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配体促进的γ-C(sp3)-H 芳基化和不对称二芳基化反应合成非天然氨基酸衍生物。

Ligand-Promoted γ-C(sp)-H Arylation and Unsymmetrical Diarylation to Access Unnatural Amino Acid Derivatives.

机构信息

Organic and Medicinal Chemistry Division , CSIR-Indian Institute of Chemical Biology 4 Raja S. C. Mullick Road , Jadavpur, Kolkata 700032 , West Bengal , India.

Academy of Scientific and Innovative Research (AcSIR) , Kolkata 700032 , West Bengal , India.

出版信息

Org Lett. 2018 May 4;20(9):2667-2671. doi: 10.1021/acs.orglett.8b00874. Epub 2018 Apr 23.

Abstract

A palladium(II)-catalyzed arylation of a γ-C(sp)-H bond of protected amino acid is explored. The monoarylation is promoted by the commercially available, inexpensive phenanthroline ligand, and toxic silver salt is replaced by earth-abundant Mn(III)acetate. Subsequently, a hitherto unknown unsymmetrical diarylation at the γ-position is accomplished under the modified reaction conditions. Ligands have a prominent influence in both mono- and unsymmetrical diarylations.

摘要

探索了钯(II)催化的保护氨基酸的γ-C(sp)-H 键芳基化反应。单芳基化反应由商业上可获得的、廉价的菲咯啉配体促进,并且有毒的银盐被丰富的锰(III)醋酸盐所取代。随后,在改进的反应条件下,在γ-位上完成了迄今为止未知的不对称二芳基化反应。配体在单芳基化和不对称二芳基化反应中都有显著的影响。

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