A study on the regio- and stereoselectivity in palladium-catalyzed cyclizations of alkenes and alkynes bearing bromoaryl and nucleophilic groups

被引：30
|
作者：
Bruyère, D [1 ]
Bouyssi, D [1 ]
Balme, G [1 ]
机构：
[1] Univ Lyon 1, CNRS, UMR 5181, Lab Chim Organ 1,CPE, F-69622 Villeurbanne, France
来源：
TETRAHEDRON | 2004年 / 60卷 / 18期
关键词：
stereoselectivity; biscyclization; palladium;
D O I：
10.1016/j.tet.2004.03.023
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We have studied the remarkable dependence of the stereochemistry of the cyclization on the double bond geometry and of the effect of the bulkiness of the nucleophile on the regiochemistry of the palladium mediated cyclization of alkenes bearing aryl bromides and nucleophiles. In contrast. the cyclization of the acetylenic homologous substrates is not dependent on the nature of the nucleophile. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4007 / 4017
页数：11
相关论文
共 50 条
  • [1] Palladium-Catalyzed Regio- and Stereoselective Chlorothiolation of Terminal Alkynes with Sulfenyl Chlorides
    Iwasaki, Masayuki
    Fujii, Tomoya
    Yamamoto, Arisa
    Nakajima, Kiyohiko
    Nishihara, Yasushi
    CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (01) : 58 - 62
  • [2] Palladium-Catalyzed Regio- and Stereoselective Hydrosilylation of Electron-Deficient Alkynes
    Sumida, Yuto
    Kato, Tomoe
    Yoshida, Suguru
    Hosoya, Takamitsu
    ORGANIC LETTERS, 2012, 14 (06) : 1552 - 1555
  • [3] Palladium-Catalyzed Regio- and Stereoselective Carbothiolation of Terminal Alkynes with Azolyl Sulfides
    Iwasaki, Masayuki
    Topolovcan, Nikola
    Hu, Hao
    Nishimura, Yugo
    Gagnot, Glwadys
    Nakorn, Rungsaeng Na
    Yuvacharaskul, Ramida
    Nakajima, Kiyohiko
    Nishihara, Yasushi
    ORGANIC LETTERS, 2016, 18 (07) : 1642 - 1645
  • [4] Origin of the regio- and stereoselectivity in palladium-catalyzed electrophilic substitution via bis(allyl)palladium complexes
    Wallner, OA
    Szabó, KJ
    CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (17) : 4025 - 4030
  • [5] Regio- and Stereoselective Synthesis of Benzo--sultams by Palladium-Catalyzed Hydrocarbonation of Alkynes
    Debnath, Sudarshan
    Mondal, Shovan
    SYNTHESIS-STUTTGART, 2016, 48 (05): : 710 - 722
  • [6] Palladium-Catalyzed Hydroformylation of Alkenes and Alkynes
    Zhang, Yang
    Sigrist, Michel
    Dydio, Pawel
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (44) : 5985 - 5997
  • [7] Palladium-catalyzed hydrophosphinylation of alkenes and alkynes
    Deprèle, S
    Montchamp, JL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (32) : 9386 - 9387
  • [8] Regio- and stereoselectivity control in palladium-catalyzed allylic alkylation of 1-cycloalkenylmethyl acetates
    Jacquet, Olivier
    Legros, Jean-Yves
    Coliboeuf, Matthieu
    Fiaud, Jean-Claude
    TETRAHEDRON, 2008, 64 (27) : 6530 - 6536
  • [9] Achieving Chemo-, Regio-, and Stereoselectivity in Palladium-Catalyzed Reaction of γ-Borylated Allylic Acetates
    Kukkadapu, Krishna Kishore
    Ouach, Aziz
    Lozano, Pedro
    Vaultier, Michel
    Pucheault, Mathieu
    ORGANIC LETTERS, 2011, 13 (15) : 4132 - 4135
  • [10] A steric control of regioselectivity in palladium-catalyzed cyclizations of alkenes bearing arylbromides and nucleophiles
    Bruyere, D
    Gaignard, G
    Bouyssi, D
    Balme, G
    Lancelin, JM
    TETRAHEDRON LETTERS, 1997, 38 (05) : 827 - 830
12345