Recent progress in remote γ-C(sp<sup>3</sup>)–H functionalization of carboxylic acid derivatives DOI
Yueting Huang, Dong Zou

Scientia Sinica Chimica, Journal Year: 2023, Volume and Issue: 53(6), P. 932 - 957

Published: Feb. 13, 2023

碳氢键选择性活化是化学领域中最基本和最具挑战性的问题之一，在合成各种生物活性物质中具有重要的作用. 羧酸及其衍生物是最易获得的原料之一. 通常羧酸的α-和β-C(sp3)–H键官能化较为容易，而γ-和δ-C(sp3)–H因距离较远则难以官能化. 因此，发展简便、高效的方法实现羧酸及其衍生物远程C(sp3)–H键官能团化成为近年研究热点之一. 本文根据不同反应分类, 综述了近些年在不同催化条件下基于羧酸衍生物的远程γ-C(sp3)–H键官能团化反应研究进展, 详细讨论了反应底物普适性、反应机理和应用, 并对该领域的发展前景和局限性进行了总结.

Language: Английский

A survey of the iron ligand-to-metal charge transfer chemistry in water DOI
J Stahl,

Burkhard König

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(6), P. 3058 - 3071

Published: Jan. 1, 2024

Fully hydrated! – Iron photocatalysis tests the waters.

Language: Английский

Citations

11
Ru‐, Rh‐ and Ir‐Catalyzed Enantioselective sp3C−H Functionalization DOI
Ramandeep Kaur, Nidhi Jain

Chemistry - An Asian Journal, Journal Year: 2022, Volume and Issue: 17(24)

Published: Oct. 22, 2022

Abstract The development of novel methodologies that enable the construction complex chiral molecular scaffolds in an atom and step‐economic manner has always been area immense interest significant synthetic value. transition metal‐catalyzed enantioselective sp 3 C−H activation functionalization reactions serve as expeditious means for introducing diverse functionalities a straightforward manner. However, controlling chemo‐ stereoselectivity these is challenge owing to their ubiquity low reactivity. In this review, we present comprehensive account on recent advances inter‐ intramolecular asymmetric bond utilizing ruthenium, rhodium, iridium catalysts get insights into mechanistic aspects transformations.

Language: Английский

Citations

10
Ru(II)-Catalyzed Weakly Coordinating Carbonyl-Assisted Dialkynylation of (Hetero)Aryl Ketones DOI

Akanksha Singh Baghel,

Ramendra Pratap, Amit Kumar

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(13), P. 8542 - 8552

Published: June 12, 2023

Functionalized aryl(heteroaryl) ketones are present in many natural products as key structural components and serve basic synthetic building blocks for various organic transformation reactions. Therefore, the development of an effective sustainable route making these classes compounds remains challenging yet highly desirable. Herein, we report a simple efficient catalytic system dialkynylation aromatic/heteroaromatic via double C–H bond activation presence less expensive ruthenium(II)-salt catalyst using weakly native carbonyl group desired directing group. The developed protocol is compatible, tolerant, toward functional groups. utility has been demonstrated through scale-up synthesis transformation. Control experiments support involvement base-assisted internal electrophilic substitution (BIES) reaction pathway.

Language: Английский

Citations

4
Recent Advances in the Transformation Reactions of Aromatic Nitriles via C—CN Bond Cleavage DOI Open Access

Cunjing Miao,

Jiaqi Yao

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(4), P. 1341 - 1341

Published: Jan. 1, 2023

Aromatic nitriles are one of the ubiquitous versatile materials in organic synthesis, and also a class important synthetic intermediates for wide range applications pharmaceuticals, agricultural chemicals, dyes, spices, functional materials.However, C-CN bond aryl has rarely been considered as valuable reaction site due to high thermodynamic stability.Therefore, development simple efficient methods catalyze transformation become hot research topics recent years.In this review, advances reactions aromatic via cleavage past decade summarized classified according different mechanisms, mainly including transition metal-mediated/catalyzed transformation, free radical-mediated Lewis acid, base or Brønsted acid-mediated transformation.The substrate compatibility, mechanism, applications, advantages limitations field discussed detail.

Language: Английский

Citations

2
Carboxylate-Directed Pd-Catalyzed β-C(sp3)–H Arylation of N-Methyl Alanine Derivatives for Diversification of Bioactive Peptides DOI
Suyeon Yeom, Do Young Kim, Seungwoo Kim

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(50), P. 9008 - 9013

Published: Dec. 12, 2023

This study presents a Pd(II)-catalyzed method for the β-C(sp3)–H arylation of N-Cbz- or N-Fmoc-protected N-methyl alanines, providing ready access to building blocks N-methylated peptide synthesis. For this transformation, native carboxylate was exploited as directing group, attributing its success use monoprotected amino-pyridine ligand. Its synthetic utility demonstrated by facile generation nine analogues naturally occurring cyclic cycloaspeptide A.

Language: Английский

Citations

2
Recent progress in remote γ-C(sp<sup>3</sup>)–H functionalization of carboxylic acid derivatives DOI
Yueting Huang, Dong Zou

Scientia Sinica Chimica, Journal Year: 2023, Volume and Issue: 53(6), P. 932 - 957

Published: Feb. 13, 2023

碳氢键选择性活化是化学领域中最基本和最具挑战性的问题之一，在合成各种生物活性物质中具有重要的作用. 羧酸及其衍生物是最易获得的原料之一. 通常羧酸的α-和β-C(sp3)–H键官能化较为容易，而γ-和δ-C(sp3)–H因距离较远则难以官能化. 因此，发展简便、高效的方法实现羧酸及其衍生物远程C(sp3)–H键官能团化成为近年研究热点之一. 本文根据不同反应分类, 综述了近些年在不同催化条件下基于羧酸衍生物的远程γ-C(sp3)–H键官能团化反应研究进展, 详细讨论了反应底物普适性、反应机理和应用, 并对该领域的发展前景和局限性进行了总结.

Language: Английский

Citations

1