Chiral P,N,N-Ligands for Pd-Catalyzed Asymmetric Allylic Substitutions

被引:0
|
作者
Qin Hao [1 ]
Hou Chuanjin [1 ,2 ]
Liang Dinghua [1 ]
He Xinwei [2 ]
Li Ling [1 ,3 ]
Hu Xiangping [3 ]
机构
[1] Dalian Polytech Univ, Sch Light Ind & Chem Engn, Dalian 116034, Liaoning, Peoples R China
[2] Anhui Normal Univ, Key Lab Funct Mol Solids, Minist Educ, Wuhu 241000, Anhui, Peoples R China
[3] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Liaoning, Peoples R China
关键词
P; N; N-ligands; asymmetric allylic substitution; palladium; FORMAL 3+2 CYCLOADDITION; DECARBOXYLATIVE PROPARGYLIC ALKYLATION; ENANTIOSELECTIVE SYNTHESIS; IRIDIUM CATALYSTS; BETA-KETOESTERS; VICINAL TERTIARY; EFFICIENT ACCESS; HYDROGENATION; ESTERS; DEAROMATIZATION;
D O I
10.6023/cjoc202306004
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral P,N,N-ligands are a new type of ligands developed in recent years, which have been widely used in asymmetric catalytic reactions. In this study, chiral P,N,N-ligands were applied to palladium-catalyzed asymmetric allylic substitution reactions. The results showed that under mild conditions, various nucleophiles containing carbon, nitrogen and oxygen could react smoothly, achieving good yields (up to 97% yield) and enantioselectivities (up to 93% ee).
引用
收藏
页码:282 / 290
页数:9
相关论文
共 50 条
  • [21] Synthesis of chiral P,N-ligands derived from quinoline and their application in asymmetric allylic alkylations
    Shen, Yan-Hong
    Lv, Hui-Chao
    Zhao, Liang
    JOURNAL OF CHEMICAL RESEARCH, 2011, (06) : 349 - 351
  • [22] Novel C2-symmetric planar chiral diphosphine ligands and their application in Pd-catalyzed asymmetric allylic substitutions
    Liu, Delong
    Xie, Fang
    Zhang, Wanbin
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (18): : 6992 - 6997
  • [23] [2.2]paracyclophane-derived chiral P,N-ligands: Design, synthesis, and application in palladium-catalyzed asymmetric allylic alkylation
    Jiang, Biao
    Lei, Yang
    Zhao, Xiao-Long
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (19): : 7833 - 7836
  • [24] Pd-Catalyzed Asymmetric Allylic Etherizations with Oximes by Chiral Alkene-Phosphine Ligands
    Cao, Ziping
    Liu, Zhaoqun
    Liu, Yilin
    Du, Haifeng
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (15): : 6401 - 6406
  • [25] Synthesis of Novel Ferrocenyl-Based P,S Ligands (ThioClickFerrophos) and Their Use in Pd-Catalyzed Asymmetric Allylic Substitutions
    Kato, Minoru
    Nakamura, Tatsuhito
    Ogata, Kenichi
    Fukuzawa, Shin-ichi
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (30) : 5232 - 5238
  • [26] Pd-Catalyzed Asymmetric Allylic Cycloaddition of N-Containing Allylic Carbonates with Isocyanates
    Khan, Ijaz
    Shah, Babar Hussain
    Zhao, Can
    Xu, Feng
    Zhang, Yong Jian
    ORGANIC LETTERS, 2019, 21 (23) : 9452 - 9456
  • [27] Pd-Catalyzed Asymmetric Allylic Alkylations of 3-Substituted Indoles Using Chiral P/Olefin Ligands
    Liu, Yilin
    Du, Haifeng
    ORGANIC LETTERS, 2013, 15 (04) : 740 - 743
  • [28] Origin of enantioselectivity in palladium-catalyzed asymmetric allylic alkylation reactions using chiral N,N-ligands with different rigidity and flexibility
    Drommi, Dario
    Saporita, Maria
    Bruno, Giuseppe
    Faraone, Felice
    Scafato, Patrizia
    Rosini, Carlo
    DALTON TRANSACTIONS, 2007, (15) : 1509 - 1519
  • [29] Asymmetric synthesis of novel ferrocenyl ligands with planar and central chirality and their application to Pd-catalyzed allylic substitutions
    Enders, D
    Peters, R
    Lochtman, R
    Raabe, G
    Runsink, J
    Bats, JW
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2000, 2000 (20) : 3399 - 3426
  • [30] Pd-Catalyzed Asymmetric Allylic Alkylation of Indoles and Pyrroles by Chiral Alkene-Phosphine Ligands
    Cao, Ziping
    Liu, Yilin
    Liu, Zhaoqun
    Feng, Xiangqing
    Zhuang, Minyang
    Du, Haifeng
    ORGANIC LETTERS, 2011, 13 (09) : 2164 - 2167