281199-46-0

Upstream product

• 16352-18-4 4,4,5,5-tetramethyl<1,3,2>dioxaphospholane-2-oxide 
• 829-85-6 diphenylphosphane 
• 100-42-5 styrene 

Downstream Products

• 502494-93-1 (1-benzyl-2-ethyl-2-hydroxy-butyl)-phosphonic acid benzyl ester methyl ester 
• 502494-96-4 (1-benzyl-2-hydroxy-4-phenyl-butyl)-phosphonic acid tert-butyl ester methyl 
• 502494-88-4 phenethyl-phosphonic acid benzyl ester methyl ester 
• 502494-90-8 phenethyl-phosphonic acid tert-butyl ester methyl ester 
• 40939-59-1 pent-2-ene-1,5-diyldibenzene 
• 502494-87-3 phenylethyl-phosphonic acid monomethyl ester 

Relevant academic research and scientific papers

Regio- and enantioselective catalytic hydrophosphorylation of vinylarenes

Regioselective and stereoselective hydrophosphorylation of vinylarenes 1 with pinacol H-phosphonate 2 can be achieved with transition metal catalysts. The use of rhodium catalysts such as the Wilkinson complex leads to the anti-Markovnikov adducts 3 as the only observable reaction products. In contrast, palladium catalysts give high selectivities for the Markovnikov adducts 4. In the presence of (R,S)-BINAPHOS as a chiral ligand, significant enantioselectivities have been obtained for the first time in hydrophosphorylation reactions.

Palladium-catalyzed hydrophosphonylation of alkenes with dialkyl H-phosphonates

The palladium-catalyzed hydrophosphonylation of alkenes with previously unreactive acyclic dialkyl H-phosphonates has been developed. A catalyst system based on palladium/DavePhos or palladium/SPhos enables the transformation of various alkenes to phospho

A new class of 3′-sulfonyl binaphos ligands: Modulation of activity and selectivity in asymmetric palladium-catalysed hydrophosphorylation of styrene

Palladium-catalysed monophosphorylation of (R)-2,2′- bisperfluoroalkanesulfonates of BINOL (RF = CF3 or C 4F9) by a diaryl phosphinate [Ar2P(O)H] followed by phosphine oxide reduction (Cl3SiH) then lithium diisopropylamide-mediated anionic thia-Fries rearrangement furnishes enantiomerically-pure (R)-2′-diarylphosphino-2′-hydroxy-3′- perfluoralkanesulfonyl-1,1′-binaphthalenes [(R)-8ab and (R)-8g-j], which can be further diversified by Grignard reagent (RMgX)-mediated CF 3-displacement [→(R)-8c-f]. Coupling of (R)-8a-j with (S)-1,1′-binaphthalene-2,2′-dioxychlorophosphine (S)-9 generates 3′-sulfonyl BINAPHOS ligands (R,S)-10a-j in good yields (43-82%). These new ligands are of utlility in the asymmetric hydrophosphonylation of styrene (1) by 4,4,5,5-tetramethyl-1,3,2-dioxaphospholane 2-oxide (2), for which a combination of the chiral ligands with either [Pd(Cp)(allyl)] or [Pd(allyl)(MeCN)2]+/NaCH(CO2Me)2 proves to be a convenient and active pre-catalyst system. A combination of an electron-rich phosphine moiety and an electron-deficient 3′-sulfone moiety provides the best enantioselectivity to date for this process, affording the branched 2-phenethenephosphonate, (-)-iso-3, in upto 74% ee with ligand (R,S)-10i, where Ar=p-anisyl and the 3′-SO2R groupis triflone.

t-BuOK-catalyzed addition phosphines to functionalized alkenes: A convenient synthesis of polyfunctional phosphine derivatives

The use of t-BuOK in DMSO allows a smooth addition of Ph2PH, Cy2PH and Ph2P(O)H to various functionalized alkenes leading to polyfunctional phosphines in good yields. This method has been used to prepare precursors for P,P- and P,N-ligands.