Reaction Between Triphenylphosphine and Acetylenic Esters or Acetylenic Ketones in the Presence of Mercaptoesters

Mosslemin, Mohammad Hossein; Anary-Abbassinejad, Mohammad; Hassanabadi, Alireza; Mohebat, Marzieh; Nateghi, Mohammad Reza

doi:10.1080/00397910902778027

Cited by 5 publications

(2 citation statements)

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“…Although the reaction was efficient, only a limited substrate scope was disclosed. The results led, however, to subsequent publications describing the use of 2-mercaptoacetate 785 and 4-methyleneoxetan-2-one 786 as alternative pronucleophiles.…”

Section: Chemical Reviewsmentioning

confidence: 99%

Phosphine Organocatalysis

et al. 2018

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The hallmark of nucleophilic phosphine catalysis is the initial nucleophilic addition of a phosphine to an electrophilic starting material, producing a reactive zwitterionic intermediate, generally under mild conditions. In this Review, we classify nucleophilic phosphine catalysis reactions in terms of their electrophilic components. In the majority of cases, these electrophiles possess carbon–carbon multiple bonds: alkenes (section 2), allenes (section 3), alkynes (section 4), and Morita–Baylis–Hillman (MBH) alcohol derivatives (MBHADs; section 5). Within each of these sections, the reactions are compiled based on the nature of the second starting material—nucleophiles, dinucleophiles, electrophiles, and electrophile–nucleophiles. Nucleophilic phosphine catalysis reactions that occur via the initial addition to starting materials that do not possess carbon–carbon multiple bonds are collated in section 6. Although not catalytic in the phosphine, the formation of ylides through the nucleophilic addition of phosphines to carbon–carbon multiple bond–containing compounds is intimately related to the catalysis and is discussed in section 7. Finally, section 8 compiles miscellaneous topics, including annulations of the Hüisgen zwitterion, phosphine-mediated reductions, iminophosphorane organocatalysis, and catalytic variants of classical phosphine oxide–generating reactions.

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Section: Chemical Reviewsmentioning

confidence: 99%

Phosphine Organocatalysis

et al. 2018

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“…Recently, we reported the reaction of acetylene dicarboxylic diester with 1,1,1-trifluorobutane-2,4-dione in the presence of triphenylphosphine for the synthesis of trifluoromethylated cyclobutene derivatives. 10 In continuation of our previous work on the reaction between trivalent phosphorus nucleophiles in the presence of acidic organic compounds, [10][11][12] we report here the results of our studies on the reaction between ethyl phenylpropiolate and triphenylphosphine in the presence of 1,1,1-trifluorobutane-2,4-dione derivatives 1.…”

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confidence: 84%