107394-76-3

Upstream product

• 673-32-5 1-Phenylprop-1-yne 
• 829-85-6 diphenylphosphane 
• 2327-99-3 1-phenylpropadiene 
• 65567-06-8 lithium diphenylphosphide 
• 678187-53-6 (tert-butyldimethylsilyl)diphenylphosphine 

Downstream Products

• 7302-07-0 diphenyl(1-phenylpropan-2-yl)phosphine oxide 
• 62556-17-6 (E)-diphenyl(1-phenylprop-1-en-2-yl)phosphine oxide 

Relevant academic research and scientific papers

Cobalt-catalyzed syn hydrophosphination of alkynes

Treatment of terminal and internal alkynes with diphenylphosphane in the presence of catalytic amounts of a base and cobalt (II) acetylacetonate affords, with perfect and universal syn selectivity, the (E)-alkenyldiphenylphosphane derivatives in good yiel

Hydrophosphination using [GeCl{N(SiMe3)2}3] as a pre-catalyst

Transformations catalyzed by germanium are scarce, with examples mainly limited to widely catalyzed processes such as polymerisation of lactide and hydroboration of carbonyls. Reported is the first example of hydrophosphination using a germanium pre-catalyst, yielding anti-Markovnikov products when diphenylphosphine is reacted with styrenes or internal alkynes at room temperature. This journal is

Photocatalytic Hydrophosphination of Alkenes and Alkynes Using Diphenylphosphine and Triamidoamine-Supported Zirconium

Reactions of alkene or alkyne with diphenylphosphine and catalytic [κ5-N,N,N,N,C-(Me3SiNCH2CH2)2NCH2CH2NSiMe2CH2]Zr (1) are greatly enhanced under photolysis, providing viable catalytic hydrophosphination with a broad substrate scope. Whereas diphenylphosphine had been an inaccessible substrate under thermal conditions, complete conversion of alkene substrates to tertiary phosphine is achieved in as little as four hours at ambient temperature with 1 under ultraviolet irradiation. Previously inactive alkenes are now hydrophosphination substrates with diphenylphosphine to produce tertiary phosphine ligands possessing tunable steric and electronic properties.

Regioselective Single and Double Hydrophosphination and Hydrophosphinylation of Unactivated Alkynes

A lanthanum-based N,N-dimethylbenzylamine complex was used as a precatalyst for both hydrophosphination and hydrophosphinylation of alkynes under mild conditions. In the case of hydrophosphination, the catalyst induced monoaddition with high regiospecific

Lithium-Aluminate-Catalyzed Hydrophosphination Applications

Synthesized, isolated, and characterized by X-ray crystallography and NMR spectroscopic studies, lithium phosphidoaluminate iBu3AlPPh2Li(THF)3 has been tested as a catalyst for hydrophosphination of alkynes, alkenes, and carbodiimides. Based on the collective evidence of stoichiometric reactions, NMR monitoring studies, kinetic analysis, and DFT calculations, a mechanism involving deprotonation, alkyne insertion, and protonolysis is proposed for the [iBu3AlHLi]2 aluminate catalyzed hydrophosphination of alkynes with diphenylphosphine. This study enhances further the development of transition-metal-free, atom-economical homogeneous catalysis using common sustainable main-group metals.

N-Heterocyclic Carbene Non-Innocence in the Catalytic Hydrophosphination of Alkynes

Studies on alkyne hydrophosphination employing nickel-NHC catalysts (NHC=N-heterocyclic carbene) revealed that the free N-alkyl substituted NHCs themselves were catalytically active. DFT calculations showed the mechanism involves the NHC acting as a Br?ns

Mechanistic Investigation of Well-Defined Cobalt Catalyzed Formal E-Selective Hydrophosphination of Alkynes

A formal E-selective hydrophosphination of terminal and internal alkynes catalyzed by a well-defined [Co(PMe3)4] (A) complex is achieved under mild conditions in good-to-excellent yield. The reaction does not require any additives and/or external base for an efficient hydrophosphination reaction. The reaction provided excellent scope and good functional tolerance. Detailed spectroscopic analysis (NMR, EPR, and UV-vis) revealed that the low valent cobalt(0) complex undergoes oxidative addition with diphenylphosphine, followed by hydrometalation with alkyne, and subsequent reductive elimination led to the expected product. The detailed spectroscopic analyses along with the isotopic labeled experiments facilitate to intercept the active intermediates that are involved in the catalytic cycle, which are detailed. It was revealed that the suprafacial (vide infra) delivery of H and phosphorus to π-alkynes in a syn-fashion led to formal E-vinyl phosphine.

Catalyst- and solvent-free hydrophosphination and multicomponent hydrothiophosphination of alkenes and alkynes

The hydrophosphination of carbon-carbon multiple bonds has been generally performed under acid, base or metal catalysis in different solvents. Herein, alkyl and alkenyl tertiary phosphines are obtained by the addition of diphenylphosphine to alkenes and alkynes, respectively, in the absence of a solvent and a catalyst. In the presence of elemental sulfur, the corresponding alkyl and alkenyl tertiary phosphine sulfides are synthesized in a three-component process. These simple methods, which meet most of the principles of Green Chemistry, are highly regioselective towards the anti-Markovnikov products and diastereoselective towards the Z alkenyl phosphines. The mechanistic aspects of the reactions are also tackled and the efficiency of the latter is compared with that of the catalytic methods.

Synthesis of calcium and ytterbium complexes supported by a tridentate imino-amidinate ligand and their application in the intermolecular hydrophosphination of alkenes and alkynes

Well-defined calcium and ytterbium complexes [{2-NC(Ph)NArC 6H4CHNAr}M{N(SiMe3)2}(THF)] (M = Ca, Yb; Ar = 2,6-iPr2C6H3) have been synthesized and characterized. They catalyze the

Catalytic synthesis of vinylphosphanes via calcium-mediated intermolecular hydrophosphanylation of alkynes and butadiynes

The calcium complex [(thf)4Ca(PPh2)2] (1) is a very effective catalyst for the hydrophosphanylation of substituted alkynes of the type R-CC-R (R = Me, Ph) yielding (E)-1,2-diphenyl-1- diphenylphosphanylethene (2a) and (Z)-