Photocatalyzed dehalogenative deuteration with silacarboxylic acids as halogen-atom transfer agents

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(17), С. 4757 - 4761

Опубликована: Янв. 1, 2024

A visible light-induced organophotocatalytic strategy for dehalogenative deuteration of a wide variety primary, secondary, and tertiary alkyl bromides is reported.

Язык: Английский

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Recent Advances in the Application of Carbon Dioxide Radical Anion

Chinese Journal of Organic Chemistry, Год журнала: 2024, Номер 44(10), С. 3117 - 3117

Опубликована: Янв. 1, 2024

Язык: Английский

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Combined Photocatalysis and Lewis Acid Catalysis Strategy for the Oxa-Pictet–Spengler Reactions of Ethers

ACS Catalysis, Год журнала: 2024, Номер 14(10), С. 7949 - 7955

Опубликована: Май 7, 2024

Saturated oxygen-containing heterocycles are present in numerous natural products and biologically active compounds. While the oxa-Pictet–Spengler reaction conventionally serves as a traditional synthetic strategy for preparing arene-fused tetrahydropyrans (THPs), existing methods typically involve harsh conditions. Disclosed herein is development of mild photocatalytically triggered ethers providing approach to fused THP The tuned dual photo/hydrogen-atom transfer (HAT) catalysis enables site- chemoselective C–H functionalization at benzylic ether, which results formation benzoate acetal intermediate. key intermediate then exposed subsequent Lewis acid catalysis, thus facilitating oxocarbenium ion generation ring closure. Notably, this combination successfully addresses concerns related overoxidation inherent photocatalytic systems.

Язык: Английский

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Photoredox Activation of Fluorinated Organozinc Reagents: Hydrofluoroalkylation of Unactivated and Electron Deficient Alkenes

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(16), С. 11826 - 11835

Опубликована: Июль 26, 2024

Hydrofluoroalkylation of alkenes with organozinc reagents under photocatalytic conditions is described. The fluorinated alkyl radicals were generated from organozincs by the single electron oxidation carbon-zinc bond. radical addition step followed either hydrogen atom transfer for unactivated olefins or a reduction/protonation sequence strongly accepting arylidenemalononitriles.

Язык: Английский

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Building Catalytic Reactions One Electron at a Time

Accounts of Chemical Research, Год журнала: 2024, Номер unknown

Опубликована: Сен. 24, 2024

ConspectusClassical education in organic chemistry and catalysis, not the least my own, has centered on two-electron transformations, from nucleophilic attack to oxidative addition. The focus is well-founded, as this brand of enabled incredible feats synthesis, development life-saving pharmaceuticals production ubiquitous commodity chemicals. With that said, approach many ways complementary nature, where enzymes frequently make use single-electron "radical" steps achieve challenging reactions with exceptional selectivity, including light detection C-H hydroxylation. While power radical elementary undeniable, fundamental understanding of─and ability apply─these catalysis remains underdeveloped, constraining palette which chemists can new reactions.Motivation remedy traditional underemphasis been intensified by runaway success outer-sphere photoredox only confirming versatility radicals anthropogenic but also teaching value robust well-understood catalytic cycles for reaction design. Indeed, I would argue fueled strong its underlying steps, consideration transfer (SET) energetics allowing be designed

Язык: Английский

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Photoredox/HAT-Catalyzed Intramolecular Hydrocyclization of Alkenes toward 2,3-Fused Quinazolinones and Dihydroquinazolinones

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Окт. 2, 2024

New photochemical approaches to 2,3-fused quinazolinones and dihydroquinazolinones are disclosed. The intramolecular hydrocyclization proceeds in moderate excellent yields across diverse alkenes with high regioselectivity diastereocontrol. Mechanistic studies indicated that the radical cascade processes involve thiophenol acting as single-electron transfer hydrogen atom reagents. success of gram-scale synthesis proves strategy can be used for practical applications.

Язык: Английский

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Visible Light Mediated Difluoroalkylation of Alkenes Using Mercaptobenzothiazole‐Derived Sulfide Reagent

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(24), С. 5171 - 5175

Опубликована: Авг. 29, 2024

Abstract A method for the reductive difluoromethylation of alkenes with 2‐difluoromethylthio(benzothiazole) under photocatalytic conditions is described. The reaction involves generation difluoromethyl radical by means trimethyltriazinane, which serves as a precursor strongly reducing cyclic diaminoalkyl radical.

Язык: Английский

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Functionalization of Boranes through Thiol/Oxygen Catalysis^†

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(22), С. 2804 - 2810

Опубликована: Июль 17, 2024

Comprehensive Summary A greener and more convenient alternative to traditional methods for the generation of thiyl radical as hydrogen atom transfer (HAT) catalyst is developed, using molecular oxygen oxidize thiol without need chemical initiators or light irradiation. The thiol/oxygen catalysis enables selective efficient difunctionalization borane.

Язык: Английский

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