13685-71-7

Upstream product

• 5952-49-8 (2-phenylethyl)diphenylphosphane 
• 100-42-5 styrene 
• 6591-07-7 diphenylphosphane sulfide 
• 17154-34-6 (trimethylsilyl)diphenylphosphine 
• 829-85-6 diphenylphosphane 

Relevant academic research and scientific papers

Vic-Diphosphination of Alkenes with Silylphosphine under Visible-Light-Promoted Photoredox Catalysis

An Ir(ppy)3-catalyzed vic-diphosphination of styrenes with Me3Si-PPh2 and NFSI proceeds under blue LED irradiation to afford the corresponding bis(diphenylphosphino)ethane derivatives without any formation of hydrophosphination byproducts, which are inevitable and problematic under the previous Cu/NHC catalysis. Additionally, the visible-light-promoted photoredox catalysis enables the diphosphination of relatively challenging aliphatic alkenes and β-substituted styrene.

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.

Straightforward Solvent-Free Synthesis of Tertiary Phosphine Chalcogenides from Secondary Phosphines, Electron-Rich Alkenes, and Elemental Sulfur or Selenium

A series of tertiary phosphine sulfides and selenides have been synthesized in excellent yields (88-99%) via a three-component reaction between secondary phosphines, electron-rich alkenes (styrene, vinyl chalcogenides), and elemental sulfur or selenium, proceeding under solvent-free conditions (80-82C, 4-44 h). The interaction occurs via initial oxidation of secondary phosphines with elemental sulfur or selenium followed by noncatalyzed anti-Markovnikov addition of the generated R2P(E)H (E = S, Se) species to alkenes to afford the corresponding adducts with high chemo- and regioselectivity.

Copper-Catalyzed Vicinal Diphosphination of Styrenes: Access to 1,2-Bis(diphenylphosphino)ethane-Type Bidentate Ligands from Olefins

A copper/N-heterocyclic carbene (NHC) catalyzed oxidative vicinal diphosphination of styrenes with diphenyl(trimethylsilyl)phosphine proceeds in the presence of LiOtBu and a pyridine N-oxide/MnO2combined oxidant to deliver the corresponding 1,2-bis(diphenylphosphino)ethanes (DPPEs) in good yields. The present copper catalysis can provide access to the DPPE-type ligands directly from the relatively simple alkenes.

nBuLi-mediated hydrophosphination: A simple route to valuable organophosphorus compounds

A straightforward synthesis of homoallyl- and allylphosphanes has been developed using nBuLi-mediated hydrophosphination of conjugated dienes. In all the cases the phosphorus atom of the reacting phosphane attacked the sterically less demanding side of the diene exclusively. In addition, high regioselectivities towards 1,2- or 1,4-addition products were observed depending on the nature of the dienes. This hydrophosphination reaction was extended to a variety of substrates such as styrene derivatives, alkynes and 1,3,5-cycloheptatriene. The structures of three hydrophosphination products were confirmed by X-ray diffraction studies.

First titanium-catalyzed 1,4-hydrophosphination of 1,3-dienes

"Chemical Equation Presented" Titanium complexes outshine other catalysts: Titanium complexes have been found to catalyze 1,4-hydrophosphination of dienes, which is thought to proceed through an allyl intermediate (see scheme). Unprecedented regioselectivities (1,4- vs. 1,2-) are reached by using [TiCp2(PMe3)2] or a titanocene complex bearing a pendant phosphine tether as catalysts.

Radical addition reactions of diphenylphosphine sulfide

Radical additions of diphenylphosphine sulfide [Ph2P(S)H] to various C=C bonds offers a general, mild and efficient approach to alkyl(diphenyl)phosphine sulfides. Georg Thieme Verlag Stuttgart.