☆ 4.6 Review

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

MOLECULES (2023)

相关参考文献

注意：仅列出部分参考文献，下载原文获取全部文献信息。

Review Chemistry, Multidisciplinary

Metallaphotoredox: The Merger of Photoredox and Transition Metal Catalysis

Amy Y. Chan et al.

Summary: The merger of photoredox catalysis with transition metal catalysis, known as metallaphotoredox catalysis, has become an important part of synthetic methodology. It combines the bond formation capability of transition metal catalysis with the utility of photoinduced electron and energy transfer processes. Photocatalytic substrate activation allows the involvement of simple starting materials in metal-mediated bond-forming processes, while electron or energy transfer with organometallic intermediates provides a complementary activation mode to traditional catalytic platforms.

CHEMICAL REVIEWS (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Nickel Catalysis via SH2 Homolytic Substitution: The Double Decarboxylative Cross-Coupling of Aliphatic Acids

Artem Tsymbal et al.

Summary: In this study, a dual photo/nickel catalytic manifold was described, which includes a complementary sequence involving free radical generation, radical sorting via selective binding to a Ni(II) center, and bimolecular homolytic substitution (S(H)2) at a high-valent nickel-alkyl complex. This catalytic manifold enables the elusive cross-coupling of diverse aliphatic carboxylic acids to generate valuable C(sp(3))-C(sp(3))-products. The discovery provides important insights for addressing the long-standing challenge in fragment coupling chemistry.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Article Chemistry, Organic

Pd-Catalyzed C-O Bond Formation Enabling the Synthesis of Congested N,N,O-Trisubstituted Hydroxylamines

Jiaxing Chen et al.

Summary: A Pd-catalyzed C-O cross-coupling reaction was reported, which allows for the synthesis of highly congested hydroxylamines with an α-quaternary carbon center without cleavage of the N-O bond. This strategy shows high chemoselectivity, broad substrate scope, and excellent functional group tolerance, and has been demonstrated by pharmaceutical derivatization and postcatalytic modifications.

ORGANIC LETTERS (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantioselective Reductive N-Cyclization-Alkylation Reaction of Alkene-Tethered Oxime Esters and Alkyl Iodides by Nickel Catalysis

Xue-Gong Jia et al.

Summary: This study reports a novel N-cyclization-alkylation reaction, showcasing the potential of heterocyclization for accessing enantioenriched cyclic architectures and solving a long-standing challenge in synthetic chemistry.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Review Chemistry, Organic

N-Alkoxyphtalimides as Versatile Alkoxy Radical Precursors in Modern Organic Synthesis

Alexander S. Budnikov et al.

Summary: O-substituted derivatives of N-hydroxyphthalimide (NHPI) have gained attention as convenient reagents for generating free radicals under mild conditions. N-alkoxyphtalimides are effective in generating alkoxy free radicals, leading to selective synthetic transformations. This review discusses visible light induced reactions, including hydrogen atom transfer and beta-scission, as well as non-photochemical tin-mediated processes.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2022)

添加到收藏夹

Article Chemistry, Organic

Ni and Fe catalyzed cascade radical reactions of oxime esters with diselenides

Linpeng Liu et al.

Summary: A method for radical cyclization and ring-opening of oxime esters with diselenides has been developed. Both Ni(0) and Fe(ii) catalysts can be used for the selenylation of olefin-containing and cyclic oxime ester derivatives. Using this method, a variety of functionalized pyrrolines and alkyl nitriles can be synthesized in good yields. Additionally, a mechanism involving iminyl radical and carbon-centered radical intermediates has been proposed.

ORGANIC CHEMISTRY FRONTIERS (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantioselective Reductive N-Cyclization-Alkylation Reaction of Alkene-Tethered Oxime Esters and Alkyl Iodides by Nickel Catalysis

Xue-Gong Jia et al.

Summary: This study presents a new method for the preparation of enantioenriched heterocycles through N-cyclization-alkylation reaction, addressing a long-standing challenge in the synthetic community and achieving highly enantioenriched pyrrolines under mild conditions.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Review Chemistry, Applied

Recent Developments in Radical Cross-Coupling of Redox-Active Cycloketone Oximes

Fang Xiao et al.

Summary: A new method has been discovered to introduce active cyanoalkyl groups into organic compounds via ring fragmentation without the use of toxic cyanide sources. Recent advances in redox-active cycloketone oximes-based cross-couplings were comprehensively reviewed, categorizing into non-photocatalyzed and photocatalyzed cross-couplings with representative examples and reaction mechanisms discussed.

ADVANCED SYNTHESIS & CATALYSIS (2021)

添加到收藏夹

Article Chemistry, Applied

[3+1+1] Annulation Reaction of Benzo-1,2-Quinones, Aldehydes and Hydroxylamine Hydrochloride: Access to Benzoxazoles with Inorganic Nitrogen Source

Fulin Chen et al.

Summary: The synthesis of benzoxazoles using inorganic hydroxylamine hydrochloride as the nitrogen source in a [3+1+1] annulation reaction with benzo-1,2-quinones and aldehydes was reported, resulting in high yields of various useful benzoxazoles. Preliminary mechanistic studies indicated that the quinone oxime serves as the reaction intermediate instead of the aldehyde oxime.

ADVANCED SYNTHESIS & CATALYSIS (2021)

添加到收藏夹

Article Chemistry, Organic

Chemodivergent Synthesis of Oxazoles and Oxime Ethers Initiated by Selective C-N/C-O Formation of Oximes and Diazo Esters

Zhenjie Qi et al.

Summary: Chemodivergent reactions of oximes and diazo esters involving Rh-catalyzed [3+2] annulation and photodriven O-H insertion have been developed to generate oxazoles and oxime ethers, showing excellent tolerance to a variety of functional groups.

ORGANIC LETTERS (2021)

添加到收藏夹

Review Chemistry, Applied

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

Igor B. Krylov et al.

Summary: This review focuses on synthetic methods based on oxime-derived iminyl radicals developed in the last few years, excluding ring opening reactions of cyclic iminyl radicals summarized in recent publications. It highlights reactions involving 1,n-hydrogen atom transfer and addition of iminyl radicals to the carbon-carbon pi-bond, showcasing the versatility and utility of these methods in organic synthesis.

ADVANCED SYNTHESIS & CATALYSIS (2021)

添加到收藏夹

Review Chemistry, Applied

Radical Cascade Reactions of β,γ-Unsaturated Hydrazones/Oximes

Ya-Feng Si et al.

Summary: This review summarizes and classifies three catalytic ways of radical cascade cyclization of beta,gamma-unsaturated hydrazones/oximes: transition-metal-catalyzed systems, transition-metal-free systems, and photo-/electrocatalytic systems. Through these methods, various functional groups are installed on the pyrazoline and isoxazoline skeletons to enrich the small organic molecule library.

ADVANCED SYNTHESIS & CATALYSIS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Photoinduced Copper-Catalyzed Asymmetric C-O Cross-Coupling

Jun Chen et al.

Summary: This study presents a photoinduced copper-catalyzed cross-coupling reaction for the generation of allylic esters. The reaction proceeds at room temperature with high regio- and enantioselectivity.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

添加到收藏夹

Article Chemistry, Organic

Copper-Catalyzed β-Lactam Formation Initiated by 1,3-Azaprotio Transfer of Oximes and Methyl Propiolate

Zhenjie Qi et al.

Summary: A copper(II)-catalyzed protocol has been developed for the construction of trans-configured beta-lactams and spirocyclic beta-lactams from oximes and methyl propiolate, with excellent substrate flexibility and diastereoselectivity (up to >99:1 dr). In situ FT-IR mechanistic experiments suggest that ketene species may be involved in the formation of beta-lactams.

ORGANIC LETTERS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Iron(ii)-catalyzed intermolecular aziridination of alkenes employing hydroxylamine derivatives as clean nitrene sources

Georgina Kirby et al.

Summary: The iron-catalyzed intermolecular aziridination of alkenes with hydroxylamine derivatives was successfully achieved by using simple methods to synthesize a variety of aziridines. The sustainable reaction conditions allowed for high yields of products to be obtained. Preliminary mechanistic studies suggest the operation of both concerted and stepwise pathways in this transformation.

GREEN CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Rhodium(iii)-catalyzed asymmetric [4+1] spiroannulations of O-pivaloyl oximes with α-diazo compounds

Lincong Sun et al.

Summary: The asymmetric [4+1] spiroannulation of O-pivaloyl oximes with alpha-diazo homophthalimides catalyzed by chiral Rh-III catalysts results in the formation of chiral spirocyclic imines through C-H activation and N-O cleavage under redox-neutral and acid/base-neutral conditions. This reaction is highly efficient and shows broad substrate scope, mild reaction conditions, and high to excellent enantioselectivities.

CHEMICAL COMMUNICATIONS (2021)

添加到收藏夹

Article Chemistry, Organic

Visible-Light Photoredox-Catalyzed Regioselective Sulfonylation of Alkenes Assisted by Oximes via [1,5]-H Migration

Shichao Yang et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

添加到收藏夹

Review Chemistry, Multidisciplinary

When Light Meets Nitrogen-Centered Radicals: From Reagents to Catalysts

Xiao-Ye Yu et al.

ACCOUNTS OF CHEMICAL RESEARCH (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Hydroxylamines As Bifunctional Single-Nitrogen Sources for the Rapid Assembly of Diverse Tricyclic Indole Scaffolds

Liangxin Fan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

添加到收藏夹

Article Chemistry, Organic

Copper-Catalyzed Annulation of Oxime Acetates with α-Amino Acid Ester Derivatives: Synthesis of 3-Sulfonamido/Imino 4-Pyrrolin-2-ones

Chun-Bao Miao et al.

ORGANIC LETTERS (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Iron-Catalyzed, Iminyl Radical-Triggered Cascade 1,5-Hydrogen Atom Transfer/(5+2) or (5+1) Annulation: Oxime as a Five-Atom Assembling Unit

Wu Liang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

添加到收藏夹

Review Chemistry, Multidisciplinary

Recent advances for the photoinduced C-C bond cleavage of cycloketone oximes

Wei Xiao et al.

CHINESE CHEMICAL LETTERS (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Iron-catalyzed carbonylative cyclization of γ,δ-unsaturated aromatic oxime esters with amines

Youcan Zhang et al.

CHEMICAL COMMUNICATIONS (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Ruthenium-catalyzed cascade C-H activation/annulation of N-alkoxybenzamides: reaction development and mechanistic insight

Liangliang Song et al.

CHEMICAL SCIENCE (2020)

添加到收藏夹

Article Chemistry, Organic

Copper-catalyzed borylative cyclization of γ,δ-unsaturated aromatic oxime esters to (borylmethyl)pyrrolidines

Youcan Zhang et al.

ORGANIC CHEMISTRY FRONTIERS (2020)

添加到收藏夹

Review Chemistry, Multidisciplinary

Synthesis and Transformations of Nitrones for Organic Synthesis

Shun-Ichi Murahashi et al.

CHEMICAL REVIEWS (2019)

添加到收藏夹

Article Chemistry, Organic

Copper-Catalyzed Dihydroquinolinone Synthesis from isocyanides and O-Benzoyl Hydroxylamines

Zhen Yang et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

添加到收藏夹

Article Chemistry, Physical

4-HO-TEMPO-Catalyzed Redox Annulation of Cyclopropanols with Oxime Acetates toward Pyridine Derivatives

Jun-Long Zhan et al.

ACS CATALYSIS (2019)

添加到收藏夹

Article Chemistry, Organic

Photocatalytic, Phosphoranyl Radical-Mediated N-O Cleavage of Strained Cycloketone Oximes

Peng-Ju Xia et al.

ORGANIC LETTERS (2019)

添加到收藏夹

Article Chemistry, Organic

Ni-Catalyzed Redox-Neutral Ring-Opening/Radical Addition/Ring-Closing Cascade of Cycloketone Oxime Esters and Vinyl Azides

Yu-Qi Tang et al.

ORGANIC LETTERS (2019)

添加到收藏夹

Article Chemistry, Organic

One-Carbon Incorporation Using Cyclobutanone Oxime Ester Enabled [2+2+1] Carboannulation of 1,7-Enynes by C-C/N-O Bond Cleavage and C-H Functionalization

Jiang-Xi Yu et al.

ORGANIC LETTERS (2019)

添加到收藏夹

Article Multidisciplinary Sciences

Enantioselective cyanation via radical-mediated C-C single bond cleavage for synthesis of chiral dinitriles

Tao Wang et al.

NATURE COMMUNICATIONS (2019)

添加到收藏夹

Article Chemistry, Organic

Iminyl radical-promoted imino sulfonylation, imino cyanogenation and imino thiocyanation of γ,δ-unsaturated oxime esters: synthesis of versatile functionalized pyrrolines

Yuebo Wang et al.

ORGANIC CHEMISTRY FRONTIERS (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Transition-metal free C-C bond cleavage/borylation of cycloketone oxime esters

Jin-Jiang Zhang et al.

CHEMICAL SCIENCE (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

A copper-catalyzed diastereoselective O-transfer reaction of N-vinyl-α,β-unsaturated nitrones with ketenes into γ-lactones through [5+2] cycloaddition and N-O bond cleavage

Jun-Yi Liao et al.

GREEN CHEMISTRY (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Silver-promoted cascade radical cyclization of γ,δ-unsaturated oxime esters with P(O)H compounds: synthesis of phosphorylated pyrrolines

Chen Chen et al.

CHEMICAL COMMUNICATIONS (2019)

添加到收藏夹

Article Chemistry, Organic

Contrasting C- and O-Atom Reactivities of Neutral Ketone and Enolate Forms of 3-Sulfonyloxyimino-2-methyl-1-phenyl-1-butanones

Yingtang Ning et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

添加到收藏夹

Article Chemistry, Organic

Copper-Catalyzed Redox-Neutral Cyanoalkylarylation of Activated Alkenes with Cyclobutanone Oxime Esters

Jun Wu et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Redox-Divergent Synthesis of Fluoroalkylated Pyridines and 2-Pyridones through Cu-Catalyzed N-O Cleavage of Oxime Acetates

Dachang Bai et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Copper-catalyzed synthesis of thiazol-2-yl ethers from oxime acetates and xanthates under redox-neutral conditions

Zhongzhi Zhu et al.

CHEMICAL COMMUNICATIONS (2018)

添加到收藏夹

Article Chemistry, Organic

Modular 2,3-diaryl-2H-azirine synthesis from ketoxime acetates via Cs2CO3-mediated cyclization

Mi-Na Zhao et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2018)

添加到收藏夹

Article Chemistry, Organic

Redox-Neutral Access to Isoquinolinones via Rhodium(III)-Catalyzed Annulations of O-Pivaloyl Oximes with Ketenes

Xifa Yang et al.

ORGANIC LETTERS (2018)

添加到收藏夹

Article Chemistry, Organic

Facile construction of trifluoromethyl-azirines via one-pot metal-free Neber reaction

Yin-Jun Huang et al.

TETRAHEDRON (2018)

添加到收藏夹

Review Chemistry, Multidisciplinary

Copper-Catalyzed Radical Relay for Asymmetric Radical Transformations

Fei Wang et al.

ACCOUNTS OF CHEMICAL RESEARCH (2018)

添加到收藏夹

Article Chemistry, Organic

Direct N-H/N-Me Aziridination of Unactivated Olefins Using O-(Sulfonyl)hydroxylamines as Aminating Agents

Shekh Sabir et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Stereospecific Alkene Aziridination Using a Bifunctional Amino-Reagent: An Aza-Prilezhaev Reaction

Joshua J. Farndon et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Construction of 2,3-quaternary fused indolines from alkynyl tethered oximes and diaryliodonium salts through a cascade strategy of N-arylation/cycloaddition/[3,3]-rearrangement

Xiao-Pan Ma et al.

GREEN CHEMISTRY (2017)

添加到收藏夹

Article Chemistry, Organic

K2CO3-Mediated Cyclization and Rearrangement of γ,δ-Alkynyl Oximes To Form Pyridols

Shun Wang et al.

ORGANIC LETTERS (2017)

添加到收藏夹

Article Chemistry, Organic

Iron-Catalyzed Synthesis of 2H-Imidazoles from Oxime Acetates and Vinyl Azides under Redox-Neutral Conditions

Zhongzhi Zhu et al.

ORGANIC LETTERS (2017)

添加到收藏夹

Article Chemistry, Physical

Nickel-Catalyzed 1,2-Aminoarylation of Oxime Ester-Tethered Alkenes with Boronic Acids

Hai-Bin Yang et al.

ACS CATALYSIS (2017)

添加到收藏夹

Article Chemistry, Physical

Copper-Catalyzed Intermolecular Cyclization between Oximes and Alkenes: A Facile Access to Spiropyrrolines

Bo Zhao et al.

ACS CATALYSIS (2017)

添加到收藏夹

Article Chemistry, Organic

Palladium-catalyzed C(sp2)-H aminoimidoylation of isocyano-containing arenes: synthesis of amino substituted N-heterocycles

Zhuang Xiong et al.

ORGANIC CHEMISTRY FRONTIERS (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Nucleophilic Arylation of N,O-Ketene Acetals with Triaryl Aluminum Reagents: Access to α-Aryl Amides through an Umpolung Process

Norihiko Takeda et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

添加到收藏夹

Review Chemistry, Multidisciplinary

Metal-Involving Synthesis and Reactions of Oximes

Dmitrii S. Bolotin et al.

CHEMICAL REVIEWS (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Iron-catalyzed synthesis of benzoxazoles by oxidative coupling/cyclization of phenol derivatives with benzoyl aldehyde oximes

Sen Gao et al.

CHEMICAL COMMUNICATIONS (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Synthesis of Highly Substituted Pyridines through Copper-Catalyzed Condensation of Oximes and α,β-Unsaturated Imines

Wei Wen Tan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

添加到收藏夹

Review Chemistry, Applied

Transition Metal-Catalyzed Reactions Involving Oximes

Jun Li et al.

ADVANCED SYNTHESIS & CATALYSIS (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Internal Oxidant-Triggered Aerobic Oxygenation and Cyclization of Indoles under Copper Catalysis

Huawen Huang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

添加到收藏夹

Article Chemistry, Applied

The Reactivity of Difluorocarbene with Hydroxylamines: Synthesis of Carbamoyl Fluorides

Hannah Baars et al.

ADVANCED SYNTHESIS & CATALYSIS (2016)

添加到收藏夹

Review Chemistry, Multidisciplinary

Visible light photoredox-controlled reactions of N-radicals and radical ions

Jia-Rong Chen et al.

CHEMICAL SOCIETY REVIEWS (2016)

添加到收藏夹

Article Chemistry, Organic

Metal-Free Assembly of Polysubstituted Pyridines from Oximes and Acroleins

Huawen Huang et al.

JOURNAL OF ORGANIC CHEMISTRY (2016)

添加到收藏夹

Article Chemistry, Organic

Synthesis of Polyfunctional Pyridines via Copper-Catalyzed Oxidative Coupling Reactions

Yajie Fu et al.

JOURNAL OF ORGANIC CHEMISTRY (2016)

添加到收藏夹

Article Chemistry, Organic

The organocatalytic asymmetric Neber reaction for the enantioselective synthesis of spirooxindole 2H-azirines

Jian-Qiang Zhao et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2016)

添加到收藏夹

Review Chemistry, Medicinal

Radical Addition-Initiated Domino Reactions of Conjugated Oxime Ethers

Masafumi Ueda

CHEMICAL & PHARMACEUTICAL BULLETIN (2014)

添加到收藏夹

Review Chemistry, Multidisciplinary

Rearrangement of N-Oxyenamines and Related Reactions

Andrey A. Tabolin et al.

CHEMICAL REVIEWS (2014)

添加到收藏夹

Article Chemistry, Multidisciplinary

An efficient synthesis of polysubstituted pyrroles via copper-catalyzed coupling of oxime acetates with dialkyl acetylenedicarboxylates under aerobic conditions

Xiaodong Tang et al.

CHEMICAL COMMUNICATIONS (2013)

添加到收藏夹

Article Chemistry, Organic

Rhodium(III)-Catalyzed Cyclization Olefination of N-Acetoxyl Ketoimine-Alkynes

Peng Zhao et al.

ORGANIC LETTERS (2012)

添加到收藏夹

© Peeref 2019-2024. All rights reserved.