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

Sato, Yuki; Kawaguchi, Shin‐ichi; Nomoto, Akihiro

doi:10.1055/s-0036-1588867

Cited by 13 publications

(5 citation statements)

References 18 publications

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“…An elegant example of the synthesis of organoselenyl phosphinates 185 has been reported through a photoinduced coupling reaction of diphenyl(2,4,6‐trimethylbenzoyl) phosphine oxide (TMDPO) with diorganyl diselenides (Scheme 177). The authors′ strategy was based on the photoirradiation of TMDPO to form a pentavalent phosphorus radical Ph 2 P(O)•, which attacks diorganyl diselenide to give the corresponding organoselenyl phosphinate [254] . After this work, the same authors found that the reaction conditions could be successfully employed to diphosphine disulfide with diorganyl diselenides to give the corresponding diphenylphosphino selenides [255] …”

Section: Diorganyl Diselenides Promoting Organoselenylation Of Organo...mentioning

confidence: 99%

Recent Progress in Synthetic and Biological Application of Diorganyl Diselenides

do Carmo Pinheiro,

Souza Marques,

Ten Kathen Jung

et al. 2024

The Chemical Record

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Diorganyl diselenides have emerged as privileged structures because they are easy to prepare, have distinct reactivity, and have broad biological activity. They have also been used in the synthesis of natural products as an electrophile in the organoselenylation of aromatic systems and peptides, reductions of alkenes, and nucleophilic substitution. This review summarizes the advancements in methods for the transformations promoted by diorganyl diselenides in the main functions of organic chemistry. Parallel, it will also describe the main findings on pharmacology and toxicology of diorganyl diselenides, emphasizing anti‐inflammatory, hypoglycemic, chemotherapeutic, and antimicrobial activities. Therefore, an examination detailing the reactivity and biological characteristics of diorganyl diselenides provides valuable insights for academic researchers and industrial professionals.

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Section: Diorganyl Diselenides Promoting Organoselenylation Of Organo...mentioning

confidence: 99%

Recent Progress in Synthetic and Biological Application of Diorganyl Diselenides

do Carmo Pinheiro,

Souza Marques,

Ten Kathen Jung

et al. 2024

The Chemical Record

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“…Under photoirradiation, the homolytic cleavage of the P V (O)–C(O) bond in TMDPO occurred to form Ph 2 P(O) • and MesC(O) • . Then, the formed radicals reacted with dichalcogenides via S H 2 reaction or radical coupling pathways, and the corresponding thio- or selenophosphinates and thio- or selenoesters, respectively, were obtained in excellent yields ( Scheme 13 ) [ 65 ].…”

Section: Phosphorus-centered Interelement Compounds In Radical Reactionsmentioning

confidence: 99%

Metal-Free One-Pot Multi-Functionalization of Unsaturated Compounds with Interelement Compounds by Radical Process

Yamamoto

2023

Molecules

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In recent years, the importance of “environmentally friendly manufacturing” has been increasing toward the establishment of a resource-recycling society. In organic synthesis, as well, it is becoming increasingly important to develop new synthetic strategies with resource conservation and the recycling of elemental resources in mind, rather than just only synthesis. Many studies on the construction of frameworks of functional molecules using ionic reactions and transition-metal-catalyzed reactions have been reported, but most of them have focused on the formation of carbon–carbon bonds. However, it is essential to introduce appropriate functional groups at appropriate positions in molecules in order for the molecules to express their functions, and furthermore, the highly selective preparation of multiple functional groups is considered important for the creation of new functional molecules. In this review, we focus on radical reactions with high functional group selectivity and overview the recent progress in practical methods for the simultaneous introduction of multiple functional groups and propose future synthetic strategies that emphasize the recycling of elemental resources and environmental friendliness.

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“…In addition, Ogawa's group [35] reported a metal‐free and catalyst‐free approach for the efficient construction of phosphinothioates 15 via photo‐induced coupling reaction between diphenyl (2,4,6‐trimethylbenzoyl) phosphine oxide 54 (TMDPO), and disulfides 14 under mild conditions (Scheme 21). Some representative thiophosphates were successfully constructed in good to excellent yields.…”

Section: Photo‐induced Radical Transformation To Construct Sulfur‐con...mentioning

confidence: 99%

Recent Advances in the Direct Synthesis of Sulfur‐Containing Organophosphorus Compounds via Radical Processes

et al. 2023

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Phosphonothioates, phosphinothioates and phosphorothioates are regarded as an important class of sulfur‐containing organophosphorus compounds. Because of the unique P(O)S−R group, these compounds have important biological activities and thus have been widely used in the fields of pharmaceuticals and pesticides. In recent years, the development of sulfur‐containing organophosphorus compounds by radical processes has attracted considerable attention in organophosphorus chemistry. Along these lines, in this review, the recent advances in the synthesis of sulfur‐containing organophosphorus compounds were systematically summarized. According to the different ways of generating radicals during the formation process of phosphonothioates, phosphinothioates and phosphorothioates, these transformations can be divided into four categories: (1) Oxidant or metal‐free promoted radical transformation to fabricate sulfur‐containing organophosphorus compounds; (2) Copper‐catalyzed radical transformation to produce sulfur‐containing organophosphorus compounds; (3) Photo‐induced radical transformation to prepare sulfur‐containing organophosphorus compounds; (4) Electro‐induced radical transformation to derive sulfur‐containing organophosphorus compounds.

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

Cited by 13 publications

References 18 publications

Recent Progress in Synthetic and Biological Application of Diorganyl Diselenides

Recent Progress in Synthetic and Biological Application of Diorganyl Diselenides

Metal-Free One-Pot Multi-Functionalization of Unsaturated Compounds with Interelement Compounds by Radical Process

Recent Advances in the Direct Synthesis of Sulfur‐Containing Organophosphorus Compounds via Radical Processes

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