Synthesis of the new chiral tridentate ligand bis(pyrid-2-ylethyl) menthylphosphine and its use in the palladium-catalyzed allylic alkylations |
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Authors: | Makoto Minato Takefumi Kaneko Shogo Masauji Takashi Ito |
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Institution: | Department of Materials Chemistry, Graduate School of Engineering, Yokohama National University, 79-5 Tokiwadai, Hodogaya-ku, Yokohama 240-8501, Japan |
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Abstract: | We describe the synthesis of a new asymmetric P,N,N′-tridentate ligand (bis(pyrid-2-ylethyl) menthylphosphine, BPEMP), containing two pyridyl rings and (1S,2R,5S)-menthylphosphino group. The ligand is obtained in five steps from natural abundant l-menthol. The coordination behavior of the ligand toward cationic (allylic)Pd(II) moiety and its first application in palladium-catalyzed asymmetric allylic alkylation are presented. Crystallographic and spectroscopic analyses reveal that (η3-allylic)Pd(BPEMP)]+ complex forms only one isomer in the solid state as well as in solution. |
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Keywords: | Palladium Chiral tridentate ligand Allylic alkylation Asymmetric induction |
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