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

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

26

Recent advances in three-component radical acylative difunctionalization of unsaturated carbon–carbon bonds DOI
Jiaqiong Sun, Lihong V. Wang, Guangfan Zheng

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(18), P. 4488 - 4515

Published: Jan. 1, 2023

This review highlights the recent advances in radical acylated difunctionalization of unsaturated carbon–carbon bonds and focuses on mechanistic insights these transformations.

Language: Английский

Citations

31

N-monofluoromethoxy benzoimidazole: a bench stable reagent for direct radical monofluoromethoxylation of alkenes DOI
Ning Chen, Jingjing Ling, Keguang Cheng

et al.

Science China Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 12, 2025

Language: Английский

Citations

1

Radical acylation: concepts, synthetic applications and directions DOI
Yue Zhang, Yili Zhang, Jian Lin

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(4), P. 1056 - 1085

Published: Jan. 1, 2023

In this tutorial, reaction scopes, limitations and mechanisms of radical acylations are summarized discussed according to types catalytic systems.

Language: Английский

Citations

21

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

Copper-Catalyzed Visible-Light-Induced Allylic Difluoromethylation of Unactivated Alkenes Using Difluoroacetic Acid DOI

Jinlian Wang,

Ziwei Luo,

Yili Wu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(6), P. 1045 - 1049

Published: Feb. 8, 2023

We herein describe a straightforward allylic difluoromethylation reaction of unactivated alkenes. Compared to cross-couplings prefunctionalized substrates for the construction CF2H bonds, this employs readily available alkenes as under mild conditions. Difluoroacetic acid is used an inexpensive and easy-to-handle source radical visible light irradiation with PIDA. The copper catalyst plays important role diverting pathway toward opposed previously found hydrodifluoromethylation.

Language: Английский

Citations

13

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

NHC and photoredox catalysis dual-catalyzed 1,4-mono-/di-fluoromethylative acylation of 1,3-enynes DOI

Jiuli Xia,

Ruiyang Ma,

Lihong V. Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(11), P. 3089 - 3099

Published: Jan. 1, 2024

NHC and photocatalysis dual-catalyzed mono/difluoromethylative acylation of 1,3-enynes was realized, providing fluormethyl-substituted allenyl ketones. SO 2 might play a critical role in achieving high reactivity selectivity.

Language: Английский

Citations

4

1,2-Aminoalkylacylation of styrenes by cooperative NHC/photoredox dual catalysis DOI
Lili Wu, Chengming Wang

Synthetic Communications, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 9

Published: April 3, 2025

Language: Английский

Citations

0

Radical Acylfluoroalkylation of 1,3-Enynes via N-Heterocyclic Carbene/Photoredox Cooperative Catalysis DOI
Shichao Tian, Ning Chen, Keguang Cheng

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(20), P. 4351 - 4355

Published: May 10, 2024

We report a novel three-component radical acylfluoroalkylation of 1,3-enynes by synergistic N-heterocyclic carbene (NHC)/photoredox catalysis toward various fluorinated allenic aryl ketones. This protocol features broad substrate scope and excellent functional group tolerability, with examples late-stage modification drug molecules natural products. Notably, seven different fluoroalkyl motifs can be introduced to 1,3-enynes, further demonstrating the robustness generality this method. The generation from each sulfinate reagent was individually supported EPR experiments.

Language: Английский

Citations

3