Fluorinated organometallics: Vinyl, alkynyl, allyl, benzyl, propargyl and aryl

Burton, Donald J.; Yang, Zhen‐Yu; Morken, Peter A.

doi:10.1016/s0040-4020(01)81105-4

Cited by 133 publications

(57 citation statements)

References 278 publications

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“…[24] The artificial pyrethroids bifenthrin and cyhalothrin, both of which contain CH = C(Cl)CF 3 in lieu of CH = CMe 2 or CH = CCl 2 , are highly potent, exhibiting remarkably enhanced activity relative to nonfluorinated congeners (Figure 4). [25] We have established a practical and stereocontrolled approach to di-and trifluorinated synthetic pyrethroids based on the addition of CF 3 CCl 2 ZnCl to aldehydes and reductive olefination of the adducts.…”

Section: Fluorine-containing Polyhaloalkyl Metal Reagentsmentioning

confidence: 99%

Modern Synthetic Methods for Fluorine‐Substituted Target Molecules

Shimizu¹,

Hiyama²

2004

Angew Chem Int Ed

786

170

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Fluorine has come to be recognized as a key element in materials science: in heat-transfer agents, liquid crystals, dyes, surfactants, plastics, elastomers, membranes, and other materials. Furthermore, many fluorine-containing biologically active agents are finding applications as pharmaceuticals and agrochemicals. Progress in synthetic fluorine chemistry has been critical to the development of these fields and has led to the invention of many novel fluorinated molecules as future drugs and materials. As a result of the electronic effects of fluorine substituents, fluorinated substrates and reagents often exhibit unusual and unique chemical properties, which often make them incompatible with established synthetic methods. Thus, the problem of how to control the unusual properties of compounds with fluorine substituents deserves much attention, so as to promote the design of facile, efficient, and environmentally benign methods for the synthesis of valuable organofluorine targets.

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Section: Fluorine-containing Polyhaloalkyl Metal Reagentsmentioning

confidence: 99%

Modern Synthetic Methods for Fluorine‐Substituted Target Molecules

Shimizu¹,

Hiyama²

2004

Angew Chem Int Ed

786

170

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“…Normant and co-workers generated various fluorovinylzinc reagents including a-chloro-b-fluorovinylzinc reagent by the metallation of halo or hydro fluoroalkenes via the corresponding vinyllithium species [12][13][14][15][16]. But fluorinated vinyllithiums are thermally unstable and need to be generated at very low temperature in order to have reasonable yield of the zinc reagent [17][18][19].…”

Section: Introductionmentioning

confidence: 99%

Room temperature preparation of α-chloro-β,β-difluoroethenylzinc reagent (CF2CClZnCl) by the metallation of HCFC-133a (CF3CH2Cl) and a high yield one-pot synthesis of α-chloro-β,β-difluorostyrenes

Anilkumar

Burton

2005

Journal of Fluorine Chemistry

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“…55 The first example of a perfluoroarylsilver compound was reported by Miller and Sun in 1970. 49 Reaction of perfluorophenyllithium with silver trifluoroacetate, or of perfluorophenyl bromide with perfluoroisopropylsilver, gave perfluorophenylsilver as colorless crystals (Scheme 1.17).…”

Section: Synthesis and Stability Of Perfluoroarylsilver Compoundsmentioning

confidence: 99%