Oxime‐Derived Iminyl Radicals in Selective Processes of Hydrogen Atom Transfer and Addition to Carbon‐Carbon π‐Bonds

Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 363(10), P. 2502 - 2528

Published: March 25, 2021

Abstract Oximes represent one of the fundamental organic compound classes with a wide range synthetic applications. In last decade O ‐substituted oximes were recognized as synthetically available and versatile precursors iminyl radicals via one‐electron oxidation or reduction employing visible light photoredox catalysts, salts abundant metals (such Cu Fe), other convenient reagents. Iminyl are powerful synthons for various processes cyclization, ring‐opening, CH‐functionalization, coupling. The present review is focused on methods based oxime‐derived developed in few years excluding ring opening reactions cyclic that summarized recent publications. consists two main parts: (1) involving 1,n‐hydrogen atom transfer (n=5 most cases) (2) addition radical to carbon‐carbon π‐bond. magnified image

Language: Английский

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Synthesis of Diverse 4‐Pyrrolin‐2‐ones by Electrochemically Induced Dehydrogenative Regioselective Cyclization of 3‐Aza‐1,5‐dienes and 1,3‐Dicarbonyl Compounds

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(11)

Published: Jan. 20, 2024

Abstract A practical and mild electrochemical dehydrogenative regioselective cyclization method has been established for the synthesis of 4‐pyrrolin‐2‐ones using 3‐aza‐1,5‐dienes 1,3‐dicarbonyl compounds as substrates. This protocol is catalyst‐free, metal‐free, does not require oxidizing agents. It exhibits wide substrate compatibility can be easily scaled up to gram scale.

Language: Английский

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Copper-Catalyzed Annulation of O-Acyl Oximes with Cyclic 1,3-Diones for the Synthesis of 7,8-Dihydroindolizin-5(6H)-ones and Cyclohexanone-Fused Furans

Organic Letters, Journal Year: 2023, Volume and Issue: 25(5), P. 838 - 842

Published: Jan. 27, 2023

A copper-catalyzed annulation of O-acyl oximes with cyclic 1,3-diones has been developed for the concise synthesis 7,8-dihydroindolizin-5(6H)-ones and cyclohexanone-fused furans through substituent-controlled selective radical coupling process. 2-Alkyl undergo C-C coupling, while 2-unsubstituted C-O coupling.

Language: Английский

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Photoredox/nickel dual-catalysis-enabled synthesis of N-heterocycles from alkyl chlorides and alkenes

Molecular Catalysis, Journal Year: 2024, Volume and Issue: 553, P. 113806 - 113806

Published: Jan. 1, 2024

Language: Английский

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Recent Advances in N-O Bond Cleavage of Oximes and Hydroxylamines to Construct N-Heterocycle

Molecules, Journal Year: 2023, Volume and Issue: 28(4), P. 1775 - 1775

Published: Feb. 13, 2023

Oximes and hydroxylamines are a very important class of skeletons that not only widely exist in natural products drug molecules, but also synthon, which have been used industrial production. Due to weak N-O σ bonds oximes hydroxylamines, they can be easily transformed into other functional groups by bond cleavage. Therefore, the synthesis N-heterocycle using as nitrogen sources has attracted wide attention. Recent advances for through transition-metal-catalyzed radical-mediated cyclization classified type rings summarized. In this paper, recent cleavage reviewed. We hope review provides new perspective on field, reference develop environmentally friendly sustainable methods.

Language: Английский

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One-electron oxidative dehydrogenative annulation and cyclization reactions

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 7(15), P. 2107 - 2144

Published: Jan. 1, 2020

This review focuses on the recent advances in one-electron oxidation involved oxidative dehydrogenative annulations and cyclizations for intermolecular intramolecular construction of valuable ring structures.

Language: Английский

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Synthesis of Stable N–H Imines with a Benzo[7,8]indolizine Core and Benzo[7,8]indolizino[1,2-c]quinolines via Copper-Catalyzed Annulation of α,β-Unsaturated O-Acyl Ketoximes with Isoquinolinium N-Ylides

Organic Letters, Journal Year: 2022, Volume and Issue: 24(21), P. 3828 - 3833

Published: May 23, 2022

A copper-catalyzed annulation of α,β-unsaturated O-acyl ketoximes with isoquinolinium N-ylides has been developed for the concise synthesis stable N-H imines a benzo[7,8]indolizine core. When β-(2-bromoaryl)-α,β-unsaturated are used as starting materials, cascade cyclization occurs to afford benzo[7,8]indolizino[1,2-c]quinolines.

Language: Английский

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Oxime Esters: Flexible Building Blocks for Heterocycle Formation

Topics in Current Chemistry, Journal Year: 2023, Volume and Issue: 381(4)

Published: May 18, 2023

Language: Английский

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Catalytic asymmetric de novo construction of 4-pyrrolin-2-ones via intermolecular formal [3+2] cycloaddition of azoalkenes with azlactones

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(39), P. 5902 - 5905

Published: Jan. 1, 2023

The chiral phosphoric acid-catalyzed asymmetric intermolecular formal [3+2] cycloaddition of azoalkenes with azlactones has been established. This convergent protocol leads to a facile and enantioselective de novo construction wide range fully substituted 4-pyrrolin-2-ones bearing carbon atom in good yields excellent enantioselectivities (26 examples, 72-95% 87-99% ee).

Language: Английский

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Copper-Catalyzed [3 + 2] Annulation of O-Acyl Oximes with 4-Sulfonamidophenols for the Synthesis of 5-Sulfonamidoindoles and 2-Amido-5-sulfonamidobenzofuran-3(2H)-ones

Organic Letters, Journal Year: 2024, Volume and Issue: 26(20), P. 4229 - 4234

Published: May 13, 2024

A copper-catalyzed [3 + 2] annulation of

Language: Английский

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