Pd-Catalyzed Decarbonylative sp2 C–H Arylation: Construction of Five- and Six-Membered (Hetero)Cyclic Compounds DOI
Shan‐Shan Zhang,

Mengjie Cen,

Chenglong Li

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(22), P. 4660 - 4665

Published: May 24, 2024

The cyclic compounds have wide applications in the design and synthesis of drugs materials; thus, their efficient construction attracts much attention from synthetic community. In this letter, we report an method for preparing starting readily available carboxylic acids. This reaction takes place through intramolecular decarbonylative sp2 C–H arylation, enabling a range five- six-membered compounds. Both carbo- heterocycles can be produced under conditions. Moreover, features substrate scope with high functional group tolerance. scale-up experiments also show its practicality organic synthesis. Those experimental results indicate that would find

Language: Английский

Aliphatic sulfonyl fluoride synthesis via reductive decarboxylative fluorosulfonylation of aliphatic carboxylic acid NHPI esters DOI

Zhanhu Ma,

Yongan Liu, Xiaoyu Ma

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(4), P. 1115 - 1120

Published: Jan. 1, 2022

A general and efficient approach to various aliphatic sulfonyl fluorides by the reductive decarboxylative fluorosulfonylation of carboxylic acids via a radical sulfur dioxide insertion fluorination strategy was developed.

Language: Английский

Citations

39
Recent advances on electrochemical generation of sulfonyl radical triggered cyclization of alkene/alkynes DOI

Jiaqing Shao,

Jiang Liu, Haibo Mei

et al.

Tetrahedron, Journal Year: 2025, Volume and Issue: 173, P. 134467 - 134467

Published: Jan. 12, 2025

Language: Английский

Citations

1
Electrophotochemical Metal‐Catalyzed Decarboxylative Coupling of Aliphatic Carboxylic Acids DOI
Kai Yang, Jiaqing Lu, Liubo Li

et al.

Chemistry - A European Journal, Journal Year: 2022, Volume and Issue: 28(70)

Published: Sept. 21, 2022

An electrophotochemical dual metal-catalyzed protocol for decarboxylative arylation of simple aliphatic carboxylic acids with aryl halides is reported. The relative stabilities catalytically active metal complexes simultaneously generated at anode and cathode are the key design elements success this convergent paired electrolysis. This new electrophotocatalytic method mild, robust, most importantly, capable accommodating primary including acetic acid - ubiquitous variegated structural motifs yet remain oddly challenging substrates directly as native functional groups C(sp2 )-C(sp3 ) bond formation.

Language: Английский

Citations

35
Nickel-catalyzed decarboxylative cross-coupling of indole-3-acetic acids with aryl bromides by convergent paired electrolysis DOI
Zhenhua Wang, Lei Wei,

Ke‐Jin Jiao

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(59), P. 8202 - 8205

Published: Jan. 1, 2022

Herein, nickel-catalyzed decarboxylative cross-coupling of indole-3-acetic acids with aryl bromides by convergent paired electrolysis was developed in an undivided cell. This protocol features good functional group tolerance, and is chemical redox agent- sacrificial electrode-free. Mechanistic studies indicated that the base crucial for decarboxylation step a NiI/NiIII catalytic cycle involved this transformation.

Language: Английский

Citations

34
Electrochemical Benzylic C(sp3)–H Acyloxylation DOI Creative Commons
Alexander Atkins, Albert C. Rowett, David M. Heard

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(28), P. 5105 - 5108

Published: July 13, 2022

The development of sustainable C(sp3)–H functionalization methods is great interest to the pharmaceutical and agrochemical industries. Anodic oxidation an efficient means producing benzylic cations that can undergo subsequent in situ nucleophilic attack afford functionalized products. Herein, we demonstrate suitability carboxylic acids as nucleophiles yield esters. This method employs a series secondary substrates demonstrated on gram scale flow.

Language: Английский

Citations

34
Catalyst-controlled functionalization of carboxylic acids by electrooxidation of self-assembled carboxyl monolayers DOI Creative Commons
Heather A. Hintz, Christo S. Sevov

Nature Communications, Journal Year: 2022, Volume and Issue: 13(1)

Published: March 14, 2022

While the electrooxidative activation of carboxylic acids is an attractive synthetic methodology, resulting transformations are generally limited to either homocoupling or further oxidation followed by solvent capture. These reactions require extensive electrolysis at high potentials, which ultimately renders methodology incompatible with metal catalysts that could possibly provide new and complementary product distributions. This work establishes a proof-of-concept for rare synthetically-underutilized strategy selective electrooxidation in presence oxidatively-sensitive control reaction selectivity. We leverage formation self-adsorbed monolayers carboxylate substrates anode promote adsorbed over more easily-oxidized catalyst. Consequently, operate lower greater faradaic efficiencies, improved catalyst compatibility conventional approaches, enables be performed inexpensive Fe complexes catalyze radical additions olefins.

Language: Английский

Citations

32
Electrochemical‐Induced Hydroxysulfonylation of α‐CF3 Alkenes to Access Tertiary β‐Hydroxysulfones DOI
Xu Luo, Shengchun Wang, Aiwen Lei

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(5), P. 1016 - 1022

Published: Jan. 25, 2022

Abstract An electrochemical hydroxysulfonylation of α‐CF 3 alkenes was accomplished in this work. By using easily available sodium sulfinates as the sulfonylating agents, a series valuable α‐trifluoromethyl tertiary alcohols were synthesized under mild and environmentally friendly electrolysis conditions moderate to good yields. The preliminary mechanistic investigation indicates that difunctional reaction involves radical process via sulfonyl radical. Gram‐scale synthesis shows significant potential application protocol. magnified image

Language: Английский

Citations

30
Electrochemical-induced benzyl C–H amination towards the synthesis of isoindolinones via aroyloxy radical-mediated C–H activation DOI
Mingming Yu, Yuhan Gao, Lin Zhang

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(4), P. 1445 - 1450

Published: Jan. 1, 2022

A novel electrochemical strategy for the synthesis of valuable isoindolinones has been developed with use simple o -alkylbenzoic acid and alkyl nitrile as starting materials under metal-catalyst external oxidant-free conditions.

Language: Английский

Citations

30
A Unified Synthetic Strategy to Introduce Heteroatoms via Electrochemical Functionalization of Alkyl Organoboron Reagents DOI
Su Yong Go, Hyunho Chung, Samuel Jaeho Shin

et al.

Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(20), P. 9149 - 9160

Published: May 16, 2022

Based on systematic electrochemical analysis, an integrated synthetic platform of C(sp3)-based organoboron compounds was established for the introduction heteroatoms. The electrochemically mediated bond-forming strategy shown to be highly effective functionalization sp3-hybridized carbon atoms with significant steric hindrance. Moreover, virtually all nonmetallic heteroatoms could utilized as reaction partners using one unified protocol. observed reactivity stems from two consecutive single-electron oxidations substrate, which eventually generates extremely reactive carbocation key intermediate. detailed profile elucidated through multifaceted studies. Ultimately, a new dimension in activation strategies accomplished driven development.

Language: Английский

Citations

25
Aliphatic Sulfonyl Fluoride Synthesis via Decarboxylative Fluorosulfonylation of Hypervalent Iodine(III) Carboxylates DOI

Caiyun Ou,

Yinxia Cai,

Yuyang Ma

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(36), P. 6751 - 6756

Published: Sept. 1, 2023

We disclose herein a photocatalytic decarboxylative fluorosulfonylation reaction of various hypervalent iodine(III) carboxylates in combination with 1,4-diazabicyclo[2.2.2]octane–bis(sulfur dioxide) adduct as sulfonyl source and KHF2 desirable fluorine via radical sulfur dioxide insertion fluorination strategy. A one-pot carboxylic acids mediated by PhI(OAc)2 was realized, well. Notably, this transformation can be performed under heating conditions without the need for catalysts.

Language: Английский

Citations

15