Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(52)

Published: June 28, 2023

Abstract Selenium, originally described as a toxin, turns out to be crucial trace element for life that appears selenocysteine and its dimer, selenocystine. From the point of view drug developments, selenium‐containing drugs are isosteres sulfur oxygen with advantage presence selenium atom confers antioxidant properties high lipophilicity, which would increase cell membrane permeation leading better oral bioavailability. In this article, we have focused on relevant features atom, above all, corresponding synthetic approaches access variety organoselenium molecules along proposed reaction mechanisms. The preparation biological selenosugars, including selenoglycosides, selenonucleosides, selenopeptides, other compounds will treated. We attempted condense most important aspects interesting examples chemistry into single article.

Language: Английский

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Reductive Functionalization of Pyridine-Fused N-Heteroarenes

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

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Beyond Friedel and Crafts: Directed Alkylation of C−H Bonds in Arenes

Angewandte Chemie International Edition, Journal Year: 2018, Volume and Issue: 58(22), P. 7202 - 7236

Published: Aug. 14, 2018

Abstract Alkylation of arenes is one the most fundamental transformations in chemical synthesis and leads to privileged scaffolds many areas science. Classical methods for introduction alkyl groups are mostly based on Friedel–Crafts reaction, radical additions, metalation, or prefunctionalization arene: these methods, however, suffer from limitations scope, efficiency, selectivity. Moreover, they innate reactivity starting arene, favoring alkylation at a certain position rendering chains other positions much more challenging. This can be addressed by use directing group that facilitates, presence metal catalyst, regioselective C−H bond. These directed alkylations bonds will comprehensively summarized this Review.

Language: Английский

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

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

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Beyond Friedel and Crafts: Innate Alkylation of C−H Bonds in Arenes

Angewandte Chemie International Edition, Journal Year: 2018, Volume and Issue: 58(23), P. 7558 - 7598

Published: Aug. 14, 2018

Alkylated arenes are ubiquitous molecules and building blocks commonly utilized in most areas of science. Despite its apparent simplicity, the regioselective alkylation is still a challenging transformation lot cases. Classical methods for introduction alkyl groups to arenes, such as venerable Friedel-Crafts reaction, radical additions, metalation or prefunctionalization arene followed by further alkylation, well alternatives directed C-H bonds, suffer from severe limitations terms scope, efficiency, selectivity. This can be addressed exploiting innate reactivity some (hetero)arenes, which electronic steric properties, governed (or not) presence one multiple) heteroatom(s), ensure high levels regioselectivity. These alkylations bonds (hetero)arenes will overviewed comprehensively this Review.

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

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

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Merrifield resin-supported quinone as an efficient biomimetic catalyst for metal-free, base-free, chemoselective synthesis of 2,4,6-trisubstituted pyridines

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

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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

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

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