A new method for the electrophilic fluorination of vinyl stannanes.

Matthews, Donald P.; Miller, Shawn C.; Jarvi, Esa T.; Sabol, Jeffrey S.; McCarthy, James R.

doi:10.1016/s0040-4039(00)93378-1

Cited by 87 publications

(30 citation statements)

References 10 publications

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“…Equally gratifying is the compatibility with functional groups such as aldehydes, esters, enoates, nitriles, phthalimide and even silyl ethers. These common protecting groups are endangered by any recipe that comprises nucleophilic anions (most notably fluoride) or eventually releases acids such as HOTf or HF; moreover, they are cleaved when F‐TEDA‐BF 4 alone is used as [F + ] source . Likewise, the sensitive doubly allylic alcohol in 10 proved stable and the pre‐existing alkene passed uncompromised.…”

Section: Methodsmentioning

confidence: 99%

Stereospecific Synthesis of Fluoroalkenes by Silver‐Mediated Fluorination of Functionalized Alkenylstannanes

Sommer

Fürstner

2016

Chemistry A European J

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The known procedures for the conversion of alkenylstannanes into the corresponding fluoroalkenes suffer from largely variable yields and a limited compatibility with functional groups; most notably, protodestannation becomes a serious issue whenever protic sites are present in the substrate. Outlined in this paper is a convenient alternative with a much improved application profile, which is largely unperturbed by free alcohols and amides of all sorts. Key to success is the use of F-TEDA-PF6 in combination with non-hygroscopic and bench-stable silver phosphinate (AgOP(O)Ph₂) that acts as an essentially neutral, non-nucleophilic promotor and effective tin-scavenger at the same time. This new method opens many opportunities for late-stage fluorination of elaborate compounds far beyond the scope of the literature procedures, as witnessed by the preparation of a fluorinated macrolide antibiotic, a fluorinated prostaglandin derivative, and a set of fluorinated amino acid surrogates and peptide isosteres

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Section: Methodsmentioning

confidence: 99%

Stereospecific Synthesis of Fluoroalkenes by Silver‐Mediated Fluorination of Functionalized Alkenylstannanes

Sommer

Fürstner

2016

Chemistry A European J

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“…Vinyl stannanes can react with 1 in the absence of silver, 12 but the reaction rate can be increased using Ag(I) salts.…”

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confidence: 99%

Silver-Mediated Fluorination of Functionalized Aryl Stannanes

2009

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“…[41] McCarthy and co-workers also reported the electrophilic fluorination of the alkenylstannane 23a with Selectfluor TM . [42] Ag-mediated fluorination of alkenylstannanes proceeded in a highly stereospecific manner. In 1992, Tius and coworker reported that the alkenyltrimethylstannane 23b reacts with XeF 2 in the presence of stoichiometric amounts of AgPF 6 to give the corresponding fluoro-olefin in 24-52 % yields (Scheme 22).…”

Section: Fluorination Of Alkenyl Metallic Speciesmentioning

confidence: 99%

Synthetic Methods for Fluorinated Olefins

2011

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Fluoro‐olefin compounds, because of their favorable physicochemical properties, have been used as key materials in the fields of medicinal chemistry, chemical biology, and materials sciences. A number of the synthetic methodologies for applications of fluoro‐olefin compounds were developed simultaneously. This review article provides an overview not only of recent progress in syntheses of fluoro‐olefin compounds but also of some classical but still valuable synthetic reactions.

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A new method for the electrophilic fluorination of vinyl stannanes.

Cited by 87 publications

References 10 publications

Stereospecific Synthesis of Fluoroalkenes by Silver‐Mediated Fluorination of Functionalized Alkenylstannanes

Stereospecific Synthesis of Fluoroalkenes by Silver‐Mediated Fluorination of Functionalized Alkenylstannanes

Silver-Mediated Fluorination of Functionalized Aryl Stannanes

Synthetic Methods for Fluorinated Olefins

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