Harnessing C-O Bonds in Stereoselective Cross-Coupling and Cross-Electrophile Coupling Reactions

被引:7
|
作者
Jarvo, Elizabeth R. [1 ]
Sanford, Amberly B. [1 ]
机构
[1] Univ Calif Irvine, Dept Chem, Nat Sci 2, Irvine, CA 92697 USA
关键词
nickel catalysis; cross-coupling; cross-electrophile coupling; asymmetric synthesis; enantioselective synthesis; ENANTIOSPECIFIC TOTAL-SYNTHESIS; ENANTIOSELECTIVE ADDITION; GRIGNARD-REAGENTS; NICKEL; ALDEHYDES; (-)-PUNCTATIN-A; MOLECULES; ALCOHOLS; ESTERS;
D O I
10.1055/s-0040-1705987
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We discuss our laboratory's research in the activation of alcohol derivatives in cross-coupling and cross-electrophile coupling reactions. Our developed methods enable the use of secondary alcohols to afford tertiary stereogenic centers, which we applied to the synthesis of pharmaceutically relevant compounds and substructures. We first-discuss the synthesis of bioactive compounds through stereospecific Kumada cross-coupling reactions and follow this with a discussion on the development of our stereoselective cross-electrophile coupling-reaction to synthesize cyclopropanes.
引用
收藏
页码:1151 / 1156
页数:6
相关论文
共 50 条
  • [31] Nickel-catalyzed stereospecific reductive cross-electrophile coupling reactions
    Jarvo, Elizabeth
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [32] Chromium-Catalyzed Selective Cross-Electrophile Coupling between Unactivated C(aryl)-F and C(aryl)-O Bonds
    Fan, Fei
    Zhao, Lixing
    Luo, Meiming
    Zeng, Xiaoming
    ORGANOMETALLICS, 2022, 41 (05) : 561 - 568
  • [33] Beyond C-H and C-O activation: the evolution of components in cross-coupling reactions
    Chen, Kang
    Zhang, Xi-Sha
    Shi, Zhang-Jie
    PURE AND APPLIED CHEMISTRY, 2014, 86 (03) : 361 - 372
  • [34] Phosphorus ligand-coupling for cross-electrophile coupling of pyridines and diazines
    Boyle, Benjamin
    Hilton, Michael
    McNally, Andrew
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [35] Chromium(II)-Catalyzed Stereoselective Cross-Electrophile Coupling of Geminal Difluoroalkenes with Aliphatic Halides
    Hou, Yunqian
    Zeng, Xiaoming
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2025,
  • [36] Cross-Electrophile Coupling of Vinyl Halides with Alkyl Halides
    Johnson, Keywan A.
    Biswas, Soumik
    Weix, Daniel J.
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (22) : 7399 - 7402
  • [37] Cross-Electrophile Coupling: Principles, Methods, and Applications in Synthesis
    Ehehalt, Lauren E.
    Beleh, Omar M.
    Priest, Isabella C.
    Mouat, Julianna M.
    Olszewski, Alyssa K.
    Ahern, Benjamin N.
    Cruz, Alexandro R.
    Chi, Benjamin K.
    Castro, Anthony J.
    Kang, Kai
    Wang, Jiang
    Weix, Daniel J.
    CHEMICAL REVIEWS, 2024,
  • [38] Enantioselective Ni-catalyzed cross-electrophile coupling
    Reisman, Sarah
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [39] Electrochemically driven cross-electrophile coupling of alkyl halides
    Wen Zhang
    Lingxiang Lu
    Wendy Zhang
    Yi Wang
    Skyler D. Ware
    Jose Mondragon
    Jonas Rein
    Neil Strotman
    Dan Lehnherr
    Kimberly A. See
    Song Lin
    Nature, 2022, 604 : 292 - 297
  • [40] Synthesis of α-Vinyltrialkoxysilanes via Nickel-Mediated Cross-Electrophile Coupling Reactions
    Chindan, Bincy
    Syam, Anagha
    Mahendran, Hariharan
    Rasappan, Ramesh
    ORGANIC LETTERS, 2023, 25 (42) : 7751 - 7756