Palladacycle promoted asymmetric hydrophosphination of α,β-unsaturated sulfonyl fluorides

Li, Xirui; Chen, Houguang Jeremy; Wang, Weifan; Ma, Mengtao; Chen, Yu; Li, Yongxin; Pullarkat, Sumod A.; Leung, Pak‐Hing

doi:10.1016/j.jorganchem.2019.120912

Cited by 16 publications

(8 citation statements)

References 34 publications

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“…In 2019, Leung and co-workers reported Pd-catalyzed asymmetric hydrophosphinations of α,β-unsaturated sulfonyl fluorides ( 51 ) ( Scheme 12 a). 51 Their mechanistic investigations were consistent with the hypothesis that the sulfonyl group chelates to the palladium catalyst ( 53 ) via the sulfonyl oxygens. The resulting chelated intermediate facilitates the intramolecular nucleophilic addition of the phosphine to the olefin.…”

Section: Catalytic Activation Of S(vi) Fluoridessupporting

confidence: 69%

The Emerging Applications of Sulfur(VI) Fluorides in Catalysis

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Section: Catalytic Activation Of S(vi) Fluoridessupporting

confidence: 69%

The Emerging Applications of Sulfur(VI) Fluorides in Catalysis

et al. 2021

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“…Thus, the most recognizable feature of ESF ( 39) is its welldefined reactivity towards nucleophiles as "the most perfect Michael acceptor ever found" (Scheme 33). [180] The list of nucleophiles used in the Michael reactions with alkenyl sulfonyl fluorides include aromatic [291] or aliphatic [309] amines, azide, [164] triazoles, [286] thiols or sulfinates, [291] HP(O)Me 2 , [336] active methylene compounds, [291] and pyrroles. [180] Among the CÀ C bond-forming reactions, visible-lightpromoted radical additions to ESF (39) should be outlined, such as decarboxylative addition of NHPI redox-active esters 9, Scheme 34) [337] or Mn 2 (CO) 10 -catalyzed reductive addition of alkyl iodides.…”

Section: Synthesis Of Saturated Sulfonyl Fluoridesmentioning

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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“…48 In 2019, Leung and coworkers developed the first phosphapalladacycle-catalyzed asymmetric hydrophosphination of 2-arylethenesulfonyl fluorides (Scheme 35). 49 A series of chiral sulfonyl fluoride derived phosphines were prepared in quantitative yields with up to 93% ee.…”

Section: Scheme 32 a Ni-catalyzed Annulative Sufex Process For The Symentioning

confidence: 99%

Ethenesulfonyl Fluoride (ESF) and Its Derivatives in SuFEx Click Chemistry and More

et al. 2019

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The sulfur(VI) fluoride exchange reaction (SuFEx), developed by Sharpless and co-workers in 2014, is a new category of click reaction that creates molecular connections with absolute reliability and unprecedented efficiency through a sulfur(VI) hub. Ethenesulfonyl fluoride (ESF), as one of the most important sulfur(VI) hubs, exhibits extraordinary reactivity in SuFEx click chemistry and organic synthesis. This review summarizes the chemical properties and applications of ESF in click chemistry, organic chemistry, materials science, medicinal chemistry and in many other fields related to organic synthesis.1 Introduction2 Chemical Transformations of ESF3 Chemical Transformations of 2-Arylethenesulfonyl Fluorides4 Novel SuFEx Reagents Derived from ESF5 Applications of ESF Derivatives in Medicinal Chemistry6 Applications of ESF Derivatives in Materials Science7 Conclusion

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Palladacycle promoted asymmetric hydrophosphination of α,β-unsaturated sulfonyl fluorides

Cited by 16 publications

References 34 publications

The Emerging Applications of Sulfur(VI) Fluorides in Catalysis

The Emerging Applications of Sulfur(VI) Fluorides in Catalysis

Emerging Building Blocks for Medicinal Chemistry: Recent Synthetic Advances

Ethenesulfonyl Fluoride (ESF) and Its Derivatives in SuFEx Click Chemistry and More

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