Rhodium-catalyzed synthesis of 1-alkynylphosphine oxides from 1-alkynes and tetraphenylbiphosphine

Arisawa, Mieko; Onoda, Masato; Hori, Chieko; Yamaguchi, Masahiko

doi:10.1016/j.tetlet.2006.04.158

Cited by 35 publications

(13 citation statements)

References 12 publications

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“…The reactions of 1-alkynes with tetraphenyldiphosphine are catalyzed by RhH(PPh 3 ) 4 under reflux in toluene to provide mixtures of 1-alkynylphosphines and their oxides in the presence of a stoichiometric amount of nitrobenzene (Scheme 22). 24 Scheme 22 Rhodium-catalyzed synthesis of 1-alkynylphosphine oxides from 1-alkynes and tetraphenyldiphosphine…”

Section: Arisawamentioning

confidence: 99%

Transition-Metal-Catalyzed Synthesis of Organophosphorus Compounds Involving P–P Bond Cleavage

Arisawa

2020

Synthesis

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Organophosphorus compounds are used as drugs, pesticides, detergents, food additives, flame retardants, synthetic reagents, and catalysts, and their efficient synthesis is an important task in organic synthesis. To synthesize novel functional organophosphorus compounds, transition-metal-catalyzed methods have been developed, which were previously considered difficult because of the strong bonding that occurs between transition metals and phosphorus. Addition reactions of triphenylphosphine and sulfonic acids to unsaturated compounds in the presence of a rhodium or palladium catalyst lead to phosphonium salts, in direct contrast to the conventional synthesis involving substitution reactions of organohalogen compounds. Rhodium and palladium complexes catalyze the cleavage of P–P bonds in diphosphines and polyphosphines and can transfer organophosphorus groups to various organic compounds. Subsequent substitution and addition reactions proceed effectively, without using a base, to provide various novel organophosphorus compounds.1 Introduction2 Transition-Metal-Catalyzed Synthesis of Phosphonium Salts by Addition Reactions of Triphenylphosphine and Sulfonic Acids3 Rhodium-Catalyzed P–P Bond Cleavage and Exchange Reactions4 Transition-Metal-Catalyzed Substitution Reactions Using Diphosphines4.1 Reactions Involving Substitution of a Phosphorus Group by P–P Bond Cleavage4.2 Related Substitution Reactions of Organophosphorus Compounds4.3 Substitution Reactions of Acid Fluorides Involving P–P Bond Cleavage of Diphosphines5 Rhodium-Catalyzed P–P Bond Cleavage and Addition Reactions6 Rhodium-Catalyzed P–P Bond Cleavage and Insertion Reactions Using Polyphosphines7 Conclusions

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Section: Arisawamentioning

confidence: 99%

Transition-Metal-Catalyzed Synthesis of Organophosphorus Compounds Involving P–P Bond Cleavage

Arisawa

2020

Synthesis

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“…Diphosphines were also applied to C(sp)-P cross-coupling reactions with terminal alkynes under rhodium catalysis in the presence of nitrobenzenes (Scheme 50). 150 Nitrobenzene is crucial in this reaction and is assumed to activate the diphosphine.…”

Section: C(sp)-p Cross-couplingmentioning

confidence: 99%

Transition-Metal-Catalyzed C-P Cross-Coupling Reactions

Tappe¹,

Trepohl²,

Oestreich³

2010

Synthesis

100

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This review is a comprehensive account of transitionmetal-catalyzed cross-coupling reactions to form C-P bonds. Organized according to the hybridization of the carbon coupling partner, the numerous phosphorus coupling partners are discussed individually. The several putative mechanisms of these transition-metal catalyses are also included, thereby providing insights into both the synthetic and the mechanistic aspects of this chemistry. A separate section is devoted to asymmetric C-P cross-couplings. 2.7.

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“…5 As for the latter, the rhodium-catalyzed reaction of 1-alkynes and tetraphenyldiphosphine in the presence of a nitrobenzene gave 1-phosphinoyl-1-alkynes. 6 This reaction proceeded via the metal-catalyzed addition of the P-P bond with the nitrobenzene followed by the C-H substitution of the 1-alkyne. We considered the P-P bond cleavage method by transition metal catalysis to be attractive, because such reaction can be extended to the development of organophosphorus synthesis using inexpensive elemental phosphorus.…”

Section: Introductionmentioning

confidence: 99%

Rhodium-catalyzed thiophosphinoylation reaction of 1,2-dienes with diphosphine disulfides

Arisawa

Yamaguchi

2009

Tetrahedron Letters

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Rhodium-catalyzed synthesis of 1-alkynylphosphine oxides from 1-alkynes and tetraphenylbiphosphine

Cited by 35 publications

References 12 publications

Transition-Metal-Catalyzed Synthesis of Organophosphorus Compounds Involving P–P Bond Cleavage

Transition-Metal-Catalyzed Synthesis of Organophosphorus Compounds Involving P–P Bond Cleavage

Transition-Metal-Catalyzed C-P Cross-Coupling Reactions

Rhodium-catalyzed thiophosphinoylation reaction of 1,2-dienes with diphosphine disulfides

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