Photocatalytic Enantioselective Hydrosulfonylation of α,β‐Unsaturated Carbonyls with Sulfonyl Chlorides

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(46)

Опубликована: Окт. 2, 2023

This research explores the enantioselective hydrosulfonylation of various α,β-unsaturated carbonyl compounds via use visible light and redox-active chiral Ni-catalysis, facilitating synthesis enantioenriched α-chiral sulfones with remarkable enantioselectivity (exceeding 99 % ee). A significant challenge entails enhancing reactivity between metal-coordinated moderate electrophilic sulfonyl radicals, aiming to minimize background reactions. The success our approach stems from two distinctive attributes: 1) Cl-atom abstraction employed for radical generation chlorides, 2) single-electron reduction produce a key enolate Ni-complex. latter process appears enhance feasibility radical's addition electron-rich radical. An in-depth investigation into reaction mechanism, supported by both experimental observations theoretical analysis, offers insight intricate process. Moreover, versatility methodology is highlighted through its successful application in late-stage functionalization complex bioactive molecules, demonstrating practicality as strategy producing sulfones.

Язык: Английский

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Metal-free photosensitized aminosulfonylation of alkenes: a practical approach to β-amido sulfones

Green Chemistry, Год журнала: 2023, Номер 25(10), С. 3857 - 3863

Опубликована: Янв. 1, 2023

A general and environmentally friendly organic photo-induced strategy was developed for the synthesis of diverse alkyl-substituted β-amino sulfone derivatives, including primary, secondary, tertiary products.

Язык: Английский

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Visible Light‐Mediated Cobalt and Photoredox Dual‐Catalyzed Asymmetric Reductive Coupling for Axially Chiral Secondary Alcohols^†

Chinese Journal of Chemistry, Год журнала: 2023, Номер 41(23), С. 3253 - 3260

Опубликована: Июль 20, 2023

Comprehensive Summary Secondary alcohols bearing both axial and central chirality comprise attractive biological activity exhibit excellent chiral induction in asymmetric reactions. However, only very limited catalytic approaches were developed for their synthesis. We herein describe visible light‐mediated cobalt‐catalyzed reductive Grignard‐type addition of aryl iodides with axially prochiral biaryl dialdehydes leading to the direct construction secondary alcohols. Preliminary mechanistic studies indicate that efficient kinetic recognition diastereomers might occur improve stereoselectivity, which open a new avenue challenging cascade multiple elements. This protocol features enantio‐ diastereoselectivity, green mild conditions, simple operation, broad substrate scope, providing modular platform synthesis

Язык: Английский

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Applications of Hantzsch Esters in Organocatalytic Enantioselective Synthesis

Catalysts, Год журнала: 2023, Номер 13(2), С. 419 - 419

Опубликована: Фев. 16, 2023

Hantzsch esters (1,4-dihydropyridine dicarboxylates) have become, in this century, very versatile reagents for enantioselective organic transformations. They can act as hydride transfer agents to reduce, regioselectively, a variety of multiple bonds, e.g., C=C and C=N, under mild reaction conditions. are excellent the dearomatization heteroaromatic substances, participate readily cascade processes. In last few years, they also become useful photoredox reactions. sacrificial electron hydrogen donors when 4-alkyl or 4-acyl-substituted, alkyl acyl radical agents. These reactions may take place presence absence photocatalyst. This review surveys literature published area five years.

Язык: Английский

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Metal-free synthesis of sulfonylated indolo[2,1-a]isoquinolines from sulfur dioxide

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(13), С. 3521 - 3526

Опубликована: Янв. 1, 2022

Access to sulfonylated indolo[2,1- a ]isoquinolines through an efficient three-component reaction of 2-aryl- N -acryloyl indoles, sulfur dioxide and aryldiazonium tetrafluoroborates is developed.

Язык: Английский

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