Recent advances in selective mono-/dichalcogenation and exclusive dichalcogenation of C(sp²)–H and C(sp³)–H bonds

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 22(4), С. 645 - 681

Опубликована: Дек. 23, 2023

Organochalcogen compounds are prevalent in numerous natural products, pharmaceuticals, agrochemicals, polymers, biological molecules and synthetic intermediates. Direct chalcogenation of C-H bonds has evolved as a step- atom-economical method for the synthesis chalcogen-bearing compounds. Nevertheless, direct severely lags behind C-C, C-N C-O bond formations. Moreover, compared with monochalcogenation, reports selective mono-/dichalcogenation exclusive dichalcogenation relatively scarce. The past decade witnessed significant advancements various C(sp

Язык: Английский

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Iron-Catalyzed Friedel–Crafts-type 3,5-Diacylation of Indoles

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(14), С. 10272 - 10282

Опубликована: Июль 5, 2024

The exploration of remote functionalization indoles is impeded by the inherently dominant reactivity intrinsic to pyrrole moiety. Herein, we delineate a novel strategy facilitated Lewis acid mediation, enabling C-H functionalization, which culminates in synthesis an array selectively functionalized indole derivatives, encompassing 3-trifluoroacetyl and 5-benzoyl motifs, utilizing trifluoroacetic anhydride various acyl chlorides. Notably, protocol exhibits versatility, as epitomized extension C5-acylation alkylation sulfonation reactions. This methodology distinguished its exemplary regio- chemo-selectivity, extensive substrate scope, commendable tolerance diverse functional groups, employment comparatively mild reaction conditions.

Язык: Английский

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Synthesis of 2,3‐Diaminoindolesvia a Copper‐Iodine Co‐catalytic Strategy

Chinese Journal of Chemistry, Год журнала: 2023, Номер 41(24), С. 3567 - 3572

Опубликована: Авг. 28, 2023

Comprehensive Summary A one‐pot synthesis of vicinal diamines using indoles, azoles and phenothiazines in a tandem multi‐component reaction is developed. The utilization copper‐iodine co‐catalytic system enables the generation diverse range diaminoindoles with good selectivity moderate to yields. An attractive aspect this method that it can be conducted under mild environmentally friendly conditions, showcasing its potential as an alternative approach for synthesizing diamines. Moreover, use multicomponent highlights power versatility such strategies synthetic chemistry.

Язык: Английский

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Organoselenium-Catalyzed C2,3-Diarylation of N–H Indoles

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(10), С. 7216 - 7224

Опубликована: Май 2, 2024

An organoselenium-catalyzed C2,3-diarylation of unprotected N–H indoles with electron-rich aromatics has been developed. This one-pot multicomponent tandem cross-dehydrogenation coupling reaction allows for the incorporation two different aromatic groups to indoles. More importantly, this approach offers significant advantages, including a high atom and step economy, eliminating need prepreparation substrates, streamlining synthetic process enhancing its practicality. Overall, presents an efficient versatile strategy functionalization indole derivatives.

Язык: Английский

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Directing-group-free strategy for the iodine-mediated regioselective dichalcogenation of indolines: understanding the full catalytic cycles

Organic Chemistry Frontiers, Год журнала: 2023, Номер 11(3), С. 871 - 884

Опубликована: Дек. 11, 2023

A metal-free catalytic method for the regioselective direct dehydrogenation–dichalcogenation of indolines. The reaction mechanism and regioselectivity have been elucidated via density functional theory studies.

Язык: Английский

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Five-membered ring systems: Pyrroles and benzo analogs

Progress in heterocyclic chemistry, Год журнала: 2024, Номер unknown, С. 123 - 173

Опубликована: Янв. 1, 2024

Язык: Английский

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