Asymmetric Pd(II)-Catalyzed C-O, C-N, C-C Bond Formation Using Alkenes as Substrates: Insight into Recent Enantioselective Developments

被引:16
|
作者
Giofre, Sabrina [1 ,2 ]
Molteni, Letizia [3 ]
Beccalli, Egle M. [3 ]
机构
[1] Johannes Gutenberg Univ Mainz, Bioctr, D-55128 Mainz, Germany
[2] Inst Mol Biol, D-55128 Mainz, Germany
[3] Univ Milan, DISFARM, Sez Chim Gen & Organ A Marchesini, I-20133 Milan, Italy
关键词
(aza)-Wacker reaction; Enantioselectivity; Oxidative Heck reaction; Alkenes; Palladium; WACKER-TYPE CYCLIZATION; PALLADIUM-CATALYZED ADDITION; ARYLBORONIC ACIDS; CONJUGATE ADDITION; HECK ARYLATIONS; UNACTIVATED ALKENES; OXIDATIVE CYCLIZATION; OVERMAN REARRANGEMENT; BISOXAZOLINE LIGANDS; CHIRAL LIGAND;
D O I
10.1002/ejoc.202200976
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This Review summarizes the advances in the catalytic enantioselective mono- and difunctionalization of alkenes, highlighting the fundamental role of ligands. Several types of asymmetric reactions have been developed involving different bonds formation, C-O, C-N and C-C, highlighting the urgency to go ahead in the search for new ligands and synthetic methodologies in order to improve the control over the reaction selectivity and activity and thus, to increase the applications in the synthesis of heterocyclic scaffolds and biologically active compounds. The Review is organized into paragraphs, which discuss the type of bond formed during the nucleopalladation, C-O, C-N, C-C bonds, and the type of reaction involved.
引用
收藏
页数:33
相关论文
共 50 条
  • [1] New methods for C-C, C-O, and C-N bond formation
    Walsh, Patrick J.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [2] Radical Capture at Nickel(II) Complexes: C-C, C-N, and C-O Bond Formation
    Bakhoda, Abolghasem Gus
    Wiese, Stefan
    Greene, Christine
    Figula, Bryan C.
    Bertke, Jeffery A.
    Warren, Timothy H.
    ORGANOMETALLICS, 2020, 39 (10) : 1710 - 1718
  • [3] C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents
    Beccalli, Egle M.
    Broggini, Gianluigi
    Martinelli, Michela
    Sottocornola, Silvia
    CHEMICAL REVIEWS, 2007, 107 (11) : 5318 - 5365
  • [4] Zinc-Catalyzed Organic Synthesis: C-C, C-N, C-O Bond Formation Reactions
    Wu, Xiao-Feng
    Neumann, Helfried
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (17) : 3141 - 3160
  • [5] π-Bond Dissociation Energies: C-C, C-N, and C-O
    Kass, Steven R.
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (20): : 15158 - 15163
  • [6] Palladium nanoparticles catalyzed C-C, C-N and C-O bond formation Via C-H activation
    Saha, Rajib
    Sekar, G.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
  • [7] Take the right catalyst:: Palladium-catalyzed C-C, C-N, and C-O bond formation on chloroarenes
    Stürmer, R
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1999, 38 (22) : 3307 - 3308
  • [8] Pd-Catalyzed C-C, C-N, and C-O Bond-Forming Difunctionalization Reactions of Alkenes Bearing Tethered Aryl/Alkenyl Triflates
    White, Derick R.
    Bornowski, Evan C.
    Wolfe, John P.
    ISRAEL JOURNAL OF CHEMISTRY, 2020, 60 (3-4) : 259 - 267
  • [9] Construction of C-C Bond via C-N and C-O Cleavage
    Pang, Xiaobo
    He, Rong-De
    Shu, Xing-Zhong
    SYNLETT, 2020, 31 (07) : 635 - 640
  • [10] Recent developments in the difunctionalization of alkenes with C-N bond formation
    Chen, Xiang
    Xiao, Fang
    He, Wei-Min
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (18) : 5206 - 5228