Radikalische Vinylierung von Iodiden und Dithiocarbonaten

Bertrand, Frédérique; Quiclet‐Sire, Béatrice; Zard, Samir Z.

doi:10.1002/(sici)1521-3757(19990712)111:13/14<2135::aid-ange2135>3.0.co;2-x

Cited by 18 publications

References 24 publications

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Tin-Free Radical Acylation Reactions with Methanesulfonyl Oxime Ether

et al. 2001

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Recent advances in radical reactions have greatly benefited from the efficiency of organotin reagents as mediators. However, organotin reagents are highly toxic, and it is difficult to remove their residues from the products. These disadvantages have proved to be a serious barrier to industrial applications. To solve the problems associated with toxic organotin reagents, several alternative approaches, including the use of polymer-supported organotin reagents and organosilanes, have been utilized with some success. [1] Recently, a few tin-free carbon ± carbon bond-forming reactions were reported; they include organosulfone-mediated radical allylation, alkenylation, alkynylation, and azidation reactions. [2±4] Recently, we reported highly efficient tin-mediated radical acylation reactions with sulfonyl oxime ethers [Eq. ( 1)]. [5] We then studied the possibility of environmentally benign tin-free

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Tin-Free Radical Acylation Reactions with Methanesulfonyl Oxime Ether

et al. 2001

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Tin‐Free Radical‐Mediated CC‐Bond Formations with Alkyl Allyl Sulfones as Radical Precursors

Kim

Lim

2002

Angewandte Chemie

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Tin-Free Radical Acylation Reactions with Methanesulfonyl Oxime Ether

Kim

Song

Choi

et al. 2001

Angew. Chem. Int. Ed.

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A simple strategy involving thermal decomposition of the methanesulfonyl radical into the methyl radical and the subsequent transfer of an iodine atom or phenyl telluride group was used to develop a tin‐free radical acylation reaction (see scheme; V‐40=1,1′‐azobis(cyclohexane‐1‐carbonitrile). The key was finding reaction conditions under which the I or PhTe transfer is faster than the direct addition of the alkyl radical to the methanesulfonyl oxime ether.

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Radikalische Vinylierung von Iodiden und Dithiocarbonaten

Cited by 18 publications

References 24 publications

Tin-Free Radical Acylation Reactions with Methanesulfonyl Oxime Ether

Tin-Free Radical Acylation Reactions with Methanesulfonyl Oxime Ether

Tin‐Free Radical‐Mediated CC‐Bond Formations with Alkyl Allyl Sulfones as Radical Precursors

Tin-Free Radical Acylation Reactions with Methanesulfonyl Oxime Ether

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