Method A
O2N
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Method B
O2N
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Method C
O2N
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Method C
O2N
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81
00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0.5f1 (ppm)
3.32
2.07
2.00
2.36
7.12
7.13
7.15
7.26
7.27
7.29
7.29
Electronic Supplementary Material (ESI) for Green ChemistryThis journal is © The Royal Society of Chemistry 2013
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84
00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0.5f1 (ppm)
3.04
2.00
1.62
2.36
7.12
7.12
7.12
7.12
7.15
7.15
7.26
7.27
7.29
Electronic Supplementary Material (ESI) for Green ChemistryThis journal is © The Royal Society of Chemistry 2013
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85
00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0.5f1 (ppm)
14.2
9
6.72
8.81
2.00
2.37
2.39
7.13
7.13
7.16
7.27
7.27
7.29
7.29
7.31
7.57
7.60
Electronic Supplementary Material (ESI) for Green ChemistryThis journal is © The Royal Society of Chemistry 2013