Pd-Catalyzed Heck-Type Reaction: Synthesizing Highly Diastereoselective and Multiple Aryl-Substituted P-Ligands

被引:17
作者
Li, Chong [1 ]
Qiang, Xiao-Yue [1 ]
Qi, Zhi-Chao [1 ]
Cao, Bin [1 ]
Li, Jing-Yu [1 ]
Yang, Shang-Dong [1 ,2 ]
机构
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
[2] South China Univ Technol, Key Lab Funct Mol Engn Guangdong Prov, Guangzhou 510640, Guangdong, Peoples R China
关键词
C-H ARYLATION; ASYMMETRIC ARYLATION; PALLADIUM(II) CATALYSIS; KINETIC RESOLUTION; BOND ACTIVATION; MODULAR ACCESS; EFFICIENT; 2,3-DIHYDROFURAN; CONSTRUCTION; SELECTIVITY;
D O I
10.1021/acs.orglett.9b02697
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this work, an efficient palladium-catalyzed Heck-type reaction was successfully used to synthesize a wide range of monoaryl- or diaryl-substituted P-ligands with excellent yields and diastereoselectivity (up to 98% yield, dr >20:1). The preliminary mechanistic studies demonstrated that it possibly underwent a cationic Heck reaction that was assisted by silver salt, and it revealed the significant role of P(O)Ar-2 for excellent yields and diastereoselectivity.
引用
收藏
页码:7138 / 7142
页数:5
相关论文
共 59 条
  • [1] Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153j, 10.1021/cr300153J]
  • [2] Synthesis of tetra-ortho-substituted, phosphorus-containing and carbonyl-containing biaryls utilizing a diels-alder approach
    Ashburn, Bradley O.
    Carter, Rich G.
    Zakharov, Lev N.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (29) : 9109 - 9116
  • [3] The heck reaction as a sharpening stone of palladium catalysis
    Beletskaya, IP
    Cheprakov, AV
    [J]. CHEMICAL REVIEWS, 2000, 100 (08) : 3009 - 3066
  • [4] Bräse S, 1999, ANGEW CHEM INT EDIT, V38, P1071, DOI 10.1002/(SICI)1521-3773(19990419)38:8<1071::AID-ANIE1071>3.0.CO
  • [5] 2-9
  • [6] Brase S., 2004, Metal-Catalyzed Cross-Couplings, V1, P217
  • [7] RECENT DEVELOPMENTS AND NEW PERSPECTIVES IN THE HECK REACTION
    CABRI, W
    CANDIANI, I
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (01) : 2 - 7
  • [8] Dynamic Kinetic Asymmetric Heck Reaction for the Simultaneous Generation of Central and Axial Chirality
    Carmona, Jose A.
    Hornillos, Valentin
    Ramirez-Lopez, Pedro
    Ros, Abel
    Iglesias-Siguenza, Javier
    Gomez-Bengoa, Enrique
    Fernandez, Rosario
    Lassaletta, Jose M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (35) : 11067 - 11075
  • [9] Ligand-Enabled β-C-H Arylation of α-Amino Acids Using a Simple and Practical Auxiliary
    Chen, Gang
    Shigenari, Toshihiko
    Jain, Pankaj
    Zhang, Zhipeng
    Jin, Zhong
    He, Jian
    Li, Suhua
    Mapelli, Claudio
    Miller, Michael M.
    Poss, Michael A.
    Scola, Paul M.
    Yeung, Kap-Sun
    Yu, Jin-Quan
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (09) : 3338 - 3351
  • [10] Overcoming the Limitations of γ- and δ-C-H Arylation of Amines through Ligand Development
    Chen, Yan-Qiao
    Wang, Zhen
    Wu, Yongwei
    Wisniewski, Steven R.
    Qiao, Jennifer X.
    Ewing, William R.
    Eastgate, Martin D.
    Yu, Jin-Quan
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (51) : 17884 - 17894