Trialkylsilyl Perfluoroalkanesulfonates: Highly Reactive Silylating Agents and Lewis Acids in Organic Synthesis

Emde, H.; Domsch, Dietmar; Feger, Harry; Frick, Ulrich; Götz, Andreas W.; Hergott, H. H.; Hofmann, K. A.; Kober, W.; Krägeloh, Konrad; Oesterle, Thomas; Steppan, Wolfgang; West, W.; Simchen, Gerhard

doi:10.1055/s-1982-29685

Cited by 244 publications

(85 citation statements)

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“…The excellent silylation properties 46,47 of these substances prompted us to elaborate syntheses for functional substituted and branched poly [5,5'-(silylene)-2,2'-dithienylene]s via silyl triflate intermediates. We obtained the parent compounds from silyl bis(triflates) and 5,5'-dilithio-2,2'-dithiophene (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and functionalization of Poly[5,5′-(silylene)-2,2′-dithienylene]s using silyl triflate intermediates†

Uhlig

1999

Appl. Organometal. Chem.

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Section: Resultsmentioning

confidence: 99%

Synthesis and functionalization of Poly[5,5′-(silylene)-2,2′-dithienylene]s using silyl triflate intermediates†

Uhlig

1999

Appl. Organometal. Chem.

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“…A reaction occurred between the nucleophile and the imine-triflate complex that yielded a tetracyclic product without isolation of a tricyclic intermediate. Triinethylsilyl trifluoromethanesulfonate has been used previously as a powerful silylating agent for a wide range of active hydrogen compounds (21) and also for converting imines to the corresponding enamines (22,23) in the presence of alkylamine bases. To our knowledge, its use to activate an imine toward nucleophilic addition has not been reported prior to its use by us (1, 11).…”

Section: Resultsmentioning

confidence: 99%

8H-Isoquino[2,1-b][2,7]naphthyridin-8-ones: synthesis of the Alangium alkaloids, alangimaridine and alangimarine

Jahangir¹,

Brook²,

MacLean³

et al. 1987

Can. J. Chem.

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. 65, 2362 (1987).It is shown that 3,4-dihydroisoquinolines are activated toward nucleophilic attack by reaction with trimethylsilyl trifluoromethanesulfonate. The complex so formed reacts readily with the lithio derivative of 3-cyano-4-methyl-5-vinylpyridine, affording in a single step a tetracyclic amidine from which a lacta'm is obtained by hydrolysis. These reactions have been applied to the synthesis of the Alangium alkaloids, (2) On demontre que les dihydro-3,4 isoquinoliines sont activees par rapport aux rCactions nucleophiles avec le trifluoromethanesulfonate de trimethylsilyle. Le complexe qui se forme ainsi rCagit facilement avec le dCrivC lithien de la cyano-3 methyl-4 vinyl-5 pyridine pour conduire en une seule Ctape a une amidine tetracyclique a partir de laquelle on peut obtenir une lactame par hydrolyse. On a applique ces reactions a la synthkse des alcaloi'des suivants de 1'Alnngium (*)-alangimaridine et alangimarine.[Traduit par la revue]

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“…Subsequently the silicon atom reacts with heteroatoms, especially oxygen to form onium ions. In contrast to more conventional Lewis acids such as AlCl 3 and TiCl 4 , TMSOTf tends to bind to a single hetero functional group. TMSOTf is 6.7 × 10 8 times more reactive than TMSCl, and this is manifested in an extreme sensitivity towards moisture which must be excluded from all reactions.…”

Section: Trifluoromethanesulfonate (Tmsotf) Introductionmentioning

confidence: 99%

“…2 The ability of TMSOTf to form supercationic species with organic substrates results in it's utilization in a wide range of synthetic applications. 3 TMSOTf, 4 is prepared by the gradual addition of chlorotrimethylsilane to trifluoromethanesulfonic acid with stirring and protection from moisture. The mixture is heated until hydrogen chloride evolution ceases and then the product is isolated by fractional distillation.…”

Section: Trifluoromethanesulfonate (Tmsotf) Introductionmentioning

confidence: 99%

Trimethylsilyl Trifluoromethanesulfonate (TMSOTf)

Goundry¹

2003

Synlett

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This feature focuses on a reagent chosen by a postgraduate, highlighting the uses and preparation of the reagent in current research SPOTLIGHT 1940 Trimethylsilyl Trifluoromethanesulfonate (TMSOTf) Compiled by William R. F. Goundry William Goundry was born in Chelmsford (UK) in 1978. In 2001 he completed his undergraduate course with a research project on the synthesis of marine sponge alkaloids to receive his MChem degree. He has carried on working in the same research group under the supervision of Professor J. E. Baldwin and Dr Victor Lee, and is currently in the second year of his DPhil studies.

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Trialkylsilyl Perfluoroalkanesulfonates: Highly Reactive Silylating Agents and Lewis Acids in Organic Synthesis

Cited by 244 publications

References 0 publications

Synthesis and functionalization of Poly[5,5′-(silylene)-2,2′-dithienylene]s using silyl triflate intermediates†

Synthesis and functionalization of Poly[5,5′-(silylene)-2,2′-dithienylene]s using silyl triflate intermediates†

8H-Isoquino[2,1-b][2,7]naphthyridin-8-ones: synthesis of the Alangium alkaloids, alangimaridine and alangimarine

Trimethylsilyl Trifluoromethanesulfonate (TMSOTf)

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