A simple and new method for the synthesis of thiophosphates

Kaboudin, Babak

doi:10.1016/s0040-4039(02)02136-6

Cited by 64 publications

(12 citation statements)

References 28 publications

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“…12 We recently reported a novel synthetic preparation of phosphorothioates by reaction of diethyl phosphite with alkyl halides in the presence of a mixture of ammonium acetate/sulfur/alumina under solvent-free conditions using microwave irradiation. 13 This methodology prompted us to try the use of other metal oxides in place of the acidic alumina in the above reaction for the preparation of phosphorothioates. We found that replacing of alumina with calcium oxide is a convenient solid media that does not need microwave irradiation in first step of above reaction.…”

Section: A Convenient Methods For the Synthesis Of Phosphorothioates Amentioning

confidence: 99%

A Convenient Method for the Synthesis of Phosphorothioates and Their Anticholinesterase Activities

Kaboudin

Emadi

Norouzi

2004

Phosphorus, Sulfur, and Silicon and the Related Elements

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Section: A Convenient Methods For the Synthesis Of Phosphorothioates Amentioning

confidence: 99%

A Convenient Method for the Synthesis of Phosphorothioates and Their Anticholinesterase Activities

Kaboudin

Emadi

Norouzi

2004

Phosphorus, Sulfur, and Silicon and the Related Elements

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“…1 2.1 Synthesis of Phosphoric Acids and Their Derivatives. 2 Trimethylsilyl phosphorohalidates (6) and (7) have been synthesized from phosphoryl dihalogenofluoride (8) and hexamethyldisiloxane (9). 2 Trimethylsilyl phosphorohalidates (6) and (7) have been synthesized from phosphoryl dihalogenofluoride (8) and hexamethyldisiloxane (9).…”

Section: Phosphoric Acids and Their Derivativesmentioning

confidence: 99%

“…The mechanism of activation by 2,4-DNP and cyclization was also described ( Figure 3). 7 Two diastereoisomers of 1,3,2dithiadiphosphetane 2-sulfide (19) have been isolated for the first time via the reaction of thioketones (20) with Lawesson's reagent ( Figure 5). 7 Two diastereoisomers of 1,3,2dithiadiphosphetane 2-sulfide (19) have been isolated for the first time via the reaction of thioketones (20) with Lawesson's reagent ( Figure 5).…”

Section: Phosphoric Acids and Their Derivativesmentioning

confidence: 99%

Organophosphorus Chemistry

Hall

Bricklebank

Grampel³

et al. 2006

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Organophosphorus compounds are ubiquitous in nature, and due to their innate chemical properties, serve a fundamental role in a number of important fields. Among the more prominent features that elevate their status as a unique and versatile class of compounds, include variable oxidation states, multivalency, asymmetry and metal-binding properties. Their presence in bioactive natural products, endogenous biomolecules, small molecule therapeutic agents and pro-drugs substantiates their role in modern synthetic chemistry and chemical biology. Moreover, their central use as ligands and effectors in asymmetric catalysis, as well as key functional groups for the development of new synthetic methods, has taken the field to new heights. This Thematic Series highlights and details some of the novel methods that are advancing the field of organophosphorus chemistry.The Thematic Series covers topics that range from new synthetic methods and phosphorus-based ligands in asymmetric catalysis to bisphosphonates as promising enzyme inhibitors. More specifically, the Thematic Series spans new methods in C-P bond formation, chiral phosphines in nucleophilic organocatalysis, chiral N-phosphinyl auxiliaries, cyclic phosphonamide reagents in the total synthesis of natural products, phosphinate-containing heterocycles, new routes to phosphinoyl-indoles and phosphinoyl-isocoumarins and new chemistries of H-phosphonates. The Thematic Series also details work on new metathesis-based reactions of vinyl phosphonates and phosphate tethers, novel phosphorus-based ligands in asymmetric catalysis, novel rasta resin-triphenylphosphine oxides and their use as recyclable heterogeneous reagents, the Atherton-Todd reaction, cyclic phosphonium ionic liquids with distinct properties, photo-removable phosphate protecting groups, new methods of C-H functionalization using phosphoryl-related directing groups, the exciting chemistry of substituted phosphanylidenecarbenes and phosphoryl azides, and bisphosphonate ethers as promising inhibitors of geranylgeranyl diphosphate synthase (GGDPS).The articles and reviews capture the emerging potential of organophosphorus compounds and exciting opportunities in the field, and hopefully, will inspire and motivate investigators in the field to investigate new chemistry in this area. Taken collectively, organophosphorus chemistry embodies a broad, vibrant and continual growing scientific area with this Thematic Series highlighting recent advances in the field. We are grateful and indebted to the authors for their hard work and exciting contri-

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“…If the desired PÀ S bond is already in place in the starting material, alkylation at sulfur represents an attractive alternative to these other methods. [21] Recent work by Gooßen and co-workers has demonstrated that the alkylation of shelf stable tetraalkylammonium phosphorothioate salts, generated from the corresponding silyl phosphite and elemental sulfur, afforded high yields of the corresponding phosphorothioates. [22] It is unclear, however, whether this approach could be adapted to other classes of Salkyl organophosphorus compounds.…”

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A Robust Methodology for the Synthesis of Phosphorothioates, Phosphinothioates and Phosphonothioates

2020

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A robust methodology for the synthesis of phosphorothioates, phosphinothioates and phosphonothioates, including those bearing low molecular weight S-alkyl side-chains, is presented. Application of the "caesium effect" in conjunction with the disulfide 3,3'-dithiobis(propionitrile), which acts as a shelf-stable sulfur source, avoids recourse to malodorous alkanethiols and toxic PÀ Cl precursors. A diverse range of sulfur-containing organophosphorus targets, including phosphorus-based heterocycles, may be prepared in consistently high yields. This chemistry also provides ready access to the corresponding DBU salts which are potential substrates for Pd-catalysed coupling reactions. Scheme 3. Investigation of substrate scope of telescoped process. a) R 3 I (1.0 mmol), r.t., 3 h; b) R 3 Br (1.00 mmol), reflux, 3 h.

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A simple and new method for the synthesis of thiophosphates

Cited by 64 publications

References 28 publications

A Convenient Method for the Synthesis of Phosphorothioates and Their Anticholinesterase Activities

A Convenient Method for the Synthesis of Phosphorothioates and Their Anticholinesterase Activities

Organophosphorus Chemistry

A Robust Methodology for the Synthesis of Phosphorothioates, Phosphinothioates and Phosphonothioates

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