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

A simple N-heterocyclic carbene for the catalytic up-conversion of aldehydes into stoichiometric super electron donors DOI Creative Commons

Nadhrata Assani,

Ludivine Delfau,

Preslav Smits

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(36), P. 14699 - 14704

Published: Jan. 1, 2024

The catalytic up-conversion of aldehydes into stoichiometric super electron donors.

Language: Английский

Citations

3

On the Redox Properties of the Dimers of Thiazol-2-ylidenes That Are Relevant for Radical Catalysis DOI Creative Commons
Ludivine Delfau,

Nadhrata Assani,

Samantha Nichilo

et al.

ACS Organic & Inorganic Au, Journal Year: 2023, Volume and Issue: 3(3), P. 136 - 142

Published: March 27, 2023

We report the isolation and study of dimers stemming from popular thiazol-2-ylidene organocatalysts. The model featuring 2,6-di(isopropyl)phenyl (Dipp) N-substituents was found to be a stronger reducing agent (Eox = -0.8 V vs SCE) than bis(thiazol-2-ylidenes) previously studied in literature. In addition, remarkable potential gap between first second oxidation dimer also allows for corresponding air-persistent radical cation. latter is an unexpected efficient promoter transformation α-bromoamides into oxindoles.

Language: Английский

Citations

8

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

Metal-free reductive acyldifluoroalkylation of alkenes through cooperative NHC and organophotocatalysis DOI
Zhenhui Wang, Xiaofeng Li, Wei Li

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(17), P. 4250 - 4255

Published: Jan. 1, 2023

We introduce a reductive acyldifluoroalkylation method to synthesize β-difluoroalkyl ketones, which proceeds in metal-free manner at room temperature.

Language: Английский

Citations

6

Difluoromethylation–Carboxylation and −Deuteration of Alkenes Triggered by Electroreduction of Difluoromethyltriphenylphosphonium Bromide DOI

Fenfen Xie,

Fen Han,

Yunying Yan

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(24), P. 17134 - 17143

Published: Dec. 6, 2023

It is significant to develop novel difluoromethylation methods because of the important roles difluoromethyl groups in medicinal chemistry and material industries. Here, we developed a difluoromethylation–carboxylation difluoromethylation–deuteration method triggered by radical generated electroreduction stable easily available difluoromethyltriphenylphosphonium bromide. Various molecules containing carboxyl or deuterium can be synthesized through this method. The establishment will provide an alternative reactions.

Language: Английский

Citations

6

N-Heterocyclic Carbene and Manganese Synergistic Catalysis: A Three-Component Radical Acylmonofluoroalkylation of Alkenes DOI
Feng Liang, Ning Chen, Keguang Cheng

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(45), P. 8168 - 8172

Published: Nov. 3, 2023

Despite the importance of monofluoroalkyl groups in pharmaceutically relevant molecules, catalytic protocols for their incorporation into alkenes remain limited. We describe herein a three-component acylmonofluoroalkylation introduction such moieties through an unprecedented cooperativity between N-heterocyclic carbene catalyst and earth-abundant Mn(II) complex. This general method can be applied to variety alkenes, including styrenes, 1,3-enynes, allenes, as well complex substrates containing natural product drug motifs.

Language: Английский

Citations

5

Recent Advances in Fluoroalkylation Strategies: Exploring Novel Reactivities and Synthetic Applications of Sulfone- and Sulfinate-Based Reagents for Mono-, Di-, and Trifluoromethylations DOI
G. K. Surya Prakash, Alexander Knieb

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

Published: Sept. 5, 2024

Abstract Fluoroalkylation serves as a pivotal strategy for chemists to precisely alter the properties of small molecules. Among established fluoroalkylation protocols, sulfone and sulfinate reagents stand out versatile tools these reactions, particularly in mono-, di-, trifluoromethylations. Their versatility lies offering multiple pathways, encompassing electrophilic, nucleophilic, well radical mechanisms, thus providing diverse routes controlled molecular modifications through variety very exciting mechanistic paths. 1 Introduction 2 Monofluoromethylation Strategies 2.1 Fluorobis(phenylsulfonyl)methane (FBSM) 2.2 2-Fluoro-1,3-benzodithiole-1,1,3,3-tetraoxide (FBDT) 2.3 Benzothiazole-SO2CH2F, NaSO2CH2F, ClSO2CH2F 2.4 PhSO2CH2F 3 Difluoromethylation 3.1 PhSO2CF2H 3.2 Benzothiazole-SO2CF2H 3.3 2-PyrSO2CF2H 3.4 NaSO2CF2H 4 Trifluoromethylation 4.1 PhSO2CF3 4.2 2-PyrSO2CF3 4.3 Benzothiazole-SO2CF3 4.4 NaSO2CF3 4.4.1 Electrochemical Approaches 4.4.2 Photochemical 4.4.3 Other Noteworthy 5 Conclusion

Language: Английский

Citations

1

Carbene-catalyzed [3 + 2 + 1] annulation via C–N radical coupling of iminyl radicals and ketyl radicals DOI

Wenchang Li,

Peng Zhou, Qing Zhao

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(18), P. 3784 - 3788

Published: Jan. 1, 2023

An NHC-catalyzed [3 + 2 1] annulation of vinyl azides, aldehydes, and Togni’s reagents was reported. The cascade involves SET redox transformation, denitrogenated radical migration, C–N coupling, defluorinated cyclization.

Language: Английский

Citations

1

Synthesis of Difluoromethylated Alkenes via Copper‐Catalyzed Protodefluorination of β‐(Trifluoromethyl)styrenes DOI Creative Commons
Tao Dong, Yibin Ye, Yanhui Wang

et al.

Chemistry - An Asian Journal, Journal Year: 2023, Volume and Issue: 18(19)

Published: Aug. 18, 2023

Abstract Under typical copper‐catalyzed hydroboration conditions, β ‐(trifluoromethyl)styrenes demonstrate unusal reactivities by forming difluoromethylated alkenes via a net protodefluorination process. This is also distinct from trifluoromethyl with alkyl substituents where defluoroborylation products predominate.

Language: Английский

Citations

1

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

Citations

0