A photoredox catalyzed iminyl radical-triggered C–C bond cleavage/addition/Kornblum oxidation cascade of oxime esters and styrenes: synthesis of ketonitriles

Chemical Communications, Год журнала: 2018, Номер 54(86), С. 12262 - 12265

Опубликована: Янв. 1, 2018

A photoredox-catalyzed iminyl radical-triggered C-C bond cleavage/addition/Kornblum oxidation cascade of cycloketone oxime esters and styrenes in DMSO is described. This three-component, one-pot procedure features mild conditions, a broad substrate scope, high functional group tolerance, providing an efficient approach to access diversely functionalized ketonitriles.

Язык: Английский

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Photocatalytic C–C Bond Activation of Oxime Ester for Acyl Radical Generation and Application

Organic Letters, Год журнала: 2019, Номер 21(11), С. 4153 - 4158

Опубликована: Май 28, 2019

A unified strategy to generate acyl radical from oxime ester via selective C-C bond activation is reported. Under visible-light irradiation, single-electron transfer fac-Ir(ppy)3 related takes place followed by a fast β-fragment of yield aryl and aliphatic radicals, subsequently captured diverse Michael acceptors. More interestingly, the enables coupling with energy excited enone intermediate formed in situ for cyclobutane formation.

Язык: Английский

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Practical, metal-free remote heteroarylation of amides via unactivated C(sp³)–H bond functionalization

Chemical Science, Год журнала: 2019, Номер 10(28), С. 6915 - 6919

Опубликована: Янв. 1, 2019

A simple and practical approach for the regioselective heteroarylation of amides via unactivated C(sp³)–H bond functionalization is described.

Язык: Английский

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Functionalization of remote C(sp3)-H bonds enabled by copper-catalyzed coupling of O-acyloximes with terminal alkynes

Nature Communications, Год журнала: 2020, Номер 11(1)

Опубликована: Янв. 21, 2020

Abstract Transition metal catalyzed Sonogashira cross-coupling of terminal alkynes with aryl(vinyl) (pseudo)halides has been successfully extended to alkyl halides for the synthesis functionalized internal alkynes. The direct alkynylation remote unfunctionalized sp 3 carbon by remains difficult realize. We report herein an approach this synthetic challenge developing two catalytic protocols. In presence a amount Cu(I) salt and tridentate ligand ( t Bu -terpyridine), O -acyloximes derived from cycloalkanones acyclic ketones are efficiently coupled afford variety γ- δ-alkynyl nitriles γ-alkynyl ketones, respectively. These reactions proceed through domino sequence involving copper-catalyzed reductive generation iminyl radical followed translocation via either β-scission or 1,5-hydrogen atom transfer (1,5-HAT) resulting translocated radicals. protocols applicable complex natural products.

Язык: Английский

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Iminyl Radical-Triggered Intermolecular Distal C(sp³)–H Heteroarylation via 1,5-Hydrogen-Atom Transfer (HAT) Cascade

Organic Letters, Год журнала: 2019, Номер 21(4), С. 917 - 920

Опубликована: Янв. 28, 2019

An efficient iron-catalyzed intermolecular remote C(sp3)–H heteroarylation of alkyl ketones has been developed via an iminyl radical-triggered 1,5-hydrogen-atom transfer (HAT) cascade. This protocol was amenable to a wide variety and heteroaryls, thus providing straightforward method for the late-stage functionalization alkylketones heteroaryls.

Язык: Английский

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