Reductive electrophilic C–H alkylation of quinolines by a reusable iridium nanocatalyst DOI Creative Commons

Rong Xie,

Wenhui Mao,

Huanhuan Jia

et al.

Chemical Science, Journal Year: 2021, Volume and Issue: 12(41), P. 13802 - 13808

Published: Jan. 1, 2021

The incorporation of a coupling step into the reduction unsaturated systems offers desirable way for diverse synthesis functional molecules, but it remains to date challenge due difficulty in controlling chemoselectivity. Herein, by developing new heterogeneous iridium catalyst composed Ir-species (Ir δ+) and N-doped SiO2/TiO2 support (Ir/N-SiO2/TiO2), we describe its application reductive electrophilic mono dialkylations quinolines with various 2- or 4-functionalized aryl carbonyls benzyl alcohols utilizing renewable formic acid as reductant. This catalytic transformation practical platform direct access vast range alkyl THQs, proceeding excellent atom-efficiency, good substrate scope group tolerance, reusable abundantly available feedstocks, generation water carbon dioxide by-products. work opens door further develop more useful organic transformations under catalysis.

Language: Английский

Progress in the Chemistry of Tetrahydroquinolines DOI

Isravel Muthukrishnan,

Vellaisamy Sridharan, J. Carlos Menéndez

et al.

Chemical Reviews, Journal Year: 2019, Volume and Issue: 119(8), P. 5057 - 5191

Published: April 9, 2019

Tetrahydroquinoline is one of the most important simple nitrogen heterocycles, being widespread in nature and present a broad variety pharmacologically active compounds. This Review summarizes progress achieved chemistry tetrahydroquinolines, with emphasis on their synthesis, during period from mid-2010 to early 2018.

Language: Английский

Citations

390
Reductive Functionalization of Pyridine-Fused N-Heteroarenes DOI
Huanhuan Jia, Zhenda Tan, Min Zhang

et al.

Accounts of Chemical Research, Journal Year: 2024, Volume and Issue: 57(5), P. 795 - 813

Published: Feb. 23, 2024

ConspectusThe selective functionalization/transformation of ubiquitous pyridine-fused N-heteroarenes is a practical method to synthesize structurally novel N-heterocycles, which important for the development medicines, bioactive agents, agrochemicals, materials, ligands, sensors, pigments, dyes, etc. However, owing thermodynamic stability, kinetic inertness, and lone electron pair–induced catalyst deactivation N-heteroarenes, limited strategies (e.g., C–H activation/functionalization, electrophilic substitution, Minisci reaction) are available realize synthetic purpose maintain aromaticity final products. Moreover, relevant transformations have limitations such as needing harsh reaction conditions, requiring preinstallation specific coupling agents containing transformable functionalities or directing groups, using less environmentally benign oxidants and/or acidic activators, poor selectivity. Herein, considering that imines, enamines, radicals, cyclic amines generated during reduction precise transformation these reductive intermediates offers fundamental basis developing tandem reactions. Our group revealed slow rate, synergistic catalysis, controlled electroreduction effective fulfilling functionalization N-heteroarenes. Thus, we established series new methods provide diverse construction modalities functionalized N-heterocycles. The striking features include high efficiency, atom economy, use readily accessible feedstocks in absence flammable pressurized H2 gas, alongside promising potential obtained N-heterocyclic present study would be appealing fields organic chemistry, biomedical functional materials. This Account describes application dearomatization substrate-activating reaction-initiating modes summarizes via alkylation, arylation, annulation at nitrogen, α, β, other remote carbon sites achieved over past 8 years. Details regarding reactions their plausible mechanisms perspectives discussed. We hope our contributions this field will aid further tackle intractable challenges area.

Language: Английский

Citations

16
BINAP-copper supported by hydrotalcite as an efficient catalyst for the borrowing hydrogen reaction and dehydrogenation cyclization under water or solvent-free conditions DOI

Zhaojun Xu,

Xiaoli Yu,

Xinxin Sang

et al.

Green Chemistry, Journal Year: 2018, Volume and Issue: 20(11), P. 2571 - 2577

Published: Jan. 1, 2018

A BINAP-Cu system supported by hydrotalcite has been developed and proved to be a highly efficient catalyst for the atom-efficient green borrowing hydrogen reaction dehydrogenative cyclization.

Language: Английский

Citations

113
MOF-Derived Nanocobalt for Oxidative Functionalization of Cyclic Amines to Quinazolinones with 2-Aminoarylmethanols DOI
Feng Xie, Qinghua Chen,

Rong Xie

et al.

ACS Catalysis, Journal Year: 2018, Volume and Issue: 8(7), P. 5869 - 5874

Published: May 25, 2018

By employing a MOF-templated method, we have developed highly dipersed and ultralow loading cobalt nanocatalyst, which has been applied in the oxidative functionalization of easily available cyclic amines with 2-aminoarylmethanols to ring-fused quinazolinones, core structures numerous valuable products. The catalytic transformation proceeds merits broad substrate scope, good functional group tolerance chemoselectivity, high step- atom-efficiency, use naturally abundant Co/O2 system, offers practical way for preparation quinazolinones structural diversity. work presented built an important basis direct conversion amine motifs into frameworks.

Language: Английский

Citations

83
Unsymmetrical indazolyl-pyridinyl-triazole ligand-promoted highly active iridium complexes supported on hydrotalcite and its catalytic application in water DOI

Chenyang Ge,

Xinxin Sang,

Wei Yao

et al.

Green Chemistry, Journal Year: 2018, Volume and Issue: 20(8), P. 1805 - 1812

Published: Jan. 1, 2018

Herein, an indazolyl-pyridinyl-triazole ligand was synthesized and its iridium complex supported on hydrotalcite developed.

Language: Английский

Citations

76
Merrifield resin-supported quinone as an efficient biomimetic catalyst for metal-free, base-free, chemoselective synthesis of 2,4,6-trisubstituted pyridines DOI
Qing Yang, Yilin Zhang, Wei Zeng

et al.

Green Chemistry, Journal Year: 2019, Volume and Issue: 21(20), P. 5683 - 5690

Published: Jan. 1, 2019

Metal-free, base-free, biomimetic, and chemoselective synthesis of 2,4,6-trisubstituted pyridines was developed for the first time under mild conditions.

Language: Английский

Citations

66
Preparation of pyridyltriazole ruthenium complexes as effective catalysts for the selective alkylation and one-pot C–H hydroxylation of 2-oxindole with alcohols and mechanism exploration DOI
Qiang Wu, Le Pan,

Guangming Du

et al.

Organic Chemistry Frontiers, Journal Year: 2018, Volume and Issue: 5(18), P. 2668 - 2675

Published: Jan. 1, 2018

Pyridyltriazole-ligated ruthenium(ii) complexes have been designed and synthesized, which were characterized by X-ray crystallography.

Language: Английский

Citations

64
Unsymmetrical triazolyl-naphthyridinyl-pyridine bridged highly active copper complexes supported on reduced graphene oxide and their application in water DOI
Wenkang Hu, Yilin Zhang, Haiyan Zhu

et al.

Green Chemistry, Journal Year: 2019, Volume and Issue: 21(19), P. 5345 - 5351

Published: Jan. 1, 2019

A clean method for the synthesis of functionalized quinolines in water with a recoverable copper catalyst was developed.

Language: Английский

Citations

64
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
Synthesis of difluoromethylated allenes through trifunctionalization of 1,3-enynes DOI Creative Commons
Munira Taj Muhammad,

Yihang Jiao,

Changqing Ye

et al.

Nature Communications, Journal Year: 2020, Volume and Issue: 11(1)

Published: Jan. 21, 2020

Abstract Organofluorine compounds have shown their great value in many aspects. Moreover, allenes are also a class of important compounds. Fluorinated or fluoroalkylated might provide an option as candidates for drug and material developments, allow number valuable transformations. Herein, we report metal-free synthesis difluoromethylated via regioselective trifunctionalization 1,3-enynes. This method proceeds through double C–F bond formation with concomitant introduction amino group to the allene. Synthetic applications conducted preliminary mechanistic studies suggest that two-step pathway is involved. DFT calculations revealed unusual dibenzenesulfonimide-assisted fluorination/fluoroamination NFSI. In addition, kinetic reaction study induction period both major side products support proposed mechanism. work offers convenient approach range rare example

Language: Английский

Citations

58