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

Complementary Oxidative Generation of Iminyl Radicals from α-Imino-oxy Acids: Silver-Catalyzed C–H Cyanoalkylation of Heterocycles and Quinones

(2020) Xiaoqing Li et al.   JOURNAL OF ORGANIC CHEMISTRY

O-Perfluoropyridin-4-yl Oximes: Iminyl Radical Precursors for Photo- or Thermal-Induced N–O Cleavage in C(sp2)–C(sp3) Bond Formation

(2020) Peng-Ju Xia et al.   JOURNAL OF ORGANIC CHEMISTRY

Metal-Free sp3 C-SCF3 Coupling Reactions between Cycloketone Oxime Esters and S-trifluoromethyl 4-Methylbenzenesulfonothioate

(2020) Xia Zhao et al.   ORGANIC LETTERS

Iminyl-Radical-Triggered C–C Bond Cleavage of Cycloketone Oxime Derivatives: Generation of Distal Cyano-Substituted Alkyl Radicals and Their Functionalization

(2020) Tiebo Xiao et al.   SYNTHESIS-STUTTGART

Functionalization of remote C(sp3)-H bonds enabled by copper-catalyzed coupling of O-acyloximes with terminal alkynes

(2020) Zhaodong Li et al.   Nature Communications

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

(2020) Xiao-Ye Yu et al.   ACCOUNTS OF CHEMICAL RESEARCH

Iron‐Mediated Cyanoalkylsulfonylation/Arylation of Active Alkenes with Cycloketone Oxime Derivatives via Sulfur Dioxide Insertion

(2020) Zan Chen et al.   ADVANCED SYNTHESIS & CATALYSIS

Visible-Light-Driven Copper-Catalyzed C(sp3)–O Cross-Coupling of Benzylic Radicals with Phenols

(2020) Xiao-Ye Yu et al.   ORGANIC LETTERS

Directed Cobalt-Catalyzed anti-Markovnikov Hydroalkylation of Unactivated Alkenes Enabled by “Co–H” Catalysis

(2020) Dandan Yang et al.   ORGANIC LETTERS

Directing-Group-Based Strategy Enabling Intermolecular Heck-Type Reaction of Cycloketone Oxime Esters and Unactivated Alkenes

(2020) Yi Deng et al.   ORGANIC LETTERS

Copper-Catalyzed Radical C-C Bond Cleavage and [4+1] Annulation Cascade of Cycloketone Oxime Esters with Enaminothiones

(2019) Yuan He et al.   JOURNAL OF ORGANIC CHEMISTRY

Synthesis of gem-Difluoroalkenes by Merging Ni-Catalyzed C–F and C–C Bond Activation in Cross-Electrophile Coupling

(2019) Decai Ding et al.   ORGANIC LETTERS

Vinylboron Self-Promoted Carbonylative Coupling with Cyclobutanone Oxime Esters

(2019) Zhiping Yin et al.   ORGANIC LETTERS

Photoredox- or Metal-Catalyzed in Situ SO2-Capture Reactions: Synthesis of β-Ketosulfones and Allylsulfones

(2019) Min Zheng et al.   ORGANIC LETTERS

Transition‐Metal‐Promoted Direct C‐H Cyanoalkylation and Cyanoalkoxylation of Internal Alkenes via Radical C‐C Bond Cleavage of Cycloketone Oxime Esters

(2019) Jiang Lou et al.   ADVANCED SYNTHESIS & CATALYSIS

Minisci-Type C-H Cyanoalkylation of Heteroarenes Through N-O/C-C Bonds Cleavage

(2019) Yong Jian et al.   EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Visible-Light-Promoted Redox Neutral γ,γ-Difluoroallylation of Cycloketone Oxime Ethers with Trifluoromethyl Alkenes via C–C and C–F Bond Cleavage

(2019) Yuwei He et al.   ORGANIC LETTERS

Photoinduced, Copper-Catalyzed Radical Cross-Coupling of Cycloketone Oxime Esters, Alkenes, and Terminal Alkynes

(2019) Jun Chen et al.   ORGANIC LETTERS

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

(2019) Peng-Ju Xia et al.   ORGANIC LETTERS

Copper-Catalyzed Cyanoalkylation of Amines via C–C Bond Cleavage: An Approach for C(sp3)–N Bond Formations

(2019) Lin Yang et al.   JOURNAL OF ORGANIC CHEMISTRY

Single-Electron-Transfer-Induced C(sp3)-N Couplings via C-C Bond Cleavage of Cycloketoxime Esters

(2019) Binlin Zhao et al.   JOURNAL OF ORGANIC CHEMISTRY

Photoredox-Catalyzed Sulfonylation of O-Acyl Oximes via Iminyl Radicals with the Insertion of Sulfur Dioxide

(2019) Jun Zhang et al.   ORGANIC LETTERS

Copper-Catalyzed Ring-Opening Radical Trifluoromethylation of Cycloalkanone Oximes

(2019) Zhonglin Liu et al.   ORGANIC LETTERS

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

(2019) Yu-Qi Tang et al.   ORGANIC LETTERS

Copper‐Catalyzed Radical Cross‐Coupling of Oxime Esters and Sulfinates for Synthesis of Cyanoalkylated Sulfones

(2019) Xue-Song Zhou et al.   ChemCatChem

Radical C–C Bond Cleavage/Addition Cascade of Benzyl Cycloketone Oxime Ethers Enabled by Photogenerated Cyclic Iminyl Radicals

(2019) Peng-Zi Wang et al.   ORGANIC LETTERS

Divergent Nickel-Catalysed Ring-Opening–Functionalisation of Cyclobutanone Oximes with Organozincs

(2019) Lucrezia Angelini et al.   SYNLETT

Visible-light-driven cyanoalkylation of quinoxalinones using cyclobutanone oxime esters as the radical precursors

(2019) Bin Zhao et al.   TETRAHEDRON LETTERS

Photoinduced Copper-Catalyzed Radical Aminocarbonylation of Cycloketone Oxime Esters

(2019) Bin Lu et al.   ACS Catalysis

Cu‐Catalyzed Selective Oxy‐Cyanoalkylation of Allylamines with Cycloketone Oxime Esters and CO 2

(2019) Chuan‐Kun Ran et al.   CHINESE JOURNAL OF CHEMISTRY

Nickel-Catalyzed Thiolation and Selenylation of Cycloketone Oxime Esters with Thiosulfonate or Seleniumsulfonate

(2019) Jian Li et al.   JOURNAL OF ORGANIC CHEMISTRY

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

(2019) Jiang-Xi Yu et al.   ORGANIC LETTERS

Enantioselective Radical Ring-Opening Cyanation of Oxime Esters by Dual Photoredox and Copper Catalysis

(2019) Jun Chen et al.   ORGANIC LETTERS

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

(2019) Tao Wang et al.   Nature Communications

Hydroxylamine Derivatives as Nitrogen-Radical Precursors in Visible-Light Photochemistry

(2018) Jacob Davies et al.   CHEMISTRY-A EUROPEAN JOURNAL

Redox-Neutral Cyanoalkylation/Cyclization of Olefinic 1,3-Dicarbonyls with Cycloketone Oxime Esters: Access to Cyanoalkylated Dihydrofurans

(2018) Jia-Yu Zhang et al.   JOURNAL OF ORGANIC CHEMISTRY

Double Dehydrogenation of Primary Amines to Nitriles by a Ruthenium Complex Featuring Pyrazole Functionality

(2018) Indranil Dutta et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Cu-Catalyzed Redox-Neutral Ring Cleavage of Cycloketone O-Acyl Oximes: Chemodivergent Access to Distal Oxygenated Nitriles

(2018) Wenying Ai et al.   ORGANIC LETTERS

Direct C–H Cyanoalkylation of Quinoxalin-2(1H)-ones via Radical C–C Bond Cleavage

(2018) Lin Yang et al.   ORGANIC LETTERS

Iron-Catalyzed Decarboxylative Olefination of Cycloketone Oxime Esters with α,β-Unsaturated Carboxylic Acids via C–C Bond Cleavage

(2018) Jing-Feng Zhao et al.   ORGANIC LETTERS

Fine-tuned organic photoredox catalysts for fragmentation-alkynylation cascades of cyclic oxime ethers

(2018) Franck Le Vaillant et al.   Chemical Science

Bioinspired Synthesis of Nitriles from Primary Amides via Zinc/Anhydride Catalysis

(2018) Yuanyuan Wang et al.   Asian Journal of Organic Chemistry

Iron-Catalyzed Ring-Opening/Allylation of Cyclobutanone Oxime Esters with Allylic Sulfones

(2018) Jing-Feng Zhao et al.   ADVANCED SYNTHESIS & CATALYSIS

Photocatalytic Neophyl Rearrangement and Reduction of Distal Carbon Radicals by Iminyl Radical-Mediated C−C Bond Cleavage

(2018) Xiao-Ye Yu et al.   ADVANCED SYNTHESIS & CATALYSIS

Copper-catalyzed tandem aerobic oxidative cyclization for the synthesis of 4-cyanoalkylpyrrolo[1,2-a]quinoxalines from 1-(2-aminophenyl)pyrroles and cyclobutanone oxime esters

(2018) Zhenyu An et al.   CHEMICAL COMMUNICATIONS

A photocatalytic iminyl radical-mediated C–C bond cleavage/addition/cyclization cascade for the synthesis of 1,2,3,4-tetrahydrophenanthrenes

(2018) Peng-Zi Wang et al.   CHEMICAL COMMUNICATIONS

Photoinduced C-C Bond Cleavage and Oxidation of Cycloketoxime Esters

(2018) Binlin Zhao et al.   CHINESE JOURNAL OF CHEMISTRY

Photoredox-Catalyzed Intermolecular Remote C–H and C–C Vinylation via Iminyl Radicals

(2018) Xu Shen et al.   ORGANIC LETTERS

Photoinduced fragmentation-rearrangement sequence of cycloketoxime esters

(2018) Binlin Zhao et al.   Organic Chemistry Frontiers

Copper-Catalyzed Radical Cross-Coupling of Redox-Active Oxime Esters, Styrenes, and Boronic Acids

(2018) Xiao-Ye Yu et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Copper-Catalyzed Coupling Reactions of Cyclobutanone Oxime Esters with Sulfur Nucleophiles at Room Temperature

(2018) Mingchuang He et al.   JOURNAL OF ORGANIC CHEMISTRY

Gallic Acid-Promoted SET Process for Cyclobutanone Oximes Activation and (Carbonylative-)Alkylation of Olefins

(2018) Zhiping Yin et al.   ACS Catalysis

Nickel-Catalyzed Reductive Electrophilic Ring Opening of Cycloketone Oxime Esters with Aroyl Chlorides

(2018) Decai Ding et al.   ACS Catalysis

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

(2017) Jun Wu et al.   JOURNAL OF ORGANIC CHEMISTRY

Direct C–H Cyanoalkylation of Heteroaromatic N-Oxides and Quinones via C–C Bond Cleavage of Cyclobutanone Oximes

(2017) Yu-Rui Gu et al.   ORGANIC LETTERS

Oxidative 1,2-carboamination of alkenes with alkyl nitriles and amines toward γ-amino alkyl nitriles

(2017) Yan-Yun Liu et al.   Nature Communications

Recent Advances in Radical-Initiated C(sp3)–H Bond Oxidative Functionalization of Alkyl Nitriles

(2017) Xue-Qiang Chu et al.   ACS Catalysis

Catalytic reversible alkene-nitrile interconversion through controllable transfer hydrocyanation

(2016) X. Fang et al.   SCIENCE

Enantioselective cyanation of benzylic C–H bonds via copper-catalyzed radical relay

(2016) Wen Zhang et al.   SCIENCE

Tin or gallium-catalyzed cyanide-transition metal-free synthesis of nitriles from aldehydes or oximes

(2016) Yan-Jun Zhuang et al.   TETRAHEDRON LETTERS

The Mechanism of Acceptorless Amine Double Dehydrogenation by N,N,N-Amide Ruthenium(II) Hydrides: A Combined Experimental and Computational Study

(2016) Lillian V. A. Hale et al.   ACS Catalysis

Copper-Catalyzed Cyanomethylation of Allylic Alcohols with Concomitant 1,2-Aryl Migration: Efficient Synthesis of Functionalized Ketones Containing an α-Quaternary Center

(2015) Ala Bunescu et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Cyanoalkylation: Alkylnitriles in Catalytic CC Bond-Forming Reactions

(2015) Rosa López et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

A radical anti-Markovnikov addition of alkyl nitriles to simple alkenes via selective sp3 C–H bond functionalization

(2015) Zejiang Li et al.   CHEMICAL COMMUNICATIONS

Oxidative radical 1,2-alkylarylation of alkenes with α-C(sp3)–H bonds of acetonitriles involving 1,2-aryl migration

(2015) Yang Li et al.   CHEMICAL COMMUNICATIONS

Direct Synthesis of Nitriles from Aldehydes Using an O-Benzoyl Hydroxylamine (BHA) as the Nitrogen Source

(2015) Xiao-De An et al.   ORGANIC LETTERS

Selective Carbon-Carbon Bond Cleavage for the Stereoselective Synthesis of Acyclic Systems

(2014) Ilan Marek et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

“Nanorust”-catalyzed Benign Oxidation of Amines for Selective Synthesis of Nitriles

(2014) Rajenahally V. Jagadeesh et al.   ChemSusChem

Organoselenium-Catalyzed Mild Dehydration of Aldoximes: An Unexpected Practical Method for Organonitrile Synthesis

(2014) Lei Yu et al.   ORGANIC LETTERS

Oxidant-Free Conversion of Primary Amines to Nitriles

(2013) Kuei-Nin T. Tseng et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Nitrile-Containing Pharmaceuticals: Efficacious Roles of the Nitrile Pharmacophore

(2010) Fraser F. Fleming et al.   JOURNAL OF MEDICINAL CHEMISTRY