79271-56-0

Usage

Uses

Used in Chemical Synthesis:
Triethylsilyl trifluoromethanesulfonate is used as a silylating agent for the protection of alcohols during chemical synthesis. Its increased stability towards hydrolysis compared to trimethylsilyl ethers makes it a preferred choice for protecting sensitive alcohol groups.
Used as a Lewis Acid Catalyst:
In the capacity of a Lewis acid catalyst, triethylsilyl trifluoromethanesulfonate facilitates various condensation reactions, such as the reaction of 2-trimethylsiloxyfuran with aldehydes, leading to the formation of threo addition products.
Used in the Preparation of Diazo Compounds:
Triethylsilyl trifluoromethanesulfonate is utilized in the synthesis of 1-diazo-3,3-dimethyl-1-(triethylsilyl)-2-butanone from 1-diazo-3,3-dimethyl-butan-2-one, showcasing its versatility in organic chemistry.
Used in Overcoming Steric Hindrance:
In cases where steric hindrance prevents the silylation of hydroxyl groups using Et3SiCl, triethylsilyl trifluoromethanesulfonate is employed to effectively address this challenge, allowing for the successful protection of sterically hindered alcohols.

Preparation

Triethylsilyl Trifluoromethanesulfonate can be prepared by reacting chlorotriethylsilane with trifluoromethanesulfonic acid followed by distillation.

InChI:InChI=1/C7H15F3O3SSi/c1-4-15(5-2,6-3)13-14(11,12)7(8,9)10/h4-6H2,1-3H3

Upstream product

• 994-30-9 triethylsilyl chloride 
• 1493-13-6 trifluorormethanesulfonic acid 
• 617-86-7 triethylsilane 
• 66469-45-2 Silantetrayltetrakis(trifluormethansulfonat) 

Downstream Products

• 136758-68-4 Triethyl-((E)-1-methyl-4-phenyl-but-3-enyloxy)-silane 
• 170890-07-0 C₅₇H₉₄O₁₀Si₂ 
• 164118-35-8 <5(2E,4S,6S),7S>-2,7-Anhydro-8,9,10,12,13-pentadeoxy-11-ethanoate-10-methylene-3,4-bis-C-<(phenylmethoxy)carbonyl>-12-(phenylmethyl)-6-O-(triethylsilyl)-5-(4,6-dimethyl-2-octenoate)-L-erythro-L-glycero-D-altro-7-trideculo-7,4-furanosonic acid phenylm... 
• 164118-33-6 <5(2E,4S,6S),7S>-2,7-Anhydro-8,9,10,12,13-pentadeoxy-11-O-<(4-methoxyphenyl)methyl>-10-methylene-3,4-bis-C-<(phenylmethoxy)carbonyl>-12-(phenylmethyl)-6-O-(triethylsilyl)-5-(4,6-dimethyl-2-octenoate)-L-erythro-L-glycero-D-altro-7-trideculo-7,4-furano... 
• 18406-24-1 1-(triethylsilyloxy)-4-methoxybenzene 
• 261918-93-8 Trifluoro-methanesulfonic acid (2R,3R,4R,5S,6S)-6-allyl-5-allyloxy-4-(4-methoxy-benzyloxy)-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester 
• 288088-66-4 C₂₉H₄₃NO₈Si 
• 288088-75-5 C₂₉H₄₃NO₈Si 
• 222406-39-5 <5-<5--4-methoxytetrahydropyran-2-yloxy>-2-methyl-6-(2-nitrobenzyloxy)-4-(triethylsilyloxy)tetrahydropyran-3-ylidene>acetic acid ethyl ester 
• 222406-72-6 N-isopropyl-N-<4-metoxy-6-<6-methyl-5-methylsulfanyl-2-(2-nitrobenzyloxy)-4-(triethylsilyloxy)-5-vinyltetrahydropyran-3-yloxy>tetrahydropyran-3-yl>carbamic acid 9H-fluoren-9-ylmethyl ester 
• 220484-33-3 (E)-(3S,6R)-6-{(4S,6R)-6-[(E)-(R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-non-1-enyl]-2,2,5,5-tetramethyl-[1,3]dioxan-4-yl}-4-methyl-3-triethylsilanyloxy-hept-4-enoic acid phenyl ester 
• 214827-37-9 (2S,3S,5S,6R)-2-(2-Benzenesulfonyl-1,1-dimethyl-ethyl)-2-methoxy-3,5-bis-triethylsilanyloxy-4-[2-triethylsilanyloxy-eth-(E)-ylidene]-6-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-pyran 
• 221684-57-7 methyl 2,2-dimethoxy-3-(triethylsilyl)oxy-3-<(Z)-hexa-1,5-diyne-3-ene>cyclohex-4,6-diene-1-carboxylate 
• 129834-74-8 4-<<3-O-methyl-2,4-bis-O-(triethylsilyl)-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoic acid 

Relevant academic research and scientific papers

Heterolytic activation of H-X (X = H, Si, B, and C) bonds: An experimental and theoretical investigation

The highly electrophilic, coordinatively unsaturated, 16-electron [Ru(P(OH)3)(dppe)2][OTf]2 (dppe = Ph 2PCH2CH2PPh2) complex 1 activates the H-H, the Si-H, and the B-H bonds, in H2(g), EtMe2SiH and Et3SiH, and H3B·L (L = PMe3, PPh3), respectively, in a heterolytic fashion. The heterolysis of H2 involves an η2-H2 complex (observable at low temperatures), whereas the computations indicate that those of the Si-H and the B-H bonds proceed through unobserved η1-species. The common ruthenium-containing product in these reactions is trans-[Ru(H)(P(OH) 3)(dppe)2][OTf], 2. The [Ru(P(OH)3)(dppe) 2][OTf]2 complex is unique with regard to activating the H-H, the Si-H, and the B-H bonds in a heterolytic manner. These reactions and the heterolytic activation of the C-H bond in methane by the model complex [Ru(POH)3)-(H2PCH2CH2PH 2)2][CI][OTf], 4, have been investigated using computational methods as well, at the B3LYP/ LANL2DZ level. While the model complex activates the H-H, the Si-H, and the B-H bonds in H2, SiH4, and H3B·L (L = PMe3, PPh 3), respectively, with a low barrier, activation of the C-H bond in CH4 involves a transition state of 57.5 kcal/mol high in energy. The inability of the ruthenium complex to activate CH4 is due to the undue stretching of the C-H bond needed at the transition state, in comparison to the other substrates.

Silicon Tetrakis(trifluoromethanesulfonate): A Simple Neutral Silane Acting as a Soft and Hard Lewis Superacid

A facile synthesis and isolation of pristine silicon tetrakis(trifluoromethanesulfonate), Si(OTf)4, is reported, acting as the first neutral silicon-based Lewis superacid suitable towards soft and hard Lewis bases. Its OTf groups have a dual function: they are excellent leaving groups and modulate the degree of reactivity towards soft and hard Lewis bases. Exposed to soft Lewis donors, Si(OTf)4 leads to [L2Si(OTf)4] complexes (L=isocyanide, thioether and carbonyl compounds) with retention of all Si?OTf bonds. In contrast, it can cleave C?X bonds (X=F, Cl) of hard organic Lewis bases with a high tendency to form SiX4 (X=F, Cl) after halide/triflate exchange. Most notable, Si(OTf)4 allows a gentle oxydefluorination of mono- and bis(trifluoromethyl)benzenes, resulting in the formation of the corresponding benzoylium species, which are stabilized by the weakly coordinating [Si(OTf)6] dianion.

Zinc-catalyzed silylation of terminal alkynes

(Chemical Equation Presented) A rapid and high-yielding silylation of terminal alkynes employing TMSOTf and catalytic quantities of Zn(OTf) 2 has been developed. The reaction works well for a variety of substrates including reactive esters. Fifteen examples with yields of >90% are reported.

Process for producing novel naphthyridine derivatives

A novel naphthyridine derivative showing high activity as a tachykinin receptor antagonist can be produced at high efficiency by reacting an acylating agent such as a carboxylic acid derivative with a compound represented by the formula (1): wherein R1, R2 and R3 represent independently a hydrogen atom, a lower alkyl group, a lower alkoxyl group, an aryl group, a heteroaryl group, an amino group, etc., and X1 and X2 represent respectively a halogen atom.

Lewis acid mediated Peterson fluoroolefination

Peterson olefination of the alkyl and aryl aldehydes with C,O-bis(triethylsilyl)fluoroketene acetal 1 promoted by titanium tetrachloride and dimethylaluminum chloride was investigated. Desired fluoroolefins were formed with high stereoselectivity and moderate to high yields.