A Convenient and Efficient Rhenium-Catalyzed Hydrosilylation of Ketones
COMMUNICATIONS
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ACHTUNGTRENNUNG
known procedures. Except for the rhenium compounds, all
the chemicals were purchased from Aldrich Chemical Co. or
Fluka. Unless otherwise noted all commercial materials (si-
lanes, ketones and aldehydes) were used without purifica-
tion. H, 11B, 31P and 13C{1H} NMR spectra were recorded on
1
a Varian Gemini 300 (299.78 MHz), or on a Varian Mercury
200 (199.78 MHz) spectrometer. GC-MS analyses were car-
ried out on a CP-3800 Saturn 2000 MS/MS spectrometer
(CP-Sil8CB low bleed/MS 30 m, ID 0.25 mm, OD 0.39 mm,
Film thickness 0.25 mm from Chrompack).
General Procedure for the Catalytic Hydrosilylations
according to Tables 1–4
A solution of the appropriate substrates (0.5 mmol) and the
silanes (0.6 mmol) and the given catalytic amount of the
rhenium complex in the given solvent (0.8 mL) was stirred
for an appropriate period of time at room temperature
under a nitrogen atmosphere. Upon completion, the reac-
tion the mixture was filtered over celite. The resulting solu-
tion was analyzed by NMR spectroscopy or GC-MS. The
obtained NMR data of the silyl ethers were identical to
those of the literatures.[3d,8a,f,g] The yields are listed in
Table 1, Table 2, Table 3 and Table 4. The GC-MS analysis
furnished the retention time listed in the following (tR =re-
tention time, CH2Cl2 was used as the sovlent): triethyl(iso-
propoxy)silane: m/z=174.1, tR =2.73 min; sec-butoxytri-
ACHTUNGTRENNUNG
ACHTUNGTRENNUNG
ACHTUNGTRENNUNG
General Procedure for the Catalytic Hydrosilylations
of Table 5
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Appropriate amounts of the substrate (2.5 mmol), silane
(3.75 mmol) and catalytic amounts of the rhenium complex
(0.2 mmol%) in chlorobenzene were placed a Young tap
Schlenk tube according to the procedures of the hydrosilyla-
tions of Tables 1–4. The reaction mixture was heated to
858C and stirred for the required reaction time. Upon com-
pletion, the reaction mixture was filtered over Celite. The
resulting solution was analyzed by NMR spectroscopy. The
found resonances were in accord with those of the literature.
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1
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The yields were determined by integration of the H NMR
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Acknowledgements
We gratefully acknowledge financial support from the Swiss
National Science Foundation and the funds of the University
of Zurich.
Adv. Synth. Catal. 2009, 351, 1783 – 1788
ꢂ 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
1787