Radical Perfluoroalkylation of Aliphatic Substrates

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(12), P. 7756 - 7794

Published: May 25, 2023

A selection of perfluoroalkylation reactions aliphatic substrates that display methodological and synthetic amplitude will be studied, giving examples their applications mechanistic details. An array approaches for fluoroalkylation are documented; in particular, radical protocols prominent among methods. To effect, addition perfluoroalkyl radicals RF (RF=CnF2n+1, n > 1) to unsaturated organic serve as one the most direct efficacious ways access fluoroalkylated scaffolds. The syntheses perfluoroalkyl-substituted vinyl, alkynyl, allylic compounds; hydro-, iodo-, oxy-perfluoroalkylated alkanes olefins; carbonyl enamides, amides, thioamides, hydrazones; multicomponent studied. While there a number accomplished reports on organofluorination, we aim provide an overview radical-involved substrates, covering from 2018 early 2023, summarized Tables 1–4.

Language: Английский

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Carbonylative transformation of aryl halides and strong bonds via cheap metal catalysts and sustainable technologies

Green Synthesis and Catalysis, Journal Year: 2024, Volume and Issue: 5(4), P. 211 - 269

Published: May 6, 2024

The development of catalytic carbonylation reactions has increased considerably. Although many reviews/chapters/books on have been published, summaries cheap metal-catalyzed aryl halides and other chemical bonds with high dissociation energy C-Y (Y = O, N, H) are still very rare. Focusing green sustainable chemistry, this review summarizes discusses the achievements carbonylative transformations (C(sp2)-X) strong based non-expensive metal catalysts (Co, Mn, Mo, Ni, Fe, Cu), photochemical electrochemical systems developed in recent decades.

Language: Английский

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Palladium-Catalyzed Carbonylative Synthesis of Polycyclic 3,4-Dihydroquinolin-2(1H)-one Scaffolds Containing Perfluoroalkyl and Carbonyl Units

Organic Letters, Journal Year: 2023, Volume and Issue: 25(28), P. 5314 - 5318

Published: July 6, 2023

A palladium-catalyzed one-pot two-step radical mediated carbonylative cyclization of 1,7-enynes with perfluoroalkyl iodides and Mo(CO)6 has been developed for the construction polycyclic 3,4-dihydroquinolin-2(1H)-one scaffolds. This method realizes a facile synthesis various derivatives containing carbonyl units in high yields. Moreover, modifications several bioactive molecules were demonstrated using this protocol.

Language: Английский

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Palladium-Catalyzed Carbonylative Synthesis of Amide-Containing Indolo[2,1-a]isoquinolines from Alkene-Tethered Indoles and Nitroarenes

Organic Letters, Journal Year: 2023, Volume and Issue: 25(5), P. 821 - 825

Published: Jan. 30, 2023

In this new procedure, amide-containing indolo[2,1-a]isoquinoline scaffolds were prepared by palladium-catalyzed carbonylative cyclization of alkene-tethered indoles with nitroarenes. By using Mo(CO)6 as the CO source and reductant nitroarenes nitrogen source, reaction produced various derivatives in good yields general. Furthermore, late-stage modifications bioactive molecules protocol demonstrated well.

Language: Английский

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Metal-free synthesis of carbamoylated dihydroquinolinones via cascade radical annulation of cinnamamides with oxamic acids

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(9), P. 1821 - 1833

Published: Jan. 1, 2024

Metal-free synthesis of medicinally important carbamoylated dihydroquinolinones using readily available, cheap and environment-friendly materials with good to excellent yields.

Language: Английский

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Difunctionalization of Dienes, Enynes and Related Compounds via Sequential Radical Addition and Cyclization Reactions

Molecules, Journal Year: 2023, Volume and Issue: 28(3), P. 1145 - 1145

Published: Jan. 23, 2023

Radical reactions are powerful in creating carbon–carbon and carbon–heteroatom bonds. Designing one-pot radical with cascade transformations to assemble the cyclic skeletons two new functional groups is both synthetically operationally efficient. Summarized this paper recent development of involving addition cyclization dienes, diynes, enynes, as well arene-bridged arene-terminated compounds for preparation difunctionalization compounds. Reactions carried out initiators, transition metal-catalysis, photoredox, electrochemical conditions included.

Language: Английский

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Recent Advances for the Synthesis of Dihydroquinolin-2(1H)-ones via Catalytic Annulation of α,β-Unsaturated N-Arylamides

Catalysts, Journal Year: 2023, Volume and Issue: 13(7), P. 1105 - 1105

Published: July 15, 2023

Dihydroquinolin-2(1H)-ones (DHQOs) represent a class of valuable bioactive compounds with six-membered nitrogen-containing heterocyclic structures. The development simple, mild, and efficient synthetic methods has been widely considered by chemists. In this review, we have summarized series different strategies for the synthesis DHQOs via catalytic annulation α,β-unsaturated N-arylamides in past decade, including covering electrophilic cyclization, radical initiated photochemical cyclization reactions. Additionally, substrate scope mechanistic details are also discussed. This paper provides useful reference diverse methodologies DHQO.

Language: Английский

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Recent Advances in the Cascade Cyclization Reactions of 1,7‐Enynes

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 366(3), P. 324 - 356

Published: Dec. 14, 2023

Abstract Elaborated molecular architectures, especially carbocyclic, heterocyclic, endocyclic, and polycyclic structures, serve as an important class of organic complexes because they are frequently occurring core structural units in a variety biologically pharmacologically relevant natural products, drug molecules, agrochemicals, functional materials. A main challenge current synthetic approaches is the development strategically efficient selective formation these compounds from easy‐to‐handle starting The cascade cyclizations 1,7‐enynes have afforded indispensable method for accessing complexity diversity, thus highlighting their potential significance both academic industrial communities. In last decades, tremendous efforts been devoted to discovering convenient routes access sophisticated annulation derivatives, wide range powerful straightforward strategies reported. this review, latest achievements cyclization reactions summarized, which could be separated into three categories: (1) Visible‐light‐induced 1,7‐enynes; (2) Metal‐free catalyzed (3) Transition‐metal‐catalyzed 1,7‐enynes.

Language: Английский

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Photocatalytic, α-Aminoalkyl Radical-Mediated, Methylene-Extrusive Ring-Closing Transformation of o-Alkynyl and o-Cyano Acrylamides

Organic Letters, Journal Year: 2024, Volume and Issue: 26(17), P. 3652 - 3656

Published: April 24, 2024

Herein we report a visible-light-induced, α-aminoalkyl radical-mediated cascade reaction of 1,7-enynes that establishes unique ring-closing enyne transformation pathway which occurs with concomitant loss methylene moiety. The radical derived from

Language: Английский

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Palladium-catalyzed carbonylation of activated alkyl halides via radical intermediates

Industrial Chemistry and Materials, Journal Year: 2023, Volume and Issue: 2(2), P. 276 - 283

Published: Aug. 16, 2023

In this review, we summarize and discuss recent achievements in palladium-catalyzed carbonylative reactions of activated alkyl halides. Aliphatic carboxylic acid derivates were prepared effectively with various nucleophiles.

Language: Английский

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