The Addition of Dialkyl Phosphites and Diphenylphosphine Oxide on the Triple Bond of Dimethyl Acetylenedicarboxylate under Solvent-Free and Microwave Conditions

Keglevich, György; Bálint, Erika; Takacs, J. M.; Drahos, László; Huben, Krzysztof; Jankowski, Stefan

doi:10.2174/1570179411999140304142747

Cited by 16 publications

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“…Treatment of 13 with HP(O)(OEt) 2 does indeed generate 5 and the vinyl phosphonate (90 °C, 20 h). However, the development of a catalytic process was hindered by the observation that an uncatalyzed double-addition reaction occurs between DMAD and HP(O)(OEt) 2 (2 equiv) under the insertion conditions (80 °C, 2 days) . A successful catalytic approach needs to circumvent this background reaction.…”

Section: Resultsmentioning

confidence: 99%

Syn-Insertion of Alkynes into Gold–Phosphito Bonds: Stereoselectivity and Reversible Protodeauration

et al. 2021

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The susceptibility of gold phosphito compounds to undergo alkyne insertion into gold–phosphorus bonds has been investigated. An electron-deficient alkyne (DMAD) underwent syn-insertion into the gold–phosphorus bond to generate a Z-vinylgold species, whereas electron-rich internal alkynes were unreactive. When a P-chiral phosphinate was used as a probe, the protodeauration and insertion steps were found to be stereospecific. In contrast to the insertion chemistry observed with DMAD, electron-deficient terminal alkynes generated alkynylgold compounds and released secondary phosphites through a reversible protodeauration process.

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Section: Resultsmentioning

confidence: 99%

Syn-Insertion of Alkynes into Gold–Phosphito Bonds: Stereoselectivity and Reversible Protodeauration

et al. 2021

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“…MW addition was useful to enhance the addition of dialkyl phosphites, ethyl phenyl‐ H ‐phosphinate and diphenylphosphine oxide to the more reactive double‐bond of N ‐phenyl and N ‐methylmaleimide, as well as maleic anhydride . The addition of two equivalents of >P(O)H species to dimethyl acetylenedicarboxylate and analogous derivatives was also studied …”

Section: Reactions Taking Place More Efficiently Under Mw Conditionsmentioning

confidence: 99%

The Impact of Microwaves on Organophosphorus Chemistry

Keglevich

2018

The Chemical Record

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A personal account on the pioneering results on microwave (MW)-assisted organophosphorus syntheses obtained in the last decade is presented. The broad spectrum of the reactions studied exemplifies the advantages of the MW technique as a green tool regarding efficiency and the simplification of catalyst systems. Theoretical calculations for a few typical models helped us to explore the scope and limitations of the application of MW irradiation.

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“…Products 39 and 40 were obtained, with one exception, in good yields. Depending on the molar ratio of the reactants and the conditions (temperature and reaction time), the addition of dialkyl phosphites or diphenylphosphine oxide to the triple bond of dimethyl acetylenedicarboxylate resulted in the formation of a comparable mixture of the corresponding monoadduct (41) and bisadduct (42), or the bisadduct (42) as the predominating or exclusive product (Scheme 3.29, Table 3.7) [61].…”

Section: -86%mentioning

confidence: 99%

The Use of MW in Organophosphorus Chemistry

Keglevich

Bálint²,

Kiss

2016

SpringerBriefs in Molecular Science

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The third chapter summarizes a special field, the application of the microwave (MW) technique in the synthesis of organophosphorus compounds. On the one hand, reactions are shown that are otherwise rather reluctant on traditional thermal heating. On the other hand, reactions are discussed, which, became more efficient (shorter reaction times and higher yields) on MW irradiation. Finally, the simplification of catalytic systems under MW conditions are surveyed.

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The Addition of Dialkyl Phosphites and Diphenylphosphine Oxide on the Triple Bond of Dimethyl Acetylenedicarboxylate under Solvent-Free and Microwave Conditions

Cited by 16 publications

References 0 publications

Syn-Insertion of Alkynes into Gold–Phosphito Bonds: Stereoselectivity and Reversible Protodeauration

Syn-Insertion of Alkynes into Gold–Phosphito Bonds: Stereoselectivity and Reversible Protodeauration

The Impact of Microwaves on Organophosphorus Chemistry

The Use of MW in Organophosphorus Chemistry

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