H-phosphinates, H-phosphonates and secondary phosphine oxides in radical reactions and strategy analysis

Recent Advances in the Construction of Phosphorus‐substituted Heterocycles, 2009‐2019

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

Direct Enamido C(sp 2 )−H Diphosphorylation Enabled by a PCET‐Triggered Double Radical Relay: Access to gem ‐Bisphosphonates

(2020) Hao‐Qiang Cao et al.   CHEMISTRY-A EUROPEAN JOURNAL

Redox-Neutral P(O)–N Coupling between P(O)–H Compounds and Azides via Dual Copper and Photoredox Catalysis

(2020) Yanan Wu et al.   ORGANIC LETTERS

Focusing on the Catalysts of the Pd- and Ni-Catalyzed Hirao Reactions

(2020) György Keglevich et al.   MOLECULES

Phosphorus Compounds as Precursors and Catalysts for Radical C−C Bond‐Forming Reactions

(2020) Jeremy Maddigan‐Wyatt et al.   ADVANCED SYNTHESIS & CATALYSIS

Selective C-H or N-H Imidoylative Annulation of 2-(2-Isocyanophenyl)-1H-indoles Leading to Diverse Indole-fused Scaffolds

(2019) Fan Teng et al.   ADVANCED SYNTHESIS & CATALYSIS

Electrochemical Dehydrogenative Phosphorylation of Alcohols for the Synthesis of Organophosphinates

(2019) Lingling Deng et al.   JOURNAL OF ORGANIC CHEMISTRY

Copper-Catalyzed C4-H Regioselective Phosphorylation/Trifluoromethylation of Free 1-Naphthylamines

(2019) Chunfeng Jing et al.   ORGANIC LETTERS

Microwave-assisted synthesis of phosphonic and phosphinic esters and phosphine oxides by the Hirao reaction

(2019) Réka Henyecz   PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS

Radical Promoted C(sp2)–S Formation and C(sp3)–S Bond Cleavage: Access to 2-Substituted Thiochromones

(2019) Jian Xu et al.   ORGANIC LETTERS

Ceric(IV) Ammonium Nitrate Mediated Phosphorylation of Alkenes: Easy Access to (E )-Vinylphosphonates

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

Electrochemical Dehydrogenative Coupling of Alcohols with Hydrogen Phosphoryl Compounds: A Green Protocol for P−O Bond Formation

(2019) Qian-Yu Li et al.   ADVANCED SYNTHESIS & CATALYSIS

New developments on the Hirao reactions, especially from “green” point of view

(2019) Réka Henyecz et al.   CURRENT ORGANIC SYNTHESIS

Visible-Light Excitation of Quinolinone-Containing Substrates Enables Divergent Radical Cyclizations

(2019) Kiho Kim et al.   ORGANIC LETTERS

Ag-Mediated Radical Cyclization of 2-Alkynylthio(seleno)anisoles: Direct Synthesis of 3-Phosphinoylbenzothio(seleno)phenes

(2019) Tao Cai et al.   ORGANIC LETTERS

Three-Component Chlorophosphinoylation of Alkenes via Anodically Coupled Electrolysis

(2019) Lingxiang Lu et al.   SYNLETT

DDQ-promoted C(sp3) H phosphorylation of cycloheptatriene

(2019) Chunxiao Wen et al.   TETRAHEDRON LETTERS

Visible‐Light‐Promoted Transition‐Metal‐Free Approach toward Phosphoryl‐Substituted Dihydroisoquinolones via Cascade Phosphorylation/Cyclization of N ‐Allylbenzamides

(2019) Xiao‐Ceng Liu et al.   ADVANCED SYNTHESIS & CATALYSIS

Manganese-Catalyzed and Mediated Synthesis of Arylphosphinates and Related Compounds

(2019) Olivier Berger et al.   JOURNAL OF ORGANIC CHEMISTRY

Proton-Coupled Electron Transfer Enables Tandem Radical Relay for Asymmetric Copper-Catalyzed Phosphinoylcyanation of Styrenes

(2019) Guoyu Zhang et al.   ORGANIC LETTERS

Electrochemically Facilitated Oxidative Coupling of Quinoxalin‐2(1 H )‐Ones with Diarylphosphine Oxides and Pyrroles: A Green Protocol for C−P, C−C( sp 2 ) Bond Formation

(2019) Chen Hu et al.   Asian Journal of Organic Chemistry

Scalable Rhodium(III)-Catalyzed Aryl C−H Phosphorylation Enabled by Anodic Oxidation Induced Reductive Elimination

(2019) Zheng-Jian Wu et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Construction of Sulfonyl Phthalides via Copper-Catalyzed Oxysulfonylation of 2-Vinylbenzoic Acids with Sodium Sulfinates

(2019) Yan-Shi Xiong et al.   JOURNAL OF ORGANIC CHEMISTRY

Phosphinoyl radical-initiated vicinal hydroxy-phosphorylation of alkenes

(2019) Adedamola Shoberu et al.   TETRAHEDRON

Mn(III)‐Mediated Regioselective 6‐ endo ‐trig Radical Cyclization of o ‐Vinylaryl Isocyanides to Access 2‐Functionalized Quinolines

(2019) Yan Liu et al.   ADVANCED SYNTHESIS & CATALYSIS

Asymmetric Covalent Triazine Framework for Enhanced Visible-Light Photoredox Catalysis via Energy Transfer Cascade

(2018) Wei Huang et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Phosphenium Cation Mediated Formal Cycloaddition Approach to Benzophospholes

(2018) Masahiro Miura et al.   CHEMISTRY-A EUROPEAN JOURNAL

Transition-Metal-Free C–P Bond Formation via Decarboxylative Phosphorylation of Cinnamic Acids with P(O)H Compounds

(2018) Lixin Liu et al.   JOURNAL OF ORGANIC CHEMISTRY

Bronsted Acid/Organic Photoredox Cooperative Catalysis: Easy Access to Tri- and Tetrasubstituted Alkenylphosphorus Compounds from Alcohols and P–H Species

(2018) Peizhong Xie et al.   ORGANIC LETTERS

Base-Promoted Direct Oxyphosphorylation of Alkynes with H-Phosphine Oxides in the Presence of Water

(2018) Lei Shi et al.   SYNLETT

Direct synthesis of β-ketophosphine oxides via copper-catalyzed difunctionalization of alkenes with H-phosphine oxides and dioxygen

(2018) Guangming Nan et al.   TETRAHEDRON LETTERS

Visible light photoredox-catalyzed phosphorylation of quinoxalin-2(1 H )-ones

(2018) Yubin Kim et al.   TETRAHEDRON LETTERS

Phosphinoyl-functionalization of unactivated alkenes through phosphinoyl radical-triggered distal functional group migration

(2018) Dong Chen et al.   Organic Chemistry Frontiers

Regioselective Silver-Catalyzed Carbon-Phosphorus Difunctionalization of Maleimides: One-Step Construction of Phosphonylated Indolylmaleimides and Pyrrolylmaleimides

(2018) Zhen-Hua Yang et al.   ADVANCED SYNTHESIS & CATALYSIS

DDQ-Promoted Allylic C−H Phosphorylation of 1,3-Diarylpropenes

(2018) Qian Chen et al.   ADVANCED SYNTHESIS & CATALYSIS

Phosphorus Radical-Initiated Cascade Reaction To Access 2-Phosphoryl-Substituted Quinoxalines

(2018) Yan Liu et al.   JOURNAL OF ORGANIC CHEMISTRY

Visible-Light-Induced Organophotoredox Catalyzed Phosphonylation of 2H-Indazoles with Diphenylphosphine Oxide

(2018) Mukta Singsardar et al.   JOURNAL OF ORGANIC CHEMISTRY

Visible Light-Mediated Photocatalytic Metal-Free Cross-Coupling Reaction of Alkenyl Carboxylic Acids with Diarylphosphine Oxides Leading to β-Ketophosphine Oxides

(2018) Hai-Feng Qian et al.   ORGANIC LETTERS

DDQ-mediated direct C(sp3)–H phosphorylation of xanthene derivatives

(2018) Qian Chen et al.   Organic Chemistry Frontiers

Applications of transition metal catalyzed P-radical for synthesis of organophosphorus compounds

(2018) Wei Ren et al.   PURE AND APPLIED CHEMISTRY

K2S2O8-Promoted Direct C-H Phosphorylation of (Benzo)thiazoles

(2017) Weidong Lin et al.   EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Copper-Catalyzed Cascade Phosphorylation Initiated Radical Cyclization: Access to 2-Phosphorylated Pyrrolo[1,2-a]indole

(2017) Honglin Zhang et al.   JOURNAL OF ORGANIC CHEMISTRY

Mn(OAc)3-Promoted Oxidative Csp3–P Bond Formation through Csp2–Csp2 and P–H Bond Cleavage: Access to β-Ketophosphonates

(2017) Pan Zhou et al.   JOURNAL OF ORGANIC CHEMISTRY

Regioselective phosphinylation of coumarins under green LED irradiation and its mechanism

(2017) Qingrui Li et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Cu(i)/Fe(iii)-Catalyzed C–P cross-coupling of styrenes with H-phosphine oxides: a facile and selective synthesis of alkenylphosphine oxides and β-ketophosphonates

(2017) Jian Gu et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Silver-Catalyzed Radical-Involved Cascade Cyclization of Diphenylphosphine with Cinnamamides: Access to 2-Phosphinoyl-3H-pyrrolo[1,2-a]indoles

(2017) Jian Xu et al.   ORGANIC LETTERS

Direct Phosphonation of Quinolinones and Coumarins Driven by the Photochemical Activity of Substrates and Products

(2017) Inwon Kim et al.   ORGANIC LETTERS

Synthesis of Tribenzo[b,e,g]phosphindole Oxides via Radical Bicyclization Cascades of o-Arylalkynylanilines

(2017) Jie Li et al.   ORGANIC LETTERS

Silver-Mediated Radical C(sp3)–H Biphosphinylation and Nitration of β-Alkynyl Ketones for Accessing Functional Isochromenes

(2017) Jun Sun et al.   ORGANIC LETTERS

Phosphinoyl Radical-Initiated α,β-Aminophosphinoylation of Alkenes

(2017) Jian-An Li et al.   ORGANIC LETTERS

Copper-catalyzed direct hydroxyphosphorylation of electron-deficient alkenes with H-phosphine oxides and dioxygen

(2017) Dong Yi et al.   TETRAHEDRON LETTERS

Mn III -catalyzed phosphorylation of vinyl azides: The synthesis of β-keto phosphine oxides

(2017) Pai Tang et al.   TETRAHEDRON LETTERS

Solvent-Controlled Copper-Catalyzed Radical Decarboxylative Coupling for Alkenyl C(sp2 )−P Bond Formation

(2017) Lin Tang et al.   Asian Journal of Organic Chemistry

Merging photoredox catalysis with transition metal catalysis: site-selective C4 or C5-H phosphonation of 8-aminoquinoline amides

(2017) Huijie Qiao et al.   Organic Chemistry Frontiers

Silver-Catalyzed Direct C$_{sp{^{2$H Phosphorylation of Indoles Leading to Phosphoindoles

(2016) Wang-Bin Sun et al.   ADVANCED SYNTHESIS & CATALYSIS

Copper-Catalyzed Cycloaddition between Secondary Phosphine Oxides and Alkynes: Synthesis of Benzophosphole Oxides

(2016) Pengbo Zhang et al.   ADVANCED SYNTHESIS & CATALYSIS

Dioxygen-induced oxidative activation of a P–H bond: radical oxyphosphorylation of alkenes and alkynes toward β-oxy phosphonates

(2016) Pan Peng et al.   CHEMICAL COMMUNICATIONS

Direct phosphonation of quinoxalin-2(1H)-ones under transition-metal-free conditions

(2016) Ming Gao et al.   CHEMICAL COMMUNICATIONS

K2S2O8-mediated metal-free direct P–H/C–H functionalization: a convenient route to benzo[b]phosphole oxides from unactivated alkynes

(2016) Dumei Ma et al.   GREEN CHEMISTRY

Silver-Catalyzed Cascade Radical Cyclization: A Direct Approach to 3,4-Disubstituted Dihydroquinolin-2(1H)-ones through Activation of the P–H Bond and Functionalization of the C(sp2)–H Bond

(2016) Honglin Zhang et al.   JOURNAL OF ORGANIC CHEMISTRY

Substituent-Controlled Chemoselective Cleavage of C═C or Csp2–C(CO) Bond in α,β-Unsaturated Carbonyl Compounds with H-Phosphonates Leading to β-Ketophosphonates

(2016) Yao Zhou et al.   JOURNAL OF ORGANIC CHEMISTRY

Autoxidative C(sp2)–P Formation: Direct Phosphorylation of Heteroarenes under Oxygen, Metal-Free, and Solvent-Free Conditions

(2016) Kai Luo et al.   JOURNAL OF ORGANIC CHEMISTRY

Manganese(III) Acetate-Promoted Cross-Coupling Reaction of Benzothiazole/Thiazole Derivatives with Organophosphorus Compounds under Ball-Milling Conditions

(2016) Liang Li et al.   JOURNAL OF ORGANIC CHEMISTRY

Metal-Free, Visible Light-Photocatalyzed Synthesis of Benzo[b]phosphole Oxides: Synthetic and Mechanistic Investigations

(2016) Valentin Quint et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Cascade Phosphinoylation/Cyclization/Isomerization Process for the Synthesis of 2-Phosphinoyl-9H-pyrrolo[1,2-a]indoles

(2016) Su Chen et al.   ORGANIC LETTERS

Metal-Free Synthesis of 6-Phosphorylated Phenanthridines: Synthetic and Mechanistic Insights

(2016) Ludovik Noël-Duchesneau et al.   ORGANIC LETTERS

A Cascade Phosphinoylation/Cyclization/Desulfonylation Process for the Synthesis of 3-Phosphinoylindoles

(2016) Yuzhen Gao et al.   ORGANIC LETTERS

Oxidative C(sp2)–H Phosphonation of Aldehyde Hydrazones

(2016) Pan Xu et al.   ORGANIC LETTERS

Metal-Free Visible-Light-Mediated Oxidative Cross-Coupling of Thiols with P(O)H Compounds Using Air as the Oxidant

(2016) Jian-Guo Sun et al.   ORGANIC LETTERS

Cross-Coupling Hydrogen Evolution by Visible Light Photocatalysis Toward C(sp2)–P Formation: Metal-Free C–H Functionalization of Thiazole Derivatives with Diarylphosphine Oxides

(2016) Kai Luo et al.   ORGANIC LETTERS

Visible-Light-Induced Cascade Reaction of Isocyanides and N-Arylacrylamides with Diphenylphosphine Oxide via Radical C–P and C–C Bond Formation

(2016) Chun-Xiao Li et al.   ORGANIC LETTERS

Electrochemical pathway to CH/PH functionalization of diphenylphosphine oxide

(2016) V.V. Khrizanforova et al.   PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS

Copper-catalyzed direct oxyphosphorylation of alkynes with H-phosphine oxides and dioxygen: A convenient approach toβ-ketophosphine oxides

(2016) Wen-Wu Zhong et al.   SYNTHETIC COMMUNICATIONS

Solvent-controlled direct radical oxyphosphorylation of styrenes mediated by Manganese(III)

(2016) Guo-Yu Zhang et al.   TETRAHEDRON

Catalyst-free direct difunctionalization of alkenes with H-phosphine oxides and dioxygen: a facile and green approach to β-hydroxyphosphine oxides

(2016) Meng-Shun Li et al.   TETRAHEDRON LETTERS

Copper-catalyzed cycloaddition between hydrogen phosphonates and activated alkenes: synthesis of phosphonoisoquinolinediones

(2016) Ju Wu et al.   RSC Advances

Silver-catalyzed synthesis of 2-arylvinylphosphonates by cross-coupling of β-nitrostyrenes with H-phosphites

(2016) Jin-Wei Yuan et al.   RSC Advances

Visible light mediated aerobic radical C–H phosphorization toward arylphosphonates

(2016) Pan Peng et al.   Organic Chemistry Frontiers

Metal-free oxidative hydrophosphinylation of 1,7-enynes

(2016) Yi-Long Zhu et al.   Organic Chemistry Frontiers

Copper-catalyzed radical cascade cyclization for the synthesis of phosphorated indolines

(2015) Hong-Yu Zhang et al.   CHEMICAL COMMUNICATIONS

Silver-mediated direct phosphorylation of benzothiazoles and thiazoles with diarylphosphine oxides

(2015) Hui-Jun Zhang et al.   CHEMICAL COMMUNICATIONS

Mn(OAc)3-mediated phosphonation–lactonization of alkenoic acids: synthesis of phosphono-γ-butyrolactones

(2015) Yuzhen Gao et al.   CHEMICAL COMMUNICATIONS

Copper-catalyzed tandem phosphination–decarboxylation–oxidation of alkynyl acids with H-phosphine oxides: a facile synthesis of β-ketophosphine oxides

(2015) Pengbo Zhang et al.   CHEMICAL COMMUNICATIONS

Stereoselective synthesis of vinylphosphonates and phosphine oxides via silver-catalyzed phosphorylation of styrenes

(2015) Qingwen Gui et al.   CHEMICAL COMMUNICATIONS

Cu/Fe-Cocatalyzed Formation of β-Ketophosphonates by a Domino Knoevenagel-Decarboxylation-Oxyphosphorylation Sequence from Aromatic Aldehydes and H-Phosphonates

(2015) Mingxin Zhou et al.   CHEMISTRY-A EUROPEAN JOURNAL

Copper-Catalyzed Phosphonation–Annulation Approaches to the Synthesis of β-Phosphonotetrahydrofurans Involving C–P and C–O Bonds Formation

(2015) Yuzhen Gao et al.   JOURNAL OF ORGANIC CHEMISTRY

Copper-catalyzed cascade addition/cyclization: highly efficient access to phosphonylated quinoline-2,4(1H,3H)-diones

(2015) Ya-Min Li et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Ag-mediated cascade decarboxylative coupling and annulation: a convenient route to 2-phosphinobenzo[b]phosphole oxides

(2015) Gaobo Hu et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Silver-Catalyzed Oxidative Cyclization of Propargylamide-Substituted Indoles: Synthesis of Phosphorated Indoloazepinones Derivatives

(2015) Hui-Liang Hua et al.   ORGANIC LETTERS

β-Ketophosphonate Formation via Aerobic Oxyphosphorylation of Alkynes or Alkynyl Carboxylic Acids with H-Phosphonates

(2015) Mingxin Zhou et al.   ORGANIC LETTERS

Metal-free direct difunctionalization of alkenes with I2O5 and P(O)–H compounds leading to β-iodophosphates

(2015) Chunli Liu et al.   Organic Chemistry Frontiers

Arylphosphonylation and Arylazidation of Activated Alkenes

(2014) Wangqing Kong et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Radical phosphinylation of α,α-diaryl allylic alcohols with concomitant 1,2-aryl migration

(2014) Xue-Qiang Chu et al.   CHEMICAL COMMUNICATIONS

Silver-catalyzed carbon–phosphorus functionalization of N-(p-methoxyaryl)propiolamides coupled with dearomatization: access to phosphorylated aza-decenones

(2014) Li-Jing Wang et al.   CHEMICAL COMMUNICATIONS

Manganese-Mediated Intermolecular Arylation ofH-Phosphinates and Related Compounds

(2014) Olivier Berger et al.   CHEMISTRY-A EUROPEAN JOURNAL

Direct Radical Acetoxyphosphorylation of Styrenes Mediated by Manganese(III)

(2014) Shao-Fang Zhou et al.   JOURNAL OF ORGANIC CHEMISTRY

Peroxides as “Switches” of Dialkyl H-Phosphonate: Two Mild and Metal-Free Methods for Preparation of 2-Acylbenzothiazoles and Dialkyl Benzothiazol-2-ylphosphonates

(2014) Xiao-Lan Chen et al.   JOURNAL OF ORGANIC CHEMISTRY

Manganese(III)-Mediated Selective Diphenylphosphinoyl Radical Reaction of 1,4-Diaryl-1-butynes for the Synthesis of 2-Phosphinoylated 3,4-Dihydronaphathalenes

(2014) Da-Peng Li et al.   JOURNAL OF ORGANIC CHEMISTRY

Nickel-Catalyzed Decarboxylative C–P Cross-Coupling of Alkenyl Acids with P(O)H Compounds

(2014) Yile Wu et al.   JOURNAL OF ORGANIC CHEMISTRY

Synthesis of π-Extended Dibenzophospholes by Intramolecular Radical Cyclization and Their Properties

(2014) Shunsuke Furukawa et al.   ORGANIC LETTERS

Silver-Catalyzed Synthesis of 3-Phosphorated Coumarins via Radical Cyclization of Alkynoates and Dialkyl H-Phosphonates

(2014) Xia Mi et al.   ORGANIC LETTERS

Advances and New Variations of the Hirao Reaction

(2014) Erzsébet Jablonkai et al.   ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL

Copper-Catalyzed Oxidative Cross-Coupling of H-Phosphine Oxides with Alkenes in the Synthesis of Alkenylphosphine Oxides

(2014) Shang-Dong Yang et al.   SYNLETT

Copper(I) Iodide Mediated Synthesis of Carbohydrate-Based Terminal Allenes by ATA Reaction

(2014) Shengming Ma et al.   SYNTHESIS-STUTTGART

Silver-catalyzed 2-isocyanobiaryls insertion/cyclization with phosphine oxides: synthesis of 6-phosphorylated phenanthridines

(2014) Jia-Jia Cao et al.   TETRAHEDRON

Mn(OAc)3-mediated synthesis of β-hydroxyphosphonates from P(O)–H compounds and alkenes

(2014) Yuzhen Gao et al.   RSC Advances

P-C Bond Formation by Coupling Reactions Utilizing >P(O)H Species as the Reagents

(2013) Erzsebet Jablonkai et al.   CURRENT ORGANIC SYNTHESIS

Silver-Mediated Oxidative C–H/P–H Functionalization: An Efficient Route for the Synthesis of Benzo[b]phosphole Oxides

(2013) Yun-Rong Chen et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

6-Phosphorylated Phenanthridines from 2-Isocyanobiphenyls via Radical C–P and C–C Bond Formation

(2013) Bo Zhang et al.   ORGANIC LETTERS

Ruthenium-catalyzed hydrophosphinylative cyclization of 1,6-diynes. Stereoselective synthesis of exocyclic 1,3-dienylphosphine oxides

(2012) Yoshihiko Yamamoto et al.   CHEMICAL COMMUNICATIONS

Manganese(iii)-mediated phosphinoyl radical reactions for stereoselective synthesis of phosphinoylated tetrahydronaphthalenes

(2011) Xiang-Qiang Pan et al.   CHEMICAL COMMUNICATIONS

Copper-Catalyzed C-P Coupling through Decarboxylation

(2011) Jie Hu et al.   CHEMISTRY-A EUROPEAN JOURNAL