Metal-Containing Schiff Base/Sulfoxide Ligands for Pd(II)-Catalyzed Asymmetric Allylic C-H Aminations

被引:32
作者
Bunno, Youka [1 ]
Tsukimawashi, Yuta [1 ]
Kojima, Masahiro [1 ]
Yoshino, Tatsuhiko [1 ]
Matsunaga, Shigeki [1 ,2 ]
机构
[1] Hokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
[2] Hokkaido Univ, Global Stn Biosurfaces & Drug Discovery, Sapporo, Hokkaido 0600812, Japan
关键词
asymmetric catalysis; asymmetric synthesis; allylic C-H functionalization; palladium; Schiff base ligand; TERMINAL OLEFINS; OXIDATION; CATALYSIS; COMPLEX; ALLYLATION; ACTIVATION; STRATEGY; ACETATES; ALKENES;
D O I
10.1021/acscatal.0c05261
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Metal-containing Schiff base/sulfoxides were developed as chiral ligands for Pd(II)-catalyzed asymmetric intramolecular allylic C-H amination reactions. The use of metal-containing Schiff base ligands allows tuning the selectivity and reactivity of the Pd(II)-catalyst, whereby a Schiff base-Cu(II)/sulfoxide ligand in combination with Pd(OAc)(2) showed the best performance. Both internal and terminal alkenes were applicable, and the C-H amination products were obtained in up to 91:9 er.
引用
收藏
页码:2663 / 2668
页数:6
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