Catalytic Enantioselective C–C Coupling of Alcohols for Polyketide Total Synthesis beyond Chiral Auxiliaries and Premetalated Reagents DOI
Jessica Wu,

Katherine L. Verboom,

Michael J. Krische

et al.

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

Published: Dec. 6, 2024

Catalytic enantioselective hydrogen autotransfer reactions for the direct conversion of lower alcohols to higher are catalogued and their application total synthesis polyketide natural products is described. These methods exploit a redox process in which alcohol oxidation balanced by reductive generation organometallic nucleophiles from unsaturated hydrocarbon pronucleophiles. Unlike classical carbonyl additions, premetalated reagents, chiral auxiliaries discrete alcohol-to-aldehyde not required. Additionally, chemoselective dehydrogenation primary presence secondary enables C-C coupling absence protecting groups.

Language: Английский

3d Transition Metals for C–H Activation DOI
Parthasarathy Gandeepan, Thomas Müller, Daniel Zell

et al.

Chemical Reviews, Journal Year: 2018, Volume and Issue: 119(4), P. 2192 - 2452

Published: Nov. 27, 2018

C–H activation has surfaced as an increasingly powerful tool for molecular sciences, with notable applications to material crop protection, drug discovery, and pharmaceutical industries, among others. Despite major advances, the vast majority of these functionalizations required precious 4d or 5d transition metal catalysts. Given cost-effective sustainable nature earth-abundant first row metals, development less toxic, inexpensive 3d catalysts gained considerable recent momentum a significantly more environmentally-benign economically-attractive alternative. Herein, we provide comprehensive overview on until summer 2018.

Language: Английский

Citations

1970

Iridium-Catalyzed Asymmetric Allylic Substitution Reactions DOI
Qiang Cheng, Hang‐Fei Tu, Chao Zheng

et al.

Chemical Reviews, Journal Year: 2018, Volume and Issue: 119(3), P. 1855 - 1969

Published: Dec. 24, 2018

In this review, we summarize the origin and advancements of iridium-catalyzed asymmetric allylic substitution reactions during past two decades. Since first report in 1997, Ir-catalyzed have attracted intense attention due to their exceptionally high regio- enantioselectivities. been significantly developed recent years many respects, including ligand development, mechanistic understanding, substrate scope, application synthesis complex functional molecules. an explicit outline ligands, mechanism, scope nucleophiles, applications is presented.

Language: Английский

Citations

674

Organic synthesis with the most abundant transition metal–iron: from rust to multitasking catalysts DOI
Sujoy Rana, Jyoti Prasad Biswas,

Sabarni Paul

et al.

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(1), P. 243 - 472

Published: Jan. 1, 2021

The promising aspects of iron in synthetic chemistry are being explored for three-four decades as a green and eco-friendly alternative to late transition metals. This present review unveils these rich iron-chemistry towards different transformations.

Language: Английский

Citations

263

Metalated covalent organic frameworks: from synthetic strategies to diverse applications DOI
Qun Guan, Lele Zhou, Yu‐Bin Dong

et al.

Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(15), P. 6307 - 6416

Published: Jan. 1, 2022

This review highlights the recent advances of metalated covalent organic frameworks, including synthetic strategies and applications, discusses current challenges future directions.

Language: Английский

Citations

215

Transition Metal‐Catalyzed Intermolecular Cascade C−H Activation/Annulation Processes for the Synthesis of Polycycles DOI
Liangliang Song, Erik V. Van der Eycken

Chemistry - A European Journal, Journal Year: 2020, Volume and Issue: 27(1), P. 121 - 144

Published: June 12, 2020

Abstract Polycycles are abundantly present in numerous advanced chemicals, functional materials, bioactive molecules and natural products. However, the strategies for synthesis of polycycles limited to classical reactions transition metal‐catalyzed cross‐coupling reactions, requiring pre‐functionalized starting materials lengthy synthetic operations. The emergence novel approaches shows great promise fields organic/medicinal/materials chemistry. Among them, C−H activation followed by intermolecular annulation prevail, due their straightforward manner with high atom‐ step‐economy, providing rapid, concise efficient methods construction diverse polycycles. Several have been developed polycycles, relying on sequential multiple activation/annulation, or combination activation/annulation further interaction a proximal group, merger cycloaddition reaction, situ formation directing group. These attractive, efficient, step‐ atom‐economic from commercially available materials. This Minireview will provide an introduction helping researchers discover indirect connections reveal hidden opportunities. It also promote discovery activation.

Language: Английский

Citations

85

C–H Functionalization of Aromatic Amides DOI

Quan Zheng,

Chenfu Liu, Jie Chen

et al.

Advanced Synthesis & Catalysis, Journal Year: 2019, Volume and Issue: 362(7), P. 1406 - 1446

Published: Dec. 9, 2019

Abstract Since the beginning of 21 st century, significant progress has been made in transition metal‐catalyzed C–H functionalization aromatic amides. The achievements this field have mainly focused on ortho (proximal) functionalization, there far fewer reports remote and para‐ meta‐ selective functionalizations remain a major challenge. Interestingly, are few related comments field. In published cases, scope report is relatively narrow, either to comment specific directing group or summarize reaction site. Herein, for first time, we comprehensively summarized This review divided into three parts: ortho‐ , amides, subdivided according type catalyst. groups, types, conditions, mechanism applications corresponding reactions discussed detail. magnified image

Language: Английский

Citations

76

Photoinduced C–H arylation of 1,3-azoles via copper/photoredox dual catalysis DOI Creative Commons
Sven Trienes, Jiawei Xu, Lutz Ackermann

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(19), P. 7293 - 7299

Published: Jan. 1, 2024

The photo-induced azole C–H arylation was realized with a dual-catalytic copper-based system. Exceedingly mild reaction conditions at ambient temperature and visible light irradiation enabled broad scope high functional group tolerance.

Language: Английский

Citations

14

Recent Development on Cp*Ir(III)‐Catalyzed C−H Bond Functionalization DOI
Xianwei Li, Wensen Ouyang,

Jianhong Nie

et al.

ChemCatChem, Journal Year: 2019, Volume and Issue: 12(9), P. 2358 - 2384

Published: Dec. 18, 2019

Abstract Selective functionalization of ubiquitous C−H bonds molecules would provide novel retrosynthetic insights and powerful tools for the rapid construction molecular complexity. In this context, Cp*Ir(III) complexes have exhibited versatile reactivity towards selective conversion bonds, with key features that include use readily transformable raw materials, great selectivity (chemo‐, stereo‐ regio‐), high efficiency, mild reaction conditions they enable late‐stage modification complex molecules. Recently, catalysis has achieved a broad range reactions such as multiple dehydrogenations stereoselective C−X bond formations. These advancements are valuable to organometallic chemists efficient synthesis functionalized architectures.

Language: Английский

Citations

58

Hydroxyl Group‐Prompted and Iridium(III)‐Catalyzed Regioselective C−H Annulation of N‐phenoxyacetamides with Propargyl Alcohols DOI
Weijie Chen,

Fu‐Xiaomin Liu,

Wanchun Gong

et al.

Advanced Synthesis & Catalysis, Journal Year: 2018, Volume and Issue: 360(13), P. 2470 - 2475

Published: April 27, 2018

Abstract An efficient, mild and redox‐neutral iridium(III)‐catalyzed C−H annulation of N ‐phenoxyacetamides for the regioselective synthesis benzofurans has been developed by employing tertiary propargyl alcohols as versatile coupling partners. The computed results together with experimental data revealed that hydroxyl group acts key factor in controlling regioselectivity tuning reactivity. magnified image

Language: Английский

Citations

50

Applications of Transition‐Metal‐Catalyzed Asymmetric Allylic Substitution in Total Synthesis of Natural Products: An Update DOI
Leyla Mohammadkhani, Majid Μ. Heravi

The Chemical Record, Journal Year: 2020, Volume and Issue: 21(1), P. 29 - 68

Published: Nov. 18, 2020

Abstract Metal‐catalyzed asymmetric allylic substitution (AAS) reaction is one of the most synthetically useful reactions catalyzed by metal complexes for formation carbon‐carbon and carbon‐heteroatom bonds. It comprises substrates with a wide range nucleophiles or S N 2′‐type substitution, which results in above‐mentioned bonds high levels enantioselective induction. AAS tolerates broad functional groups, thus has been successfully applied synthesis optically pure compounds. This extensively used total several complex molecules, especially natural products. In this review, we try to highlight applications (Pd, Ir, Mo, Cu)‐catalyzed biologically active products, as key step, updating subject from 2003 till date.

Language: Английский

Citations

43