Modern Synthetic Approaches to Phosphorus‐Sulfur Bond Formation in Organophosphorus Compounds

A robust methodology for the synthesis of phosphorothioates, phosphinothioates and phosphonothioates.

(2020) David Jones et al.   ADVANCED SYNTHESIS & CATALYSIS

Copper-Catalyzed Remote C(sp3)–H Phosphorothiolation of Sulfonamides and Carboxamides in a Multicomponent Reaction

(2020) Shanshan Shi et al.   ORGANIC LETTERS

Lewis Acid Promoted Aerobic Oxidative Coupling of Thiols with Phosphonates by Simple Nickel(II) Catalyst: Substrate Scope and Mechanistic Studies

(2019) Jing-Wen Xue et al.   JOURNAL OF ORGANIC CHEMISTRY

An improved synthesis of adefovir and related analogues

(2019) David J Jones et al.   Beilstein Journal of Organic Chemistry

Iodide‐Catalyzed Phosphorothiolation of Heteroarenes Using P(O)H Compounds and Elemental Sulfur

(2019) Shanshan Shi et al.   ADVANCED SYNTHESIS & CATALYSIS

Benign synthesis of thiophosphates, thiophosphinates and selenophosphates in neat condition using N-chalcogenoimides as the source of electrophilic sulfur/selenium

(2019) Manas Mondal et al.   TETRAHEDRON LETTERS

An Alternative Metal-Free Aerobic Oxidative Cross-Dehydrogenative Coupling of Sulfonyl Hydrazides with Secondary Phosphine Oxides

(2019) Teng Liu et al.   SYNTHESIS-STUTTGART

Reactions of Disulfides with Silyl Phosphites to Generate Thiophosphates Under Neat Conditions

(2018) Zhen Zhan et al.   ChemSusChem

Cu(II)/Proline-Catalyzed Reductive Coupling of Sulfuryl Chloride and P(O)–H for P–S–C Bond Formation

(2018) Xinghua Zhang et al.   JOURNAL OF ORGANIC CHEMISTRY

Fast and transition metal-free general method for the preparation of chalcogenophosphates

(2018) Junxing Wang et al.   JOURNAL OF ORGANOMETALLIC CHEMISTRY

Metal-free electrophilic phosphination of electron-rich arenes, arenols and aromatic thiols with diarylphosphine oxides

(2018) Tao Yuan et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Base-controlled Fe(Pc)-catalyzed aerobic oxidation of thiols for the synthesis of S–S and S–P(O) bonds

(2018) Hai Huang et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Phosphoric acid as a precursor to chemicals traditionally synthesized from white phosphorus

(2018) Michael B. Geeson et al.   SCIENCE

Visible light photoredox catalyzed thiophosphate synthesis using methylene blue as a promoter

(2018) Hao Zhang et al.   Organic Chemistry Frontiers

Practical Reagents and Methods for Nucleophilic and Electrophilic Phosphorothiolations

(2018) Szabolcs Kovács et al.   ADVANCED SYNTHESIS & CATALYSIS

Unlocking P(V): Reagents for chiral phosphorothioate synthesis

(2018) Kyle W. Knouse et al.   SCIENCE

Synthesis and application of phosphonothioates, phosphonodithioates, phosphorothioates, phosphinothioates and related compounds

(2018) David J. Jones et al.   TETRAHEDRON LETTERS

Indoles as therapeutics of interest in medicinal chemistry: Bird's eye view

(2017) Navriti Chadha et al.   EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY

Three-Component Coupling Reaction in Water: A One-Pot Protocol for the Construction of P-S-C(sp3 ) and P-Se-C(sp3 ) Bonds

(2017) Xinghua Zhang et al.   EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Metal- and oxidant-free S–P(O) bond construction via direct coupling of P(O)H with sulfinic acids

(2017) Youngtaek Moon et al.   GREEN CHEMISTRY

Dimethyl sulfoxide as a mild oxidant in S–P(O) bond construction: simple and metal-free approaches to phosphinothioates

(2017) Jian-Guo Sun et al.   GREEN CHEMISTRY

Synthesis and Characterization of 2-Phenylimidazo[1,2-a]pyridine: A Privileged Structure for Medicinal Chemistry

(2017) Brandi S. Santaniello et al.   JOURNAL OF CHEMICAL EDUCATION

Metal- and base-free reductive coupling reaction of P(O)–H with aryl/alkyl sulfonyl chlorides: a novel protocol for the construction of P–S–C bonds

(2017) Dungai Wang et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Recent progress toward organophosphorus compounds based on phosphorus-centered radical difunctionalizations

(2017) Yuzhen Gao et al.   PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS

Photoinduced Coupling Reaction of Diphenyl(2,4,6-trimethylbenzoyl)phosphine Oxide with Interelement Compounds: Application to the Synthesis of Thio- or Selenophosphinates

(2017) Shin-ichi Kawaguchi et al.   SYNTHESIS-STUTTGART

Synthesis of P(O)-S organophosphorus compounds by dehydrogenative coupling reaction of P(O)H compounds with aryl thiols in the presence of base and air

(2017) Wei He et al.   TETRAHEDRON

Synthesis of symmetrically and unsymmetrically substituted S,S -dialkyl phosphonodithioates

(2017) David J. Jones et al.   TETRAHEDRON LETTERS

CDI-promoted direct esterification of P(O)-OH compounds with phenols

(2017) Biquan Xiong et al.   TETRAHEDRON LETTERS

Magnetically recyclable Cu-BTC@Fe3O4 composite-catalyzed C(aryl)–S–P bond formation using aniline, P(O)H compounds and sulfur powder

(2017) Liang Wang et al.   Catalysis Science & Technology

K2CO3-promoted aerobic oxidative cross-coupling of trialkyl phosphites with thiophenols

(2017) Chunxiao Wen et al.   RSC Advances

Synthesis of thiophosphates through a three-component reaction by using sulfur dioxide as the sulfur source

(2017) Xinxing Gong et al.   Organic Chemistry Frontiers

Rhodium-catalyzed P–P bond exchange reaction of diphosphine disulfides

(2016) Mieko Arisawa et al.   CHEMICAL COMMUNICATIONS

Organic Photoredox Catalysis

(2016) Nathan A. Romero et al.   CHEMICAL REVIEWS

Recent advances in the chemistry of organic thiocyanates

(2016) Thomas Castanheiro et al.   CHEMICAL SOCIETY REVIEWS

Acid/Phosphide-Induced Radical Route to Alkyl and Alkenyl Sulfides and Phosphonothioates from Sodium Arylsulfinates in Water

(2016) Ya-mei Lin et al.   JOURNAL OF ORGANIC CHEMISTRY

Stereospecific Preparations of P-Stereogenic Phosphonothioates and Phosphonoselenoates

(2016) Wei-Min Wang et al.   JOURNAL OF ORGANIC CHEMISTRY

Synthesis of S-Aryl Phosphorothioates by Copper-Catalyzed Phosphorothiolation of Diaryliodonium and Arenediazonium Salts

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

Efficient Pd-Catalyzed Dehydrogenative Coupling of P(O)H with RSH: A Precise Construction of P(O)–S Bonds

(2016) Yueyue Zhu et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Phosphorothiolation of Aryl Boronic Acids Using P(O)H Compounds and Elemental Sulfur

(2016) Jian 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

DCDMH-promoted synthesis of thiophosphates by coupling of H-phosphonates with thiols

(2016) Xiaojing Bi et al.   TETRAHEDRON

Direct synthesis of thiophosphates by reaction of diphenylphosphine oxide with sulfonyl chlorides

(2016) Wei He et al.   TETRAHEDRON

Catalyst- and oxidant-free coupling of disulfides with H-phosphine oxide: construction of P–S bond leading to thiophosphinates

(2016) Minfang Xia et al.   TETRAHEDRON LETTERS

Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes

(2015) Darrin M. Flanigan et al.   CHEMICAL REVIEWS

TBPB-promoted metal-free synthesis of thiophosphinate/phosphonothioate by direct P–S bond coupling

(2015) Jichao Wang et al.   GREEN CHEMISTRY

P(═O)H to P–OH Tautomerism: A Theoretical and Experimental Study

(2015) Benjamin G. Janesko et al.   JOURNAL OF ORGANIC CHEMISTRY

Peroxide promoted metal-free thiolation of phosphites by thiophenols/disulfides

(2015) Jichao Wang et al.   TETRAHEDRON

Chloroform-based Atherton–Todd-type reactions of alcohols and thiols with secondary phosphine oxides generating phosphinothioates and phosphinates

(2015) Shan Li et al.   RSC Advances

Copper(I)-Induced Sulfenylation of H-Phosphonates, H-Phosphonites and Phosphine Oxides with Aryl/alkylsulfonylhydrazides as a Thiol Surrogate

(2014) Gullapalli Kumaraswamy et al.   ADVANCED SYNTHESIS & CATALYSIS

The Catalytic Asymmetric Abramov Reaction

(2014) Joyram Guin et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Environmentally benign synthesis and antimicrobial study of novel chalcogenophosphates

(2014) Shubhanjan Mitra et al.   BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

Copper-catalyzed reductive coupling of aryl sulfonyl chlorides with H-phosphonates leading to S-aryl phosphorothioates

(2014) Jie Bai et al.   CHEMICAL COMMUNICATIONS

Copper-promoted oxidative-fluorination of arylphosphine under mild conditions

(2014) Na Liu et al.   CHEMICAL COMMUNICATIONS

Synthesis of Nucleoside Phosphate and Phosphonate Prodrugs

(2014) Ugo Pradere et al.   CHEMICAL REVIEWS

Tuning Thiophene with Phosphorus: Synthesis and Electronic Properties of Benzobisthiaphospholes

(2014) Yunyan Qiu et al.   CHEMISTRY-A EUROPEAN JOURNAL

Enantioselective Interaction of Acid α-Naphthyl Acetate Esterase with Chiral Organophosphorus Insecticides

(2014) Anping Zhang et al.   JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY

An overview of N-heterocyclic carbenes

(2014) Matthew N. Hopkinson et al.   NATURE

New benzotriazole-based reagents for the phosphonylation of various N-, O-, and S-nucleophiles

(2014) Deepak S. Panmand et al.   TETRAHEDRON LETTERS

Thiophosphate and thiophosphonate analogues of glucose-1-phosphate: synthesis and enzymatic activity with a thymidylyltransferase

(2013) Matthew W. Loranger et al.   CARBOHYDRATE RESEARCH

A simple and convenient method for the synthesis of S-aryl phosphorothioates catalyzed by cesium hydroxide

(2013) Yue-Jun Ouyang et al.   CHINESE CHEMICAL LETTERS

Ester prodrugs of acyclic nucleoside thiophosphonates compared to phosphonates: Synthesis, antiviral activity and decomposition study

(2013) Loïc Roux et al.   EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY

N-Chlorosuccinimide-promoted synthesis of thiophosphates from thiols and phosphonates under mild conditions

(2013) Yi-Chen Liu et al.   GREEN CHEMISTRY

5′-Phosphate and 5′-Phosphonate Ester Derivatives of (N)-Methanocarba Adenosine with in Vivo Cardioprotective Activity

(2013) T. Santhosh Kumar et al.   JOURNAL OF MEDICINAL CHEMISTRY

A simple route to dithiophosphinic esters and diesters from secondary phosphine sulfides and thiols or dithiols

(2013) P.A. Volkov et al.   Journal of Sulfur Chemistry

Stereoselective Synthesis of P-Modified α-Glycosyl Phosphates by the Oxazaphospholidine Approach

(2013) Mihoko Noro et al.   ORGANIC LETTERS

Copper(I) Iodide Catalyzed Synthesis of Thiophosphates by Coupling of H-Phosphonates with Benzenethiols

(2013) Babak Kaboudin et al.   SYNTHESIS-STUTTGART

Systematic study for the stereochemistry of the Atherton–Todd reaction

(2013) Biquan Xiong et al.   TETRAHEDRON

Design, synthesis and biological evaluation of organophosphorous-homodimers as dual binding site acetylcholinesterase inhibitors

(2012) Ruliang Xie et al.   BIOORGANIC & MEDICINAL CHEMISTRY

Synthesis, Properties, and Applications of Oligonucleotides Containing an RNA Dinucleotide Phosphorothiolate Linkage

(2011) Nan-Sheng Li et al.   ACCOUNTS OF CHEMICAL RESEARCH

Eosin Y Catalyzed Visible Light Oxidative C–C and C–P bond Formation

(2011) Durga Prasad Hari et al.   ORGANIC LETTERS

Stereospecific Halogenation of P(O)-H Bonds with Copper(II) Chloride Affording Optically Active Z1Z2P(O)Cl

(2010) Yongbo Zhou et al.   JOURNAL OF ORGANIC CHEMISTRY

Stereospecific Coupling ofH-Phosphinates and Secondary Phosphine Oxides with Amines and Alcohols: A General Method for the Preparation of Optically Active Organophosphorus Acid Derivatives†

(2010) Gang Wang et al.   JOURNAL OF ORGANIC CHEMISTRY

Synthesis of novel phosphorothioates and phosphorodithioates and their differential inhibition of cholinesterases

(2009) Babak Kaboudin et al.   BIOORGANIC CHEMISTRY

Thiophosphorylation of free amino acids and enzyme protein by thiophosphoramidate ions

(2009) Tomasz Ruman et al.   BIOORGANIC CHEMISTRY

Singlet Oxygen Generation from [Bis(trifluoroacetoxy)iodo]benzene and Hydrogen Peroxide

(2009) Mustafa Catir et al.   JOURNAL OF ORGANIC CHEMISTRY

Highly Enantioselective Synthesis of Heteroaromatic Alcohols Catalyzed by Chiral Diaminodiphosphine-Ruthenium(II) Complexes

(2009) Jing-Xing Gao et al.   SYNTHESIS-STUTTGART

Organophosphorus Derivatives Containing Isatin-3-hydrazones as Chemotherapeutants against Fungal Pathogens of Sugarcane

(2008) V. K. Pandey et al.   JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY

Synthesis of S-glycosyl thiophosphates, thiophosphonates and thiophosphinates by the Michaelis–Arbuzov rearrangement of anomeric thiocyanates

(2007) Marta Piekutowska et al.   CARBOHYDRATE RESEARCH