- Diverse C-P Cross-Couplings of Arylsulfonium Salts with Diarylphosphines via Selective C-S Bond Cleavage
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Diverse C-P cross-couplings of arylthianthrenium salts with diarylphosphines producing various triarylphosphines via highly selective C-S bond cleavage are reported. In the absence of catalyst, the reaction of arylthianthrenium salts with diarylphosphines undergoes phosphinative ring opening exclusively via the cleavage of an endocyclic C-S bond of a thianthrene skeleton. The use of a palladacycle catalyst under otherwise the same conditions enables the phosphination via the cleavage of an exocyclic C-S bond with significantly higher speed.
- Ye, Yun,Zhu, Jie,Huang, Yinhua
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p. 2386 - 2391
(2021/04/05)
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- Pd-Catalyzed P–C Cross-Coupling of Aryl Bromides and Triflates with Hydroxymethylphosphine Sulfide Derivatives
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The development of a versatile process for phosphine synthesis has attracted considerable interest because organophosphines are indispensable for organic synthesis. Previously, we developed a Pd-catalyzed P–C coupling reaction for hydroxymethylphosphine s
- Ohta, Hidetoshi,Xue, Qian,Hayashi, Minoru
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supporting information
p. 735 - 738
(2018/02/21)
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- Pd-catalyzed P-C cross-coupling reactions for versatile triarylphosphine synthesis
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Practical and versatile syntheses of tertiary phosphine derivatives have been achieved by palladium-catalyzed deformylative P-C cross-coupling reactions of hydroxymethylphosphine derivatives. Sequential couplings of orthogonally protected precursors provide a simple and practical route toward a variety of tertiary phosphine derivatives having aryl substituents in any combination.
- Hayashi, Minoru,Matsuura, Takashi,Tanaka, Ippei,Ohta, Hidetoshi,Watanabe, Yutaka
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supporting information
p. 628 - 631
(2013/04/11)
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- The Kinetics and Mechanism of the Reaction of Tricoordinate Phosphorus Compounds with Diaryl Trisulfides
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Kinetic data and activation parameters are reported for the reaction of a series of tricoordinate phosphorus compounds, , with diaryl trisulfides.The second-order rate coefficients for series of arylphosphines, phosphinites and phosphonites, correlate with the Hammett ? constants of the aryl substituents with ρ values of -1.1, -1.1 and -1.1 respectively and these results are discussed in terms of a biphilic mechanism analogous to that proposed for the reaction of tricoordinate phosphorus with S8.
- Hall, C. Dennis,Tweedy, Bruce R.,Kayhanian, Robert,Lloyd, John R.
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p. 775 - 779
(2007/10/02)
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- Kinetics and mechanism of the reaction of trico-ordinate phosphorus ompounds with octasulphur
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Kinetic data and activation parameters are reported for the reactions of a series of phosphites, arylphosphonites, diarylphosphinites, and triarylphosphines with octasulphur (S8) in toluene as solvent.For the phosphites the data are explained in terms of changes in p-character of the Ione-pair orbital on phosphorus and inductive electron donation by the alkyl groups.The rates of reaction of series of arylphosphonites, diarylphosphonites, and triarylphosphones correlate with the Hammett ? constants to give ? values of -3.0, -3.0, and -2.5, respactively, and the results are discussed in terms of the Reactivity-Selectivity Principle and the biphilic mechanism or insertion of trico-ordinate phosphorus into ?-bonds.
- Lloyd, John R.,Lowther, Nicholas,Zsabo, G.,Hall, C. Dennis
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p. 1813 - 1818
(2007/10/02)
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