Arylphosphonylation and Arylazidation of Activated Alkenes

Kong, Wangqing; Merino, Estı́baliz; Nevado, Cristina

doi:10.1002/ange.201311241

Cited by 67 publications

(19 citation statements)

References 121 publications

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“…In 2014, Nevado and co-workers further exploited the potential of benziodoxolone 9 for the generation of azide radicals. [33] They developed the aryl azidation of acrylamides based on the internal transfer of an aryl group on as ulfonamide (Scheme 8). b-Azido amides 55-57 bearing an allcarbon quaternary center in the a-position were obtained in 72-75 %y ield.…”

Section: C-n Bond Formationmentioning

confidence: 99%

Cyclic Hypervalent Iodine Reagents for Atom‐Transfer Reactions: Beyond Trifluoromethylation

et al. 2016

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Hypervalent iodine compounds are privileged reagents in organic synthesis because of their exceptional reactivity. Among these compounds, cyclic derivatives stand apart because of their enhanced stability. They have been widely used as oxidants, but their potential for functional‐group transfer has only begun to be investigated recently. The use of benziodoxol(on)es for trifluoromethylation (Togni's reagents) is already widely recognized, but other transformations have also attracted strong interest recently. In this Review, the development in the area since 2011 will be presented. After a short summary of synthetic methods to prepare benziodoxol(on)e reagents, their use to construct carbon–heteroatom and carbon–carbon bonds will be presented. In particular, the introduction of alkynes by using ethynylbenziodoxol(on)e (EBX) reagents has been highly successful. Breakthroughs in the introduction of alkoxy, azido, difluoromethyl, and cyano groups will also be described.

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Section: C-n Bond Formationmentioning

confidence: 99%

Cyclic Hypervalent Iodine Reagents for Atom‐Transfer Reactions: Beyond Trifluoromethylation

et al. 2016

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“…For instance, they have recently been used for the zinc-catalyzed azidation of silyl enol ethers, [20] the intermolecular [21] and intramolecular [22] oxyazidationo fa lkenes, the copper-catalyzed oxoazidation of indoles, [23] and the arylazidation of activated alkenes. [24] Based on our previous studiesw ith enamides,w et hought that it would be more general and satisfying to develop as et of conditions for the umpolung of pseudohalides that would only differ by the natureo ft he salts. [25]…”

Section: Introductionmentioning

confidence: 99%

Iodine(III)‐Mediated Diazidation and Azido‐oxyamination of Enamides

Nocquet‐Thibault

Rayar

Retailleau

et al. 2015

Chemistry A European J

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In this study we demonstrate that the combination of bis(tert-butylcarbonyloxy)iodobenzene and lithium azide in acetonitrile allows the diazidation of various enamide substrates. The azido-oxyamination of the same substrates can be carried out in the presence of 2,2,6,6-tetramethylpiperidine N-oxide (TEMPO). Control experiments strongly suggest that this latter process occurs through a shift in nature of the in situ generated electrophilic species from a radical to a cation. Finally, the versatility of the novel compounds synthesized was also assessed by running various selective reactions on them.

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“…Rearomatization accompanied by extrusion of SO 2 and H abstraction by the amidyl radical intermediates IV and IV′ delivers the observed indanes 3 / 5 or dibenzocycloheptadienes 7 / 8 , respectively. In the case of the silver‐catalyzed phosphonylation reaction, a self‐propagating radical cycle operates11c without the presence of an oxidant or a Ph 2 POAg complex, in contrast to previously described oxidative phosphonylation reactions 9. 24…”

Section: Methodsmentioning

confidence: 89%

Stereoselective Synthesis of Highly Functionalized Indanes and Dibenzocycloheptadienes through Complex Radical Cascade Reactions

et al. 2015

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Two highly stereoselective radical‐mediated syntheses of densely functionalized indanes and dibenzocycloheptadienes from ortho‐vinyl‐ and ortho‐vinylaryl‐substituted N‐(arylsulfonyl)‐acrylamides, respectively, are presented here. The chemoselective addition of in situ generated radicals (X.) onto the styrene moieties triggers an unprecedented reaction cascade, resulting in the formation of one new CX bond and two new CC bonds, a formal 1,4‐aryl migration, and the extrusion of SO2 to generate an amidyl radical intermediate. This intermediate, upon H abstraction, leads to the observed 5‐ and 7‐membered ring carbocyclic products, respectively, in a highly efficient manner.

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Arylphosphonylation and Arylazidation of Activated Alkenes

Cited by 67 publications

References 121 publications

Cyclic Hypervalent Iodine Reagents for Atom‐Transfer Reactions: Beyond Trifluoromethylation

Cyclic Hypervalent Iodine Reagents for Atom‐Transfer Reactions: Beyond Trifluoromethylation

Iodine(III)‐Mediated Diazidation and Azido‐oxyamination of Enamides

Stereoselective Synthesis of Highly Functionalized Indanes and Dibenzocycloheptadienes through Complex Radical Cascade Reactions

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