Synthetic Route of 224311-51-7. Chemistry is an experimental science, and the best way to enjoy it and learn about it is performing experiments.Introducing a new discovery about 224311-51-7, Name is 2-(Di-tert-Butylphosphino)biphenyl
Bicyclic zirconacyclopentenes prepared by the reactions of 1,6- and 1,7-enynes with [Cp2ZrBu2] (Negishi reagent) reacted with a plethora of aldehydes (aryl, heteroaryl, alkyl, alpha,beta-unsaturated) by chemo- and stereoselective insertion into the sp3 C-Zr bond to give the corresponding oxazirconacycloheptenes. Subsequent hydrolysis or halogenolysis provided the corresponding alcohols 4 (31-74% isolated yields) or halides 10 (35-50% isolated yields). The oxazirconacycloheptenes prepared by the insertion of 2-iodobenzaldehyde were also subjected to intramolecular coupling in the presence of CuCl and additives, and compounds possessing the condensed 5-7-6(aryl) ring system were obtained in reasonable isolated yields (32-46%). The same ring system was also prepared by the Pd-catalyzed coupling of dihalo derivatives 10 (38-42% 1H NMR yields). Moreover, the mechanism of the unproductive side-reaction leading to ketones during the reaction with CuCl was elucidated. The insertion of aldehydes into bicyclic zirconacyclopentenes mainly leads to oxazirconacycloheptenes. Subsequent hydrolysis or halogenolysis furnishes the corresponding alcohols or halides in moderate yields. The insertion of o-iodobenzaldehyde followed by intramolecular coupling in the presence of Cu and/or Pd compounds leads to the tricyclic condensed 5-7-6(aryl) ring system in reasonable yields.
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Reference:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate