Photoinduced Ligand-to-Copper Charge Transfer for Aryl Decarboxylative Allylation, Thiolation, and Bromination DOI

Ao-Men Hu,

Jia‐Lin Tu,

Ke Wang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 27, 2024

Herein, aryl decarboxylative allylation, thiolation, and bromination reactions via photoinduced ligand-to-copper charge transfer are described. Utilizing inexpensive copper metal, the transformations of various carboxylic acids enable rapid synthesis corresponding alkene, thioether, bromide derivatives under visible light irradiation, which offers significant synthetic value. The reaction conditions mild straightforward, exhibiting a broad substrate compatibility. Furthermore, this method can be applied for late-stage modification complex drug molecules.

Language: Английский

Iron-catalyzed fluoroalkylative alkylsulfonylation of alkenes via radical-anion relay DOI Creative Commons
Xiaoya Hou, Hongchi Liu, Hanmin Huang

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Feb. 17, 2024

Abstract Transition metal-catalyzed reductive difunctionalization of alkenes with alkyl halides is a powerful method for upgrading commodity chemicals into densely functionalized molecules. However, super stoichiometric amounts metal reductant and the requirement installing directing group to suppress inherent β-H elimination bring great limitations this type reaction. We demonstrate herein that two different accessible via radical-anion relay Na 2 S O 4 as both sulfone-source. The together electron-shuttle catalyst crucial divert mechanistic pathway toward formation sulfone anion instead previously reported alkylmetal intermediates. Mechanistic studies allow identification carbon-centered radical sulfur-centered radical, which are in equilibrium capture or extrusion SO could be converted accelerated by iron catalysis, leading observed high chemoselectivity.

Language: Английский

Citations

24

Construction of C−S and C−Se Bonds from Unstrained Ketone Precursors under Photoredox Catalysis DOI Creative Commons
Hao Wu, Shuguang Chen,

Chunni Liu

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(8)

Published: Jan. 8, 2024

A mild photoredox catalyzed construction of sulfides, disulfides, selenides, sulfoxides and sulfones from unstrained ketone precursors is introduced. Combination this deacylative process with S

Language: Английский

Citations

23

Radical-Mediated Decarboxylative C–C and C–S Couplings of Carboxylic Acids via Iron Photocatalysis DOI
Lijing Li, Wei Yi,

Yulian Zhao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(5), P. 1110 - 1115

Published: Jan. 26, 2024

Despite the significant success of decarboxylative radical reactions, catalytic systems vary considerably upon different acceptors, requiring renewed case-by-case reaction optimization. Herein, we developed an iron condition that enables highly efficient decarboxylation various carboxylic acids for a range transformations. This operationally simple protocol was amenable to wide array delivering structurally diverse oxime ethers, alkenylation, alkynylation, thiolation, and amidation products in useful excellent yields (>40 examples, up 95% yield).

Language: Английский

Citations

16

Visible-light induced direct C(sp3)–H functionalization: recent advances and future prospects DOI
Jia‐Lin Tu, Yining Zhu, Pengcheng Li

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(18), P. 5278 - 5305

Published: Jan. 1, 2024

This review summarizes the latest methodological advances in photocatalytic C(sp 3 )–H functionalization, with a particular emphasis on formation of C–P, C–B, C–S bonds, etc ., and some prominent efforts asymmetric C–H functionalization.

Language: Английский

Citations

16

Unleashing the potentiality of metals: synergistic catalysis with light and electricity DOI
Zhengjia Shen, Jia‐Lin Tu, Binbin Huang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(14), P. 4024 - 4040

Published: Jan. 1, 2024

This review provides a comprehensive overview of metal catalysis in photo-electrochemical systems, discussing reaction mechanisms and offering prospects for this triadic catalytic mode.

Language: Английский

Citations

13

Direct C(sp3)-H functionalization with aryl and alkyl radicals as intermolecular hydrogen atom transfer (HAT) agents DOI
Jia‐Lin Tu, Binbin Huang

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Recent years have witnessed the emergence of direct intermolecular C(sp

Language: Английский

Citations

7

Photoinduced C−O Bond Formation through C−C Bond Cleavage of Alcohols by Suppressing Alcohol Oxidation DOI
Qiang Wu, Peng Hu

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(7), P. 1595 - 1605

Published: Feb. 3, 2024

Abstract Herein, we present a photoinduced deconstructive alkoxyamination of alkyl alcohols catalyzed by iron salts. This transformation involves the initiation alkoxy radicals through chlorine radical‐induced radical formation, followed β ‐scission and trapping resulting carbon with 2,2,6,6‐tetramethylpiperidin‐1‐yl (TEMPO). reaction exhibits broad substrate scope (40 examples), including primary secondary that are prone to oxidation combination TEMPO iron. Mechanistic investigations have revealed enhanced coordination chloride ion center inhibits OH process, thereby enabling tolerance alcohols.

Language: Английский

Citations

6

Photoinduced decatungstate-catalyzed C(sp3)–H thioetherification by sulfinate salts DOI
Pengcheng Li, Jia‐Lin Tu,

Ao-Men Hu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(17), P. 3420 - 3424

Published: Jan. 1, 2024

A visible light photoinduced decatungstate-catalyzed C(sp 3 )–H thioetherification of hydrocarbons by sodium sulfite is herein reported.

Language: Английский

Citations

5

Photoinduced difunctionalizations of unactivated olefins enabled by ligand-to-iron charge transfer and functional group migration strategies DOI

Mengqi Luo,

Shibo Zhu,

Jiawen Yin

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(17), P. 4748 - 4756

Published: Jan. 1, 2024

Difunctionalizations of unactivated olefins with fluoroalkyl carboxylic acids or aldehydes via a radical-mediated functional group migration strategy are herein reported.

Language: Английский

Citations

5

Photocatalytic decarboxylation of free carboxylic acids and their functionalization DOI

Subal Mondal,

Subham Mandal,

Soumya Mondal

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(72), P. 9645 - 9658

Published: Jan. 1, 2024

This highlight article summarizes the complete development of photodecarboxylative functionalization free carboxylic acids via a concerted single electron transfer (SET) or energy (ET) pathways.

Language: Английский

Citations

5