Phosphonodifluoromethyl and Phosphonothiodifluoromethyl Radicals. Generation and Addition onto Alkenes and Alkynes

Pignard, Sébastien; Lopin, Chrystel; Gouhier, Géraldine; Piettre, Serge R.

doi:10.1021/jo051511c

Cited by 31 publications

(12 citation statements)

References 39 publications

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“…Iodo phosphorus compounds 2b, [27] 2e, [6b] 2g, [6b] and 5 [6b] were prepared according to known methods, and these compounds are reported. Iodo phosphorus compounds 2c, [27] 2d, [27] 2f, [27] and 2h [28] were prepared according to known methods. Diethyl (iodomethyl)phosphonate (2a), benzophenone, and cyclohexanone are commercially available.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Cyclopropane‐Containing Phosphorus Compounds by Radical Coupling of Butenylindium with Iodo Phosphorus Compounds

et al. 2011

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The radical coupling of α-or β-iodo phosphorus compounds such as iodo phosphonate, iodo phosphane oxide, and iodo phosphonothioate with butenylindium species, prepared by transmetalation between a (cyclopropylmethyl)stannane and InBr 3 , afforded the corresponding cyclopropylmethylated products. The radical reaction was initiated by the radical species generated from butenylindium assisted by a small amount of oxygen. Butenylindium works not only as a cyclopropylmethylating reagent, but also as a radical initiator. For

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Section: Methodsmentioning

confidence: 99%

Synthesis of Cyclopropane‐Containing Phosphorus Compounds by Radical Coupling of Butenylindium with Iodo Phosphorus Compounds

et al. 2011

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“…The phosphonodifluoromethylation of alkenes has been documented to proceed through diverse methods such as nucleophilic addition [47][48][49][50][51][52][53][54], transition metal catalysis [55][56][57][58], photoredox catalysis (by oxidative quenching cycles) [59][60][61][62][63], or radical ATRA reactions [64][65][66][67][68][69], as depicted in Scheme 15.…”

Section: Difluoromethylation Of Aliphatic Carbon-carbon Multiple Bondsmentioning

confidence: 99%

Photocatalytic Difluoromethylation Reactions of Aromatic Compounds and Aliphatic Multiple C–C Bonds

Barata‐Vallejo

Postigo

2019

Molecules

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Among the realm of visible light photocatalytic transformations, late-stage difluoromethylation reactions (introduction of difluoromethyl groups in the last stages of synthetic protocols) have played relevant roles as the CF2X group substitutions exert positive impacts on the physical properties of organic compounds including solubility, metabolic stability, and lipophilicity, which are tenets of considerable importance in pharmaceutical, agrochemical, and materials science. Visible-light-photocatalyzed difluoromethylation reactions are shown to be accomplished on (hetero)aromatic and carbon–carbon unsaturated aliphatic substrates under mild and environmentally benign conditions.

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“…The (TMS) 3 SiH-mediated addition of fluoroalkyl radicals to alkenes has also been reported [ 48 , 49 ]. The addition of perfluoroalkyl iodides or bromides to a variety of alkenes afforded the expected adducts 42 with moderate to good yields in water as the solvent ( Scheme 18 ) [ 48 ].…”

Section: (Tms) 3 Sih As Mediator Of Consecutivementioning

confidence: 99%

Recent Applications of the (TMS)3SiH Radical-Based Reagent

Chatgilialoglu

Lalevée

2012

Molecules

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This review article focuses on the recent applications of tris(trimethylsilyl)silane as a radical-based reagent in organic chemistry. Numerous examples of the successful use of (TMS)3SiH in radical reductions, hydrosilylation and consecutive radical reactions are given. The use of (TMS)3SiH allows reactions to be carried out under mild conditions with excellent yields of products and remarkable chemo-, regio-, and stereoselectivity. The strategic role of (TMS)3SiH in polymerization is underlined with emphasis on the photo-induced radical polymerization of olefins and photo-promoted cationic polymerization of epoxides.

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Phosphonodifluoromethyl and Phosphonothiodifluoromethyl Radicals. Generation and Addition onto Alkenes and Alkynes

Cited by 31 publications

References 39 publications

Synthesis of Cyclopropane‐Containing Phosphorus Compounds by Radical Coupling of Butenylindium with Iodo Phosphorus Compounds

Synthesis of Cyclopropane‐Containing Phosphorus Compounds by Radical Coupling of Butenylindium with Iodo Phosphorus Compounds

Photocatalytic Difluoromethylation Reactions of Aromatic Compounds and Aliphatic Multiple C–C Bonds

Recent Applications of the (TMS)3SiH Radical-Based Reagent

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