Recent advances in transition-metal-free conversion of aldehydes to ketones DOI Creative Commons

Yike Bai,

Wenhua Yu,

Rong Chen

et al.

Green Synthesis and Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: May 1, 2024

The preparation of functionalized ketones occupies an important position in synthetic organic chemistry because are ubiquitous structural motifs a broad range compounds with various applications. conversion aldehydes to is one the most convenient and straightforward routes, which has been extensively studied field transition metal catalysis. In comparison, transition-metal-free remains underdeveloped. last decade, emergence new advances upgraded toolbox for ketone synthesis from absence metals. this review, we have mainly summarized three types reactions enabling ketones, emphasis on those involving main group element

Language: Английский

Photoinduced C–H heteroarylation of enamines via quadruple cleavage of CF2Br2 DOI

Wanqing Zuo,

Lingling Zuo,

Xiao Geng

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(24), P. 6112 - 6116

Published: Jan. 1, 2023

The C–H functionalization of enamines has attracted much attention over the past few years; however, heteroarylation still remains rare.

Language: Английский

Citations

69

Radical-Polar Crossover Enabled Triple Cleavage of CF2Br2: A Multicomponent Tandem Cyclization to 3-Fluoropyrazoles DOI

Wanqing Zuo,

Lingling Zuo,

Xiao Geng

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(32), P. 6062 - 6066

Published: Aug. 8, 2023

The elaboration of step-economy and catalytic approaches for accessing diverse fluorinated heterocyclics is highly desirable. Described herein a radical-polar crossover enabled three-component cyclization to polysubstituted fluoropyrazoles by using CF2Br2 as novel C1F1 synthon. Mechanistic experiments revealed that the in situ generation reactive intermediate gem-difluorovinylimine ion key this transformation. This protocol unlocks reactivity adds significant synthetic values fluorine chemistry.

Language: Английский

Citations

64

Recent advances in N-heterocyclic carbene (NHC)-catalyzed fluorination and fluoroalkylation DOI

Zefeng Jin,

Fuxiang Zhang, Xiao Xiao

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(7), P. 2112 - 2133

Published: Jan. 1, 2024

Organofluorine compounds are of high value. NHC-catalyzed fluorination and fluoroalkylation have served as powerful versatile vehicles for accessing the related organofluorines. This review focuses on recent developments in this area.

Language: Английский

Citations

25

Cooperative Carbene Photocatalysis for β-Amino Ester Synthesis DOI
Nao Tanaka, Joshua L. Zhu,

Oniya L. Valencia

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: unknown

Published: Oct. 31, 2023

β-Amino acids are useful building blocks of bioactive molecules, including peptidomimetics and pharmaceutical compounds. The current limited accessibility to β2,2-type amino which bear an α-quaternary center has their use in chemical synthesis biological investigations. Disclosed herein is the development a new N-heterocyclic carbene/photocatalyzed aminocarboxylation olefins, affording β2,2-amino esters with high regioselectivity. generation nitrogen-centered radicals derived from simple imides via sequence deprotonation single-electron oxidation allows for subsequent addition geminal-disubstituted olefins regioselectively. intermediate tertiary then cross-couple stabilized azolium-based radical generated situ efficiently construct quaternary centers. Mechanistic studies, Stern–Volmer fluorescence quenching experiments, support proposed catalytic cycle.

Language: Английский

Citations

18

Radical Acylation of Alkenes by NHC‐Organocatalysis DOI Open Access
Qian Tang, Ding Du, Jian Gao

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(48)

Published: Oct. 11, 2023

Abstract N ‐Heterocyclic carbene (NHC) catalyzed radical‐radical reactions have been proven to be powerful strategies for assembling ketyl‐containing compounds via single electron transfer (SET) pathway under either thermal conditions or photoredox conditions. In this context, acylation of alkenes radical relay NHC‐organocatalysis has also opened a new window the difunctionalization construct valuable molecules in organic synthesis. review, advances and progress were summarized according different ways generation key NHC‐bound ketyl‐type radicals. Furthermore, reaction scopes, limitations mechanisms discussed based on types catalytic systems. Conclusions perspectives put forward at end.

Language: Английский

Citations

17

Acylmonofluoromethylation of alkenes via dual NHC/photoredox catalysis DOI
Shichao Tian, Mingxi Chen, Yihan Tang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(24), P. 6124 - 6130

Published: Jan. 1, 2023

We herein describe a three-component radical acylmonofluoromethylation of alkenes by cooperative NHC/photoredox catalysis to synthesize various monofluorinated alkyl aryl ketones.

Language: Английский

Citations

11

Palladium-catalyzed cross-coupling of gem-difluorocyclopropanes with gem-diborylalkanes: facile synthesis of a diverse array of gem-diboryl-substituted fluorinated alkenes DOI Creative Commons
Ebrahim‐Alkhalil M. A. Ahmed, Hongchen Zhang,

Wen-Gen Cao

et al.

RSC Advances, Journal Year: 2025, Volume and Issue: 15(13), P. 10265 - 10272

Published: Jan. 1, 2025

This study introduces an efficacious palladium-catalyzed method for the regioselective and stereoselective cross-coupling of gem -difluorinated cyclopropanes with array -diborylalkanes under mild reaction conditions.

Language: Английский

Citations

0

Aminoacylation of Alkenes by Cooperative NHC and Photoredox Catalysis DOI
Lena Lezius,

Jannik Reimler,

Armido Studer

et al.

Synlett, Journal Year: 2023, Volume and Issue: 35(04), P. 445 - 450

Published: Aug. 1, 2023

Abstract Cooperative NHC and photoredox catalysis has gained significant attention as an emerging research field in recent years. Herein, we report a cyclizing aminoacylation of alkenes, which is enabled through the combination these two catalytic modes. The key step radical/radical cross-coupling between persistent ketyl radical transient benzylic or aliphatic C-radical, generated cyclization oxidatively formed amidyl radical. Several carbamates, amides sulfonamides containing alkene moiety different acyl fluorides can be used substrates. resulting products are obtained moderate to good yields.

Language: Английский

Citations

8

NHC-catalyzed radical acylation of cycloalkyl silyl peroxides to access 1,6-,1,7-, and 1,8-diketones DOI
Chaolei Liu, Jingyi Wang, Xinlong Liu

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(88), P. 13175 - 13178

Published: Jan. 1, 2023

An NHC organocatalytic radical acylation of cycloalkyl silyl peroxides with aldehydes was developed for the efficient and rapid synthesis long-chain 1,6-/1,7-/1,8-diketones, especially unsymmetrical ones.

Language: Английский

Citations

7

Recent progress in carbene-catalyzed fluoroalkylation DOI
Bei Zhang, Xuan Zhang, Jian Wang

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: 67(8), P. 2448 - 2460

Published: June 26, 2024

Language: Английский

Citations

2