Trimethylsilyl trifluoromethanesulfonate
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| Names | |
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| IUPAC name
trimethylsilyl trifluoromethanesulfonate
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| Other names
TMSOTf
Trimethylsilyl triflate TMS triflate Trifluoromethanesulfonic acid trimethylsilyl ester | |
| Identifiers | |
3D model (JSmol)
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| ECHA InfoCard | 100.044.136 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C4H9F3O3SSi | |
| Molar mass | 222.26 g/mol |
| Appearance | colourless liquid |
| Density | 1.225 g/mL |
| Boiling point | 140 °C (760 Tor) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Trimethylsilyl trifluoromethanesulfonate is a trifluoromethanesulfonate derivate with a trimethylsilyl R-group. It has similar reactivity to trimethylsilyl chloride, and is also used often in organic synthesis.[1]
Illustrative reactions
A common application is the conversion of ketones and aldehydes to silyl enol ethers.[2]
The stereoselective synthesis of seven benzylated proanthocyanidin trimers (epicatechin-(4β-8)-epicatechin-(4β-8)-epicatechin trimer (procyanidin C1), catechin-(4α-8)-catechin-(4α-8)-catechin trimer (procyanidin C2), epicatechin-(4β-8)-epicatechin-(4β-8)-catechin trimer and epicatechin-(4β-8)-catechin-(4α-8)-epicatechin trimer derivatives) can be achieved with TMSOTf-catalyzed condensation reaction, in excellent yields. Deprotection of (+)-catechin and (−)-epicatechin trimers derivatives gives four natural procyanidin trimers in good yields.[3]
It has been used in Takahashi Taxol total synthesis or for chemical glycosylation reactions.[4]
Trimethylsilyl trifluoromethanesulfonate is used to install tert-alkyl groups on phosphine (R = alkyl):[5]
- PH3 + R3C–OAc + Me3SiOTf → [(R3C)2PH2]OTf
Related reagents
Trimethylsilyl trifluoromethanesulfonate is a source of trimethylsilyl cation. Other more potent sources silylium cations are known.[more detail needed]
See also
References
- ^ "Trimethylsilyl Trifluoromethanesulfonate". Encyclopedia of Reagents for Organic Synthesis. 2018. doi:10.1002/047084289X.rt338. ISBN 978-0471936237.
{{cite journal}}: Cite uses deprecated parameter|authors=(help) - ^ Umemoto, Teruo; Tomita, Kyoichi; Kawada, Kosuke (1990). "N-Fluoropyridinium Triflate: An Electrophilic Fluorinating Agent". Organic Syntheses. 69: 129. doi:10.15227/orgsyn.069.0129.
- ^ Efficient Stereoselective Synthesis of Proanthocyanidin Trimers with TMSOTf-Catalyzed Intermolecular Condensation. Akiko Saito, Akira Tanaka, Makoto Ubukata and Noriyuki Nakajima, Synlett, 2004, volume 6, pages 1069-1073, doi:10.1055/s-2004-822905
- ^ Love, Kerry R.; Seeberger, Peter H. (2005). "Synthesis and Use of Glycosyl Phosphates as Glycosyl Donors". Organic Syntheses. 81: 225. doi:10.15227/orgsyn.081.0225.
- ^ Barber, Thomas; Argent, Stephen P.; Ball, Liam T. (2020-05-15). "Expanding Ligand Space: Preparation, Characterization, and Synthetic Applications of Air-Stable, Odorless Di- tert -alkylphosphine Surrogates". ACS Catalysis. 10 (10): 5454–5461. doi:10.1021/acscatal.0c01414. ISSN 2155-5435.
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