- Activation of Carbon Dioxide by Silyl Triflate-Based Frustrated Lewis Pairs
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Silyl triflates of the form R4-nSi(OTf)n (n=1, 2; OTf=OSO3CF3) are shown to activate carbon dioxide when paired with bulky alkyl-substituted Group15 bases. Combinations of silyl triflates and 2,2,6,6-tetramethylpiperidine react with CO2 to afford silyl carbamates via a frustrated Lewis pair-type mechanism. With trialkylphosphines, the silyl triflates R3Si(OTf) reversibly bind CO2 affording [R′3P(CO2)SiR3][OTf] whereas when Ph2Si(OTf)2 is used one or two molecules of CO2 can be sequestered. The latter bis-CO2 product is favoured at low temperatures and by excess phosphine.
- Weicker, Sarah A.,Stephan, Douglas W.
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p. 13027 - 13034
(2015/09/07)
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- Improved preparation of N-trimethylsilylpyridinium triflate, N- triphenylsilylpyridinium triflate, N-triisopropylsilylpyridinium triflate and their use in silylating alcohols to silyl ethers
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N-Silylpyridinium triflates 1a-c have been prepared in excellent yield from the corresponding allyl silanes by reaction with triflic acid followed by pyridine. Compounds 1a-c were used to prepare silyl ethers from alcohols in generally high yield. A convenient procedure has been developed which enables the silylation of alcohols without an aqueous workup in the product isolation.
- Olah, George A.,Klumpp, Douglas A.
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p. 744 - 746
(2007/10/03)
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