Deoxofluorination Reactions Using N,N-Disubstituted Aminodifluorosulfinium Tetrafluoroborate Salts

Mahé, Olivier; L’Heureux, Alexandre; Couturier, Michel; Bennett, C. W.; Clayton, Simon; Tovell, David J.; Beaulieu, Françis; Paquin, Jean‐François

doi:10.1016/j.jfluchem.2013.05.019

Cited by 18 publications

(7 citation statements)

References 18 publications

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“…SF 3 complexes are very rare, but the hydrolysis of 11 as well as the reaction with a Lewis acid is in accordance with the behavior of other transition metal or organo substituted λ 4 ‐trifluorosulfanyl units. [5c], [5e], [7a], [7c], …”

Section: Discussionmentioning

confidence: 99%

Synthesis and Reactivity of Iridium(I) Fluorido Complexes: Oxidative Addition of SF₄ at trans‐[Ir(F)(CO)(PEt₃)₂]

Pfister

Bui

Braun

et al. 2020

Zeitschrift anorg allge chemie

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The facile access to the Vaska type fluorido complexes trans‐[Ir(F)(CO)(PR3)2] [6: R = Et, 7: R = Ph, 8: R = iPr, 9: R = Cy, 10: R = tBu] was achieved by halide exchange at trans‐[Ir(Cl)(CO)(PR3)2] (1–5) with Me4NF. Furthermore, the reaction of complex 6 with SF4 gave cis,trans‐[Ir(F)2(SF3)(CO)(PEt3)2] (11), whereas 8–10 did not react. Reactivity studies revealed that 11 can selectively be manipulated at the sulfur atom by hydrolysis or fluoride abstraction to give cis,trans‐[Ir(F)2(SOF)(CO)(PEt3)2] (12) and cis,trans‐[Ir(F)2(SF2)(CO)(PEt3)2][AsF6] (13), respectively.

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Section: Discussionmentioning

confidence: 99%

Synthesis and Reactivity of Iridium(I) Fluorido Complexes: Oxidative Addition of SF₄ at trans‐[Ir(F)(CO)(PEt₃)₂]

Pfister

Bui

Braun

et al. 2020

Zeitschrift anorg allge chemie

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“…Other reagents used or evaluated for the aforementioned deoxofluorinations included morphDAST, [517] bis(2-methoxyethyl)aminosulfur trifluoride (Deoxo-Fluor) with [518,519] or without [520,521] BF 3 • Et 2 O, 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride, [522] and XtalFluor-E or XtalFluor-M -Et 3 N • 3HF. [203,506,523,524] Synthesis of 4,4-difluorocycloheptanone relied on the ring expansion in compound 110 with trimethylsilyldiazomethane or ethyl diazoacetate. [509,512]…”

Section: 3-and 44-difluorocycloalkyl-substituted Building Blocksmentioning

confidence: 99%

Emerging Building Blocks for Medicinal Chemistry: Recent Synthetic Advances

2021

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Current medicinal chemistry relies heavily on the quality of building blocks, i. e. reagents used to introduce chemical diversity into the target molecules. The last decade witnessed an emergence of many novel (or well-overlooked old) chemotypes for drug discovery, which is related to adapting new synthetic methodologies, designing new sp 3 -enriched bioisosteres, paying attention to previously underrated (or even unwanted) structural motifs, or combination thereof. In this review with 532 references, a survey of selected chemotypes that emerged recently in medicinal chemistry is provided, with a focus on the synthesis of the corresponding building blocks. Thus, saturated (hetero)aliphatic boronates, sulfonyl fluorides, sulfinates, non-classical sp 3 -enriched benzene isosteres, bicyclic morpholine/piperidine/piperazine analogs, as well as gemdifluorinated cycloalkanes (as an example of emerging fluorinated motifs) are discussed.

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“…29,30 Paquin and co-workers have synthesized a variety of new analogues of these salt-based reagents (e.g., 57-59, Scheme 17). 31 However, none of these new variants exhibit superior reactivity in deoxyfluorination reactions compared to XtalFluor-M or XtalFluor-E.…”

Section: Scheme 16mentioning

confidence: 99%

Recent Developments in the Deoxyfluorination of Alcohols and Phenols: New Reagents, Mechanistic Insights, and Applications

Hu²,

Hunter

2017

Synthesis

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This short review describes the development of new reagents and methods for the deoxyfluorination of phenols and alcohols during the period of 2011 to 2017. Important advances in the mechanistic understanding of these processes are discussed. The continuing importance of deoxyfluorination chemistry for the synthesis of valuable target molecules is highlighted through case studies including examples of 18F-radiosynthesis and the preparation of exotic multifluorinated compounds.1 Introduction2 New Deoxyfluorination Reagents3 Novel Applications of ‘Legacy’ Deoxyfluorinating Reagents4 Conclusions and Future Directions

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Deoxofluorination Reactions Using N,N-Disubstituted Aminodifluorosulfinium Tetrafluoroborate Salts

Cited by 18 publications

References 18 publications

Synthesis and Reactivity of Iridium(I) Fluorido Complexes: Oxidative Addition of SF₄ at trans‐[Ir(F)(CO)(PEt₃)₂]

Synthesis and Reactivity of Iridium(I) Fluorido Complexes: Oxidative Addition of SF₄ at trans‐[Ir(F)(CO)(PEt₃)₂]

Emerging Building Blocks for Medicinal Chemistry: Recent Synthetic Advances

Recent Developments in the Deoxyfluorination of Alcohols and Phenols: New Reagents, Mechanistic Insights, and Applications

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Deoxofluorination Reactions Using N,N-Disubstituted Aminodifluorosulfinium Tetrafluoroborate Salts

Cited by 18 publications

References 18 publications

Synthesis and Reactivity of Iridium(I) Fluorido Complexes: Oxidative Addition of SF4 at trans‐[Ir(F)(CO)(PEt3)2]

Synthesis and Reactivity of Iridium(I) Fluorido Complexes: Oxidative Addition of SF4 at trans‐[Ir(F)(CO)(PEt3)2]

Emerging Building Blocks for Medicinal Chemistry: Recent Synthetic Advances

Recent Developments in the Deoxyfluorination of Alcohols and Phenols: New Reagents, Mechanistic Insights, and Applications

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Synthesis and Reactivity of Iridium(I) Fluorido Complexes: Oxidative Addition of SF₄ at trans‐[Ir(F)(CO)(PEt₃)₂]

Synthesis and Reactivity of Iridium(I) Fluorido Complexes: Oxidative Addition of SF₄ at trans‐[Ir(F)(CO)(PEt₃)₂]