Synthesis of γ-butyrolactones containing α,α-difluoromethylenyl bisphosphonate initiated by Na2S2O4

Yang, Xueyan; Zhu, Yaoping; Fang, Xiang; Yang, Xianjin; Wu, Fanhong; Shen, Yongjia

doi:10.1016/j.jfluchem.2006.11.009

Cited by 13 publications

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“…Alternatively, sodium dithionite, Na 2 S 2 O 4 , can be used as a radical initiator in an aqueous medium. This variation was employed by Shen and co‐workers to prepare CF 2 ‐phosphonate‐containing γ‐butyrolactones 53 from diethyl iododifluoromethylphosphonate and 4‐pentenoic acids 52 in an alkaline medium in one step (Scheme 20B) [96] …”

Section: Synthetic Methodsmentioning

confidence: 99%

Recent Advances in Synthesis of Difluoromethylene Phosphonates for Biological Applications

et al. 2021

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For almost 40 years, difluoromethylene phosphonates have proven to be versatile molecular tools in biochemical studies owing to their close resemblance to naturally occurring phosphates and phosphonates. As bioisosteric, non‐hydrolyzable analogs of these essential molecules, difluoromethylene phosphonates can target the critical parts of the cellular machinery and therefore exhibit a diverse spectrum of biological activity. In the past ten years, there have appeared many new methods for the synthesis of difluoromethylene phosphonates. Most notably, photoredox catalysis has firmly entered the field, while cross‐coupling and nucleophilic strategies have met considerable elaboration and refinement, entirely in accord with the current trends in synthetic organic chemistry. Herein, we introduce difluoromethylene phosphonates as a distinct, high‐tech subclass of synthetic phosphonates resulting from the research efforts on the cross‐section of organophosphorus, organofluorine, and bioorganic chemistry. We then proceed to the discussion of general methods for the preparation of difluoromethylene phosphonates, comprehensively reviewing reactions developed in the past 15 years while providing the context of earlier works where appropriate. Finally, we present selected examples of molecules with high biological activity, their biological targets, and the synthetic steps employed for their preparation.

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Section: Synthetic Methodsmentioning

confidence: 99%

Recent Advances in Synthesis of Difluoromethylene Phosphonates for Biological Applications

et al. 2021

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“…Recently, the method has been extended to the synthesis of g-butyrolactones through the addition of the phosphonodifluoromethyl radical onto 4-pentenoic acids. 8 Except this example, no general study of the addition of the phosphonodifluoromethyl radical, generated from the iodophosphonate, onto alkenes has been reported in the literature.…”

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confidence: 98%

Radical Conjugated Addition: Addition of Dialkyl Phosphonodifluoromethyl Radical onto Unsaturated Ketones

Sene¹,

Diab²,

Hienzsch³

et al. 2009

Synlett

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Synthesis of γ‐Butyrolactones Containing α,α‐Difluoromethylenyl Bisphosphonate Initiated by Na₂S₂O₄.

et al. 2007

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Synthesis of γ-butyrolactones containing α,α-difluoromethylenyl bisphosphonate initiated by Na2S2O4

Cited by 13 publications

References 23 publications

Recent Advances in Synthesis of Difluoromethylene Phosphonates for Biological Applications

Recent Advances in Synthesis of Difluoromethylene Phosphonates for Biological Applications

Radical Conjugated Addition: Addition of Dialkyl Phosphonodifluoromethyl Radical onto Unsaturated Ketones

Synthesis of γ‐Butyrolactones Containing α,α‐Difluoromethylenyl Bisphosphonate Initiated by Na₂S₂O₄.

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Synthesis of γ-butyrolactones containing α,α-difluoromethylenyl bisphosphonate initiated by Na2S2O4

Cited by 13 publications

References 23 publications

Recent Advances in Synthesis of Difluoromethylene Phosphonates for Biological Applications

Recent Advances in Synthesis of Difluoromethylene Phosphonates for Biological Applications

Radical Conjugated Addition: Addition of Dialkyl Phosphonodifluoromethyl Radical onto Unsaturated Ketones