Unusual Application for Phosphonium Salts and Phosphoranes: Synthesis of Chalcogenides

Moura, Igor M. R.; Tranquilino, Arisson; Sátiro, Barbara G.; Silva, Ricardo Oliveira; Oliveira‐Silva, Diogo; Oliveira, Roberta A.; Menezes, Paulo H.

doi:10.1021/acs.joc.1c00114

Cited by 5 publications

(5 citation statements)

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“…The removal of the sulfonyl-phosphonium species 127 followed by protonation gives the target compounds 123. [79] Very recently, Chen reported a practical difluoromethylation of variously functionalized selenosulfones with [Ph 3 PCF 2 H]Br (compound 129, Scheme 31) under visible-light activation. Also in this case the applicability is pretty general with a wide array of substrates converted into their difluoromethylseleno analogues in good isolated yields.…”

Section: Reactions With Phosphorus Containing Compoundsmentioning

confidence: 99%

“…Conversely, in the case of the presence of a benzyl group in R, the α‐hydrogen are not acidic enough thus leading to the nucleophilic attack of the sulfonyl anion to the electrophilic phosphonium ion. The removal of the sulfonyl‐phosphonium species 127 followed by protonation gives the target compounds 123 [79] …”

Section: Reactions With Phosphorus Containing Compoundsmentioning

confidence: 99%

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Selenosulfones, a Meetup of Chalcogens: A Journey Into Their Recent Chemistry

Bagnoli,

Rosati,

Marini

et al. 2024

Eur J Org Chem

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A mini review focused on the chemistry of selenosulfones reported since 2019 is here presented. Initially, methods aimed to the preparation of such moiety are discussed. Successively 1,2‐, 1,3‐, 1,4‐ and 1,7‐addition reactions to C‐C single and multiple bonds are illustrated. The third chapter deals with C‐H functionalizations while the fourth one shows the reactions with aryl diazonium salts or its precursors. The radical coupling with redox active reagents, is the subject of section five. Selenosulfones challenged in nucleophilic substitutions and in reactions with phosphorus‐containing compounds are shown in chapter six and seven followed by the conclusions and perspectives section.

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Section: Reactions With Phosphorus Containing Compoundsmentioning

confidence: 99%

Section: Reactions With Phosphorus Containing Compoundsmentioning

confidence: 99%

Selenosulfones, a Meetup of Chalcogens: A Journey Into Their Recent Chemistry

Bagnoli,

Rosati,

Marini

et al. 2024

Eur J Org Chem

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“…UV spectra (A) and rhodamine B release profile (B) within time in the absence of nanoparticles (1) and encapsulated in liposomes (2-5) are shown in Figure 3. Rhodamine B (50%) was released from liposomes much slower (4 h) than in the case of aqueous solution (within 20 min).…”

Section: Liposomal Systems Based On Amphiphilic Triflates Of Acyloxypropylphosphonium and L-α-phosphatidylcholinementioning

confidence: 99%

“…Phosphonium salts (QPSs) are organoelement compounds of importance in chemistry, pharmacology, biochemistry, etc. [1][2][3][4]. QPSs are used as organocatalysts in the reactions of C-C bond formation, annulation, etc., as a Lewis acid in organic synthesis [5].…”

Section: Introductionmentioning

confidence: 99%

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Rational Design 2-Hydroxypropylphosphonium Salts as Cancer Cell Mitochondria-Targeted Vectors: Synthesis, Structure, and Biological Properties

et al. 2021

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It has been shown for a wide range of epoxy compounds that their interaction with triphenylphosphonium triflate occurs with a high chemoselectivity and leads to the formation of (2-hydroxypropyl)triphenylphosphonium triflates 3 substituted in the 3-position with an alkoxy, alkylcarboxyl group, or halogen, which were isolated in a high yield. Using the methodology for the disclosure of epichlorohydrin with alcohols in the presence of boron trifluoride etherate, followed by the substitution of iodine for chlorine and treatment with triphenylphosphine, 2-hydroxypropyltriphenylphosphonium iodides 4 were also obtained. The molecular and supramolecular structure of the obtained phosphonium salts was established, and their high antitumor activity was revealed in relation to duodenal adenocarcinoma. The formation of liposomal systems based on phosphonium salt 3 and L-α-phosphatidylcholine (PC) was employed for improving the bioavailability and reducing the toxicity. They were produced by the thin film rehydration method and exhibited cytotoxic properties. This rational design of phosphonium salts 3 and 4 has promising potential of new vectors for targeted delivery into mitochondria of tumor cells.

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