A New Method of Introducing SCH<sub>3</sub>and SCD<sub>3</sub>Groups to Phosphorothioates

Liu, Tianzhen; Cui, Xiaoxue; Zhang, Yu; Li, Chunbao

doi:10.1080/10426507.2011.634467

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Dmso/activating Agents Promoted Methylthiolation1

P-s Bond Formation From P-nucleophile and S-electrophile1

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2022

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Cited by 7 publications

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“…In 2011, Li and coworkers 45 reported a protocol for the synthesis of phosphorothioates 2 from phosphites 1 using a cyanuric chloride (TCT)–DMSO/DMSO- d 6 system. The reaction was postulated to start from the TCT-promoted activation of DMSO, which led to the formation of sulfonium salt 3 .…”

Section: Dmso/activating Agents Promoted Methylthiolationmentioning

confidence: 99%

Application of DMSO as a methylthiolating reagent in organic synthesis

Wang

et al. 2022

Org. Biomol. Chem.

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Section: Dmso/activating Agents Promoted Methylthiolationmentioning

confidence: 99%

Application of DMSO as a methylthiolating reagent in organic synthesis

Wang

et al. 2022

Org. Biomol. Chem.

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“…Li et al have developed a synthesis for S-methyl and S-butyl phosphorothioates starting from various phosphites and dimethyl or dibutyl sulfoxide, activated by 2,4,6-trichloro[1,3,5]-triazine (cyanuric chloride, TCT). [13] The procedure was also applied to the introduction of SCD3 group into bioactive phosphorothioates. The high purity of the obtained deuterated derivatives allows their use in mechanistic biological studies (Scheme 6).…”

Section: P-s Bond Formation From P-nucleophile and S-electrophilementioning

confidence: 99%

Progress in the Chemistry of Phosphorothioates

Gulea¹

2018

Advances in Organic Synthesis

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The present review focuses on the synthesis and applications of phosphorothioates (phosphorothioic esters) with the general structure R2P(O)SR', which are molecules belonging to the large family of organophosphorus compounds. They found important applications as biological active molecules, as well as synthetic intermediates to access valuable phosphorus and/or sulfur-containing structures. The reactivity of both heteroatoms, phosphorus and sulfur, is discussed by showing how they are involved as electrophilic, nucleophilic, or radicalar species in different transformations. The general methods for the preparation of phosphorothioates are described according to the various strategies involving P-S bond formation from one sulfur-reagent and one phosphorus-reagent, which include recent metalcatalyzed cross-coupling reactions. Particular attention is paid to synthetic applications of phosphorothioates occurring via the P-S bond cleavage, including for example anionic rearrangements and cascades, formation of sulfur-heterocycles, homolytic processes for olefins phosphorylation, and metal-catalyzed alkynes thiophosphorylation. The literature of the last two decades is covered, highlighting selected contributions in the chemistry of this class of compounds.

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