Electric Literature of 213697-53-1. Let’s face it, organic chemistry can seem difficult to learn. Especially from a beginner’s point of view. Like 213697-53-1, Name is 2′-(Dicyclohexylphosphino)-N,N-dimethyl-[1,1′-biphenyl]-2-amine. In a document type is Article, introducing its new discovery.
We report a general palladium-catalyzed beta-arylation of Boc-piperidines, which yields a variety of valuable 3-arylpiperidines in a simple and direct manner. The beta- vs. alpha-arylation selectivity was controlled by the ligand, with flexible biarylphosphines providing mainly the desired beta-arylated products whereas more rigid biarylphosphines mainly furnished the more classical alpha-arylated products. The computed reaction mechanism (DFT), studied from the common alpha-palladated intermediate, indicated that the reductive elimination steps leading to the alpha- and beta-arylated products are selectivity-determining. Moreover, the experimental trend obtained with different ligands was well reproduced by the calculations.
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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