Reductive deaminative cross-coupling of alkyl bistriflimides enabled by electrocatalysis DOI Creative Commons
Xiangzhang Tao, Wooseok Lee,

Zhimin Xu

et al.

Science Advances, Journal Year: 2024, Volume and Issue: 10(47)

Published: Nov. 22, 2024

We present a versatile nickel-electrocatalytic deaminative cross-coupling platform for the efficient construction of C(sp 3 )–C(sp ) and 2 bonds from readily available alkyl bistriflimides. This methodology involves assembly two leaving groups on amines to form bistriflimides, followed by their effective coupling with wide range halides, pseudohalides, aryl alkenyl halides under electrochemical reductive conditions. Moreover, successful application relay transition metal–free cross-electrophile further demonstrates versatility bistriflimides as valuable building blocks in organic synthesis. Combined control experiments density functional theory calculations provide insights into reaction pathway crucial role iodide catalytic process.

Language: Английский

A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis DOI Creative Commons
Nian Li, Ruzal Sitdikov, Ajit Prabhakar Kale

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 2500 - 2566

Published: Oct. 9, 2024

With the resurgence of electrosynthesis in organic chemistry, there is a significant increase number routes available for late-stage functionalization (LSF) drugs. Electrosynthetic methods, which obviate need hazardous chemical oxidants or reductants, offer unprecedented control reactions through continuous variation applied potential and possibility combination with photochemical processes. This capability substantial advantage performing electrochemical photoelectrochemical LSF. Ultimately, these protocols are poised to become vital component medicinal chemist's toolkit. In this review, we discuss that have been demonstrated be applicable LSF pharmaceutical drugs, their derivatives, natural substrates. We present analyze representative examples illustrate electrochemistry photoelectrochemistry valuable molecular scaffolds.

Language: Английский

Citations

6
Electrosynthesis of 1,4-diene derivatives bearing cyclopentene skeleton DOI Creative Commons

Yaqi Qiao,

Xiaoqing Fan,

Chengcheng Yuan

et al.

iScience, Journal Year: 2025, Volume and Issue: 28(3), P. 111976 - 111976

Published: Feb. 10, 2025

1,n-Dual Π systems including 1,4-diene derivatives have been widely used as the elegant radical receptors to promote cascade additions give highly functionalized polycyclic scaffolds. However, tedious and complicated preparation of former deters broad utilization compromises practical value. Herein, a straightforward was developed from easily accessible alkynes γ,δ-unsaturated carboxylic acids via electrochemical oxidation cyclization Hofmann elimination. This transformation features with good excellent yields, functional group compatibility, selectivity without any Zaitsev elimination product detected.

Language: Английский

Citations

0
N-Alkoxyphthalimides as Nitrogen Electrophiles to Construct C–N Bonds via Reductive Cross-Coupling DOI
Kang Wu,

Tian‐Zhang Wang,

Chao‐Peng Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10004 - 10011

Published: June 27, 2024

-Alkoxyphthalimides, one kind of phthalimide derivative, have great importance in synthesis, mainly used as free radical precursors. While the unit, for a long time, was treated part waste stream. Construction C-N bonds has always been hot spot, especially reductive cross-coupling. Herein, nickel-catalyzed cross-coupling reaction

Language: Английский

Citations

2
Precision Propargylic Substitution Reaction: Pd-Catalyzed Suzuki–Miyaura Coupling of Nonactivated Propargylamines with Boronic Acids DOI
Yan Sun, Tao Zhao, Haixiang Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 31, 2024

Palladium-catalyzed Suzuki–Miyaura cross-coupling is an efficient approach for C–C bond construction. Here we report a deaminative reaction to achieve chemo- and regioselectivity in the of nonactivated propargylamines with boronic acids, which methyl propiolate introduced promote cleavage C–N form bond. This method features wide range substrates, good functional group tolerance, ease operation, providing alternative accessing valuable propargylated aromatic compounds.

Language: Английский

Citations

2
Electrochemical Nickel-Catalyzed Synthesis of Unsymmetrical Diorganyl Selanes from Diaryl Diselanes and Aryl and Alkyl Iodides DOI Creative Commons

Jona Queder,

Gerhard Hilt

Molecules, Journal Year: 2024, Volume and Issue: 29(19), P. 4669 - 4669

Published: Oct. 1, 2024

The synthesis of unsymmetrical diorganyl selanes was accomplished under electrochemical conditions in an undivided cell utilizing a magnesium cathode and carbon anode made out aryl alkyl iodides diselanes. This cross-electrophile coupling (eXEC) using simple nickel catalyst formed situ Ni(acac)2 2,2′-bipyridine DMF at ambient temperatures. reaction showed good functional group compatibility, heteroaryl iodides, such as thiophene or pyridine derivatives, were well accepted.

Language: Английский

Citations

2
Electrochemical Decarboxylative Cross‐Coupling with Nucleophiles DOI

Pingping Yu,

Xuejin Huang, Dake Wang

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 19, 2024

Decarboxylative cross-coupling reactions are powerful tools for carbon-heteroatom bonds formation, but typically require pre-activated carboxylic acids as substrates or heteroelectrophiles functional groups. Herein, we present an electrochemical decarboxylative of with structurally diverse fluorine, alcohol, H

Language: Английский

Citations

1
Electroreduction Reactions Mediated by Organic Molecules: Recent Advances and Applications DOI Open Access
Yubing Huang

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(47)

Published: Aug. 27, 2024

Abstract Electroreduction is an important aspect of organic electrochemistry. Its chemistry does not require the addition additional reductants, making it effective alternative to various traditional reduction reactions. Among them, organo‐mediated electroreduction recognized as a promising approach. Organo‐mediators can be reduced directly at cathode form reactive radical anions that subsequently reduce substrate via electron transfer ( ET ) initiate reaction being investigated. typically have more positive potential, and their role in whole similar catalysts. Their transforms process from original heterogeneous into homogeneous one. Organo‐mediated effectively avoid over‐electrolysis product electrode intolerance sensitive substrates or functional groups during electrolysis, thereby preventing occurrence side It also prevent excessive consumption reagents electrical energy while promoting achieve higher completely different selectivity. Considering advantages this type reaction, review will provide detailed description reactions mediated by molecules recent years elucidate mechanism organo‐mediators transformations.

Language: Английский

Citations

1
Direct Decarboxylative C−N Coupling with Dioxazolones Mediated by a Base DOI

Bai-Hua Niu,

Xi‐Rui Xia,

Ran Lu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

By reacting carboxylic acids with dioxazolones in the presence of a base, wide variety amides, particularly acylated chiral amines, can be synthesized through decarboxylative amidation.

Language: Английский

Citations

1
Divergent Reactivity of Iminyl Radicals in Four Interrupted Pathways for the Synthesis of Cyclic/Acyclic Ketones and N-Heterocycles from Vinyl Azides and Phenylacetic Acids DOI

Swagota Paul,

A. K. BARUAH,

Atul A. More

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13128 - 13136

Published: Sept. 11, 2024

Herein, we report the Ag-catalyzed substrate-controlled interrupted radical pathways of iminyl radical. The benzylic groups played a crucial role in pathway selection involving series dimerization and hydrolysis, 1,5-H shift followed by cascade cyclization, direct N-(sp

Language: Английский

Citations

1
Graphical Abstract: Angew. Chem. Int. Ed. 12/2024 DOI Open Access

Anna Hartmann,

Tobias E. Schrader, Stefan Kubik

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(12)

Published: March 11, 2024

Lithium-Ion BatteriesIn their Communication (e202315628), De-en Jiang et al. reveal through machine-learning force field molecular dynamics simulations the superionic Li + transport in glassy LiTaCl 6 via adynamic "monkey bar" mechanism.

Language: Английский

Citations

0