Ligand-Controlled Copper(I)-Catalyzed Cross-Coupling of Secondary and Primary Alcohols to α-Alkylated Ketones, Pyridines, and Quinolines

Organic Letters, Journal Year: 2018, Volume and Issue: 20(3), P. 608 - 611

Published: Jan. 16, 2018

One hexanuclear Cu(I) cluster of 4,6-dimethylpyrimidine-2-thiolate efficiently catalyzes the dehydrogenative cross-coupling secondary and primary alcohols to α-alkylated ketones with high selectivity. This transformation proceeds through a one-pot sequence dehydrogenation alcohols, condensation aldehydes ketones, hydrogenation resulting α,β-unsaturated generate ketones. catalytic system also displays activity for annulation reaction γ-amino- 2-aminobenzyl yield pyridines quinolines, respectively.

Language: Английский

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Direct Reductive Quinolyl β-C–H Alkylation by Multispherical Cavity Carbon-Supported Cobalt Oxide Nanocatalysts

ACS Catalysis, Journal Year: 2017, Volume and Issue: 7(7), P. 4780 - 4785

Published: June 12, 2017

Until now, the selective (hetero)aryl C–H alkylation without assistance of directing groups or preinstallation functionalities still remains a highly challenging goal. Herein, by developing acid-resistant multispherical cavity carbon-supported cobalt oxide nanocatalysts (CoOx/MSCC) and hydrogen transfer-mediated activation mode for nonactivated N-heteroaromatics, we present direct reductive quinolyl isoquinolyl β-C–H with various aldehydes as alkylating agents. The catalytic transformation features broad substrate scope, good functional tolerance, use Earth-abundant reusable catalysts, no need prefunctionalizations, demonstrating that developed enable one to directly functionalize inert N-heteroaryl systems are difficult realize organometallic complexes.

Language: Английский

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Hydrogen‐Transfer‐Mediated α‐Functionalization of 1,8‐Naphthyridines by a Strategy Overcoming the Over‐Hydrogenation Barrier

Angewandte Chemie International Edition, Journal Year: 2017, Volume and Issue: 56(45), P. 14232 - 14236

Published: Sept. 19, 2017

A general catalytic hydrogen transfer-mediated α-functionalization of 1,8-naphthyridines is reported for the first time that benefits from a activation mode non-activated pyridyl cores. The α-site selectively couples with C8-site various tetrahydroquinolines (THQs) to afford novel α-functionalized tetrahydro 1,8-naphthyridines, class synthetically useful building blocks and potential candidates discovery therapeutic bio-active products. utilization THQs as inactive donors (HDs) appears be key strategy overcome over-hydrogenation barrier address chemoselectivity issue. developed chemistry features operational simplicity, readily available catalyst good functional group tolerance, offers significant basis further development new protocols directly transform or functionalize inert N-heterocycles.

Language: Английский

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Tandem transformations and multicomponent reactions utilizing alcohols following dehydrogenation strategy

Organic & Biomolecular Chemistry, Journal Year: 2020, Volume and Issue: 18(12), P. 2193 - 2214

Published: Jan. 1, 2020

In this review, the progress of tandem transformation nitro, nitrile and azide functionalities is summarised to develop new C–C C–N bonds as well multi-component reactions using alcohols.

Language: Английский

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MOF-Derived Nanocobalt for Oxidative Functionalization of Cyclic Amines to Quinazolinones with 2-Aminoarylmethanols

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

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Transition-Metal Catalyzed Synthesis of Pyrimidines: Recent Advances, Mechanism, Scope and Future Perspectives

Topics in Current Chemistry, Journal Year: 2024, Volume and Issue: 382(1)

Published: Jan. 31, 2024

Language: Английский

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Aerobic Copper-Catalyzed Synthesis of Benzimidazoles from Diaryl- and Alkylamines via Tandem Triple C–H Aminations

ACS Catalysis, Journal Year: 2018, Volume and Issue: 8(3), P. 2242 - 2246

Published: Feb. 6, 2018

Through radical-induced tandem triple C–H aminations with free amines as the aminating agents, we herein present a precedent on aerobic copper-catalyzed synthesis of 5-diarylamino benzimidazoles, class optoelectronic device analogues by combining two molecules diarylamines and one molecule alkylamine in single operation. The developed chemistry proceeds merits natural abundant copper/O2 catalyst system, readily available feedstocks, broad substrate scope, good functional group tolerance, exclusive regio- chemoselectivity, high step atom efficiency, which offers an important basis for further construction products that are inaccessible or difficult to prepare existing methods employing catalytic amination strategy.

Language: Английский

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Recent Advances in the Use of 2‐Aminobenzyl Alcohols in the Synthesis of Quinolines, Quinazolines and Other N‐Heterocycles

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(10), P. 2142 - 2164

Published: Jan. 17, 2024

Abstract N‐Heterocyclic compounds, in particular, quinolines and quinazolines are frequently used medicinal chemistry. Therefore, the direct clean synthesis of these valuable scaffolds has been a great interest for many years. 2‐Aminobenzyl alcohols as an alternative reactant instead unstable expensive 2‐aminobenzaldehydes can be construction N‐fused heterocycles including quinolines, quinazolines, oxazines, thiazines, selenazines, imidazoles, diazepines, etc. In this review article, we have discussed recent developments use 2‐aminobenzyl diverse heterocycles.

Language: Английский

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Recent Developments of Transition‐Metal‐Catalyzed Cross‐Coupling of Nitriles and Alcohols

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(32)

Published: Aug. 22, 2024

Abstract Cross‐coupling of nitriles and alcohols offers an environmentally friendly atom‐economical method for the synthesis various valuable compounds. These compounds include α ‐alkylated ‐olefinated nitriles, primary amines, imines, N ‐alkylation amides, ‐heterocycles, δ ‐hydroxynitriles, olefins, etc . Herein, we have reviewed recent developments (from 2013–date) transition‐metal‐catalyzed cross‐coupling alcohols. A number transition metal complexes such as noble metals Ru Ir, well base Mn, Fe, Co, Ni are presented. Moreover, different product types, reaction conditions mechanisms discussed to understand catalyst development.

Language: Английский

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A sustainable oxidative esterification of thiols with alcohols by a cobalt nanocatalyst supported on doped carbon

Green Chemistry, Journal Year: 2018, Volume and Issue: 20(9), P. 1992 - 1997

Published: Jan. 1, 2018

With a newly developed cobalt nanocatalyst using N–SiO₂-doped activated carbon as the support (Co/N–SiO₂–AC), sustainable oxidative esterification of (hetero)aryl and alkyl thiols with alcohols has been developed.

Language: Английский

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