1190882-69-9

Upstream product

• 100-52-7 benzaldehyde 
• 536-74-3 phenylacetylene 
• 128812-07-7 (R)-1,3-diphenylprop-2-yn-1-ol 
• 1817-49-8 1,3-diphenyl-1-propyn-3-ol 
• 4559-70-0 Diphenylphosphine oxide 
• 1079-66-9 chloro-diphenylphosphine 

Downstream Products

• 1190882-84-8 2-fluoro-3-hydroxy-1,3-diphenyl-1(E)-propenyl diphenyl phosphine oxide 

Relevant academic research and scientific papers

Solvent-free Zn(OTf)2-catalyzed dehydrative cross coupling of propargyl alcohols with diarylphosphine oxides to afford allenylphosphine oxides

A less expensive and more environmentally friendly Zn(OTf)2-catalyzed dehydrative coupling reaction of propargyl alcohols with diarylphosphine oxides is reported. The reaction takes place under mild and solvent free conditions, and features a h

Cadmium(II) Chloride-Catalyzed Dehydrative C?P Coupling of Propargyl Alcohols with Diarylphosphine Oxides to Afford Allenylphosphine Oxides

The cadmium(II) chloride-catalyzed dehydrative C?P cross-coupling reaction of propargyl alcohols with diarylphosphine oxides is reported. Several propargyl alcohols including those bearing the sterically demanding tert-butyl group at the triple bond terminus can be used as good substrates in the reaction to produce the corresponding allenylphosphine oxides in good to high yields in acetonitrile at 100 °C. The reaction can also be easily scaled up to a gram-scale synthesis. A mechanism study indicates that the reaction may proceed through a process of propargylic substitution to generate phosphonite intermediates followed by [2,3] sigmatropic rearrangement to produce the allenyl products, rather than through a common allenylative substitution resulting from P-nucleophilicity. (Figure presented.).

Copper-Catalyzed Direct Coupling of Unprotected Propargylic Alcohols with P(O)H Compounds: Access to Allenylphosphoryl Compounds under Ligand- and Base-Free Conditions

The first facile and efficient copper-catalyzed direct C-P cross-coupling of unprotected propargylic alcohols with P(O)H compounds has been developed, providing a general, one-step approach to construct valuable allenylphosphoryl frameworks with operational simplicity and high step- and atom-economy under ligand-, base-, and additive-free conditions.

Spontaneous resolution upon crystallization of allenyl-bis-phosphine oxides

The first example of 'spontaneous resolution by crystallization' in allene chemistry, by means of crystal structures and solid state CD spectra of the R and S enantiomers, is presented. These allenes are prepared by the simple reaction of Ph2PC

Modular synthesis of Ar-BINMOL-phos for catalytic asymmetric alkynylation of aromatic aldehydes with unexpected reversal of enantioselectivity

An interesting group of multifunctional phosphines (Ar-BINMOL-Phos; Ar-BINMOL=1,1-binaphthalene-2-α-arylmethanol-2-ol) with multi-stereogenic centers of axial and sp3-central chirality has been prepared successfully from a single chiral source through a concise synthetic route, in which the neighbouring lithium-promoted [1,2]-Wittig rearrangement proceeding with excellent diastereoselectivity and enantioselectivity is the key process in this approach. Also, in the catalytic alkynylation of aromatic aldehydes with terminal alkynes, the combination of these Ar-BINMOL-Phos ligands with dimethylzinc was found to be an effective catalyst system to afford predominantly the S-configured propargylic alcohols, whereas the additional use of calcium hydride and n-butyllithium along with the same Ar-BINMOL-Phos ligands gave the R-configured products in high yields and excellent enantioselectivities (up to >99% ee).

Studies on highly regio- and stereoselective fluorohydroxylation reaction of 3-aryl-1,2-allenyl phosphine oxides with Selectfluor

The fluorohydroxylation of allenyl phosphine oxides with Selectfluor in commercial MeCN without prior treatment or a mixed solvent of anhydrous MeCN (refluxed over CaH2 and distilled before use) and 7.0 equiv of H2O or MeNO2/su