54722-13-3Relevant academic research and scientific papers
Chiral Birch reduced tertiary phosphines: Precursors to asymmetric 1,2-cyclohexenebis(tertiary phosphines)
Bulbrook, Michelle,Chu, Minghui,Deane, Karen,Doyle, Roy J.,Hinc, Justina,Peterson, Charlotte,Salem, Geoffrey,Thorman, Nadia,Willis, Anthony C.
supporting information; experimental part, p. 8878 - 8881 (2011/01/06)
The first examples of an optically active Birch reduced tertiary phosphine, viz. (RP)-(cyclohexa-2,5-dienyl)(3-pentyl)phenylphosphine, and successful hydrophosphination of the related racemic ligand (±)- (cyclohexa-2,5-dienyl)(2-propyl)phenylph
Water soluble phosphines Part XV. Syntheses of multiply functionalized and chiral phospine ligands by Pd-catalyzed P-C and C-C coupling reactions
Brauer, David J.,Hingst, Martin,Kottsieper, Konstantin W.,Liek, Christian,Nickel, Thomas,Tepper, Michael,Stelzer, Othmar,Sheldrick, William S.
, p. 14 - 26 (2007/10/03)
Phosphine ligands containing mono- and multiply substituted aromatic substituents (1-13, 19a and 19b) are accessible in high yields by palladium-catalyzed P-C coupling reactions between primary, secondary or disecondary phosphines and iodo- or bromoaromatic compounds. The reaction is of broad applicability and compatible with electron donor or electron acceptor substituents in ortho, meta or para position to the halogen in the aromatic ring systems. It may be performed in protic and aprotic solvents. The chiral spirocyclic boronato complex 15a is formed upon reaction of 3 with boric acid, while with benzeneboronic acid 15c with a peripheral Lewis acid group is obtained. The Pd-mediated P-C coupling reaction of primary phosphines proceeds stepwise, tailor-made chiral secondary (16) and tertiary phosphines (17) being formed in high yield. Through combination with Suzuki-type C-C coupling reactions, the scope of Pd-catalyzed P-C coupling may be extended further, novel ligands (20a, 20b, 21a, 21b) with biphenylyl substituents being accessible. The X-ray structures of the salicylic acid derivative 3 (space group P1) and of ortho-iso-propylphenyl-diphenylphosphine 6 (space group Pbca) have been determined.
SYNTHESIS OF SOME FUNCTIONALIZED PHOSPHINOCARBOXYLIC ACIDS
van Doorn, J. A.,Meijboom, N.
, p. 211 - 222 (2007/10/02)
Various functionalized phosphinocarboxylic acids have been prepared by a number of complementary methods.Reactions of relatively electron-poor secondary phosphides with electron-rich halocarboxylates in liquid ammonia give high yields of phosphinocarboxylates.The substitution reactionmay proceed by a classical SN2 mechanism or by an SN rad mechanism.Reduction of the carboxilate can be a deleterious side reaction in the preparation of phosphinoacetic acids.Several phosphinopropionic acids are prepared by the Michael adition of diphenylphosphine to unsaturated esters.A valuable method proved to be the reaction of dichlorophosphinoacetic ester with functionalized organometallic reagents. Key words: Phosphine; carboxylic acid; ligand; functionalized; synthesis; NMR data.
A Simple Synthesis and Some Synthetic Applications of Substituted Phosphide and Phosphinite Anions
Tsvetkov, E. N.,Bondarenko, N. A.,Malakhova, I. G.,Kabachnik, M. I.
, p. 198 - 208 (2007/10/02)
Based on data for the acidity relationship of phosphines and phosphinous acids and water in dimethyl sulfoxide and water, a simple method is reported for the generation of phosphide and phosphinite anions by the action of concentrated aqueous alkali on primary and secondary phosphines as well as phosphinous acids in dimethyl sulfoxide or other dipolar aprotic solvents.Alkylation of the anion yields secondary and tertiary phosphines, polyphosphines, functionally substituted phosphines as well as similarly substituted phosphine oxides.Phosphinous acids have beenalkylated in various solvents in two-phase systems containing concentrated aqueous alkali and tetrabutylammonium iodide as phase transfer catalyst.
