Dehydrogenative Silylation of Terminal Alkynes with Hydrosilanes under Zinc–Pyridine Catalysis
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Experimental Section
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General Procedure
ZnACHTUNGTRENNUNG(OTf)2 [(7.27 mg, 20.0 mmol) or (14.5 mg, 40.0 mmol)] was
placed in a 20-mL Schlenk tube, which was heated at 1508C
under vacuum for 2 h. The tube was cooled down to room
temperature and filled with argon. EtCN (0.40 mL) was
added to the tube and then the mixture was stirred at room
temperature for 3 min. To this were added alkyne
1
(0.400 mmol), hydrosilane 2 (0.600, 0.800, 1.20 or
1.60 mmol) and pyridine [(6.3 mg, 0.080 mmol) or (15.8 mg,
0.200 mmol)] successively, and the resulting mixture was
stirred at 1008C. After the time specified in Table 2, a satu-
rated aqueous NH4Cl solution (0.5 mL) was added to the
mixture, and the aqueous phase was extracted with EtOAc
(5 mLꢁ3). The combined organic layer was washed with
brine (1 mL) and then dried over anhydrous sodium sulfate.
Filtration and evaporation of the solvent followed by
column chromatography on silica gel gave the corresponding
product (3).
Acknowledgements
Partial financial support by a Grant-in-Aid for Scientific Re-
search (No. 24550123) from the Ministry of Education, Cul-
ture, Sports, Science and Technology is highly acknowledged.
We greatly appreciate Dr. Go Hirai as well as Prof. Dr.
Mikiko Sodeoka at RIKEN, Japan, for their helpful support
in HR-MS measurements.
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2963