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Book Sections Year : 2023

Oxidation : C–X Bond Formation (X=Halogen, S, Se)

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Abstract

The field of enantioselective C-X bond formation (X = halogen, S, Se) has grown steadily over the past decade. It is particularly true of electrophilic enantioselective fluorination owing to the beneficial effects of fluorination for tuning the biological activity of drug candidates. Other halogenations (X = Cl, Br) remain less developed. Other oxidations of C-H bonds include the sulfenylation, especially the trifluoromethylthiolation, and the selenenylation. Outstanding results are presented on the direct enantioselective C-X bond formation via C-H functionalization by means of electrophilic reagents and powerful asymmetric synthesis methodologies. Key points: • The enantioselective electrophilic fluorination with the aid of chiral fluorinating agents, by means of organocatalysis including phase-transfer catalysis, and by means of transitionmetal catalysis is presented. • Analogous chlorination and bromination exploiting asymmetric synthesis methodologies complement the C-Hal bond formations. • The enantioselective electrophilic sulfenylation and selenenylation are also presented.
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Dates and versions

hal-03858965 , version 1 (24-11-2022)

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  • HAL Id : hal-03858965 , version 1

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Samir Bouzbouz, Dominique Cahard. Oxidation : C–X Bond Formation (X=Halogen, S, Se). Hisashi Yamamoto; Erick Carreira. Comprehensive Chirality, In press. ⟨hal-03858965⟩
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