Enantioselective Hydroazidation of Trisubstituted Non‐Activated Alkenes

Meyer, Daniel; Renaud, Philippe

doi:10.1002/ange.201703340

Cited by 11 publications

(1 citation statement)

References 66 publications

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“…4b ). Finally, based on our recent work on the enantioselective hydroazidation 44 , a one-pot enantioselective hydrofluorination of 1b was performed (Fig. 4c ).…”

Section: Resultsmentioning

confidence: 99%

A third generation of radical fluorinating agents based on N-fluoro-N-arylsulfonamides

et al. 2018

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Radical fluorination has been known for a long time, but synthetic applications were severely limited by the hazardous nature of the first generation of reagents such as F2 and the strongly electrophilic nature of the second generation of reagents such as N-fluorobenzenesulfonimide (NFSI) and Selecfluor®. Here, we report the preparation, use and properties of N-fluoro-N-arylsulfonamides (NFASs), a class of fluorinating reagents suitable for radical fluorination under mild conditions. Their N–F bond dissociation energies (BDE) are 30–45 kJ mol−1 lower than the N–F BDE of the reagents of the second generation. This favors clean radical fluorination processes over undesired side reactions. The utility of NFASs is demonstrated by a metal-free radical hydrofluorination of alkenes including an efficient remote C–H fluorination via a 1,5-hydrogen atom transfer. NFASs have the potential to become the reagents of choice in many radical fluorination processes.

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“…4b ). Finally, based on our recent work on the enantioselective hydroazidation 44 , a one-pot enantioselective hydrofluorination of 1b was performed (Fig. 4c ).…”

Section: Resultsmentioning

confidence: 99%

A third generation of radical fluorinating agents based on N-fluoro-N-arylsulfonamides

et al. 2018

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Boron‐Mediated Radical Reactions

André‐Joyaux¹,

Gnägi²,

Gnägi‐Lux³

et al. 2022

Patai's Chemistry of Functional Groups

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This chapter focuses on the use of boron‐containing reagents in radical reactions. In all reactions presented here, boron is playing a key role in the radical process either by being part of the radical process or by influencing the reactivity of the radical and nonradical species. The diversity of radical chemistry involving organoboron species is spectacular. They represent a unique source of radicals for chain reactions allowing for instance efficient radical initiation at low temperature and generation of a broad range of functionalized alkyl radicals from easily prepared organoboranes. Recent developments in redox chemistry including photoredox catalysis, electrochemistry, and single‐electron‐transfer processes have allowed the generation of alkyl and aryl radicals from stable organoboron derivatives such as alkyl‐ and aryl‐trifluoroborates. A broad range of synthetic applications such as radical cascade processes, multicomponent reactions, and cross‐coupling reactions in the presence of suitable metals are possible. Besides radical generation, boron‐containing radical precursors and radical traps are becoming of increasing importance to prepare building blocks enclosing a boron moiety suitable for further functionalization. Merging radical processes with classical boron chemistry including Suzuki–Miyaura‐type cross‐coupling processes; homologation via 1,2‐metallate rearrangement; and conversions to alcohols, amines, and related compounds offers unique opportunities for applications in organic synthesis.

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