Iron‐Catalyzed Ring‐Opening/Allylation of Cycloalkyl Hydroperoxides with Allylic Sulfones DOI

Ming‐Hua Wang,

Jingqi Tao, Fan Yang

et al.

Asian Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 11(2)

Published: Jan. 21, 2022

Abstract An efficient iron‐catalyzed allylation of cycloalkyl hydroperoxides with allylic sulfones via C−C bond cleavage is presented. This protocol provides an approach to a wide range distally allylated ketones good functional group tolerance and high regioselectivity under redox‐neutral conditions. Preliminary mechanistic study implies radical process might be involved in this reaction.

Language: Английский

Metal-catalyzed asymmetric reactions enabled by organic peroxides DOI

Nengbo Zhu,

Huijie Yao,

Xiyu Zhang

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(5), P. 2326 - 2349

Published: Jan. 1, 2024

This review summarizes the advances in metal-catalyzed asymmetric reactions enabled by organic peroxides that have been found to exhibit multifunctionalities, for instance, applied as stoichiometric reactants, reagents, or catalytic amount reagents.

Language: Английский

Citations

19

Emerging Trends in Copper-Promoted Radical-Involved C–O Bond Formations DOI

Peng‐Zi Wang,

Jia‐Rong Chen, Wen‐Jing Xiao

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(32), P. 17527 - 17550

Published: Aug. 2, 2023

The C–O bond is ubiquitous in biologically active molecules, pharmaceutical agents, and functional materials, thereby making it an important group. Consequently, the development of bond-forming reactions using catalytic strategies has become increasingly research topic organic synthesis because more conventional methods involving strong base acid have many limitations. In contrast to ionic-pathway-based methods, copper-promoted radical-mediated formation experiencing a surge interest owing renaissance free-radical chemistry photoredox catalysis. This Perspective highlights appraises state-of-the-art techniques this burgeoning field. contents are organized according different reaction types working models.

Language: Английский

Citations

43

When all C–C breaks LO–Ose DOI Creative Commons

Jeremy H. Dworkin,

Brady W. Dehnert,

Ohyun Kwon

et al.

Trends in Chemistry, Journal Year: 2023, Volume and Issue: 5(3), P. 174 - 200

Published: Feb. 14, 2023

Organic peroxides are becoming popular intermediates for novel chemical transformations. The weak O-O bond is readily reduced by transition metals, including iron and copper, to initiate a radical cascade process that breaks C-C bonds. Great potential exists the rapid generation of complexity, originating from ability couple resulting free radicals with wide range partners. First, this review article discusses history synthesis organic peroxides, providing context necessary understand methodology. Then, it highlights 91 examples recent applications functionalization bonds accessed through metal-mediated reduction peroxides. Finally, we provide some comments about safety when working

Language: Английский

Citations

18

Synthetic utility of functionalized alkylsilyl peroxides for Fe-catalyzed and visible-light-promoted radical transformation DOI Creative Commons
Jiahao Liu,

Shiyong Liu,

Zhe Wang

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(13), P. 4757 - 4762

Published: Jan. 1, 2024

α-Keto-, β-acetoxy- and β-amidoalkylsilyl peroxides are prepared from various precursors utilized for Fe-catalyzed visible-light-promoted radical functionalization with coupling partners under mild conditions a broad substrate scope.

Language: Английский

Citations

4

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

9

The alkylation of phenol with methanol: Conversion of anisole and two-step reaction process on X zeolites DOI
Lei Li, Xianlong Gao, Fangtao Huang

et al.

Applied Catalysis A General, Journal Year: 2025, Volume and Issue: unknown, P. 120168 - 120168

Published: Feb. 1, 2025

Language: Английский

Citations

0

Copper-catalyzed radical ring-opening halogenation with HX DOI
Shuai Liu, Ming Bai, Peng‐Fei Xu

et al.

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(69), P. 8652 - 8655

Published: Jan. 1, 2021

An efficient copper-catalyzed radical ring-opening halogenation with HX (aq) is described. This protocol provides a practical access to distally chlorinated, brominated and iodinated alkyl ketones nitriles moderate good yields.

Language: Английский

Citations

17

Ni-Catalyzed C(sp2)–H alkylation of N-quinolylbenzamides using alkylsilyl peroxides as structurally diverse alkyl sources DOI

Saori Tsuzuki,

Shunya Sakurai, Akira Matsumoto

et al.

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(64), P. 7942 - 7945

Published: Jan. 1, 2021

A Ni-catalyzed direct C–H alkylation of N-quinolylbenzamides using alkylsilyl peroxides as alkyl-radical precursors is described.

Language: Английский

Citations

16

Iron-Catalyzed Thiolation and Selenylation of Cycloalkyl Hydroperoxides via C–C Bond Cleavage DOI

Qing-Xin Sun,

He Chen, Shuai Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(17), P. 11987 - 11997

Published: Aug. 10, 2021

A cheap iron-catalyzed C–C bond cleavage/thiolation and selenylation of cycloalkyl hydroperoxides are presented. This redox-neutral protocol provides efficient access to diverse distal keto-functionalized thioethers selenium compounds. Remarkably, only some amounts disulfides required for this transformation.

Language: Английский

Citations

15

A new approach for the copper-catalyzed functionalization of alkyl hydroperoxides with organosilicon compounds via in-situ-generated alkylsilyl peroxides DOI

Wenfeng Zhong,

Weiping Xu,

Qin Yang

et al.

Tetrahedron, Journal Year: 2022, Volume and Issue: 112, P. 132627 - 132627

Published: Jan. 8, 2022

Language: Английский

Citations

11