Suzuki-Miyaura cross-coupling of alkenyl tosylates with alkenyl MIDA boronates

被引：18
|
作者：
Luethy, Monique [1 ]
Taylor, Richard J. K. [1 ]
机构：
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
来源：
TETRAHEDRON LETTERS | 2012年 / 53卷 / 27期
基金：
瑞士国家科学基金会; 英国工程与自然科学研究理事会;
关键词：
Suzuki-Miyaura coupling; Alkenyl tosylates; Alkenyl MIDA boronates; Trans-bromo(N-succinimidyl-bis(triphenylphosphine)Ipalladium(II); PALLADIUM CATALYST; ARYLBORONIC ACIDS; GENERAL-SOLUTION; ARYL TOSYLATES; BORONIC ACIDS; MESYLATES; VINYL; REACTIVITY; SULFONATE; PARTNERS;
D O I：
10.1016/j.tetlet.2012.04.091
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A practical procedure for the palladium-catalysed Suzuki-Miyaura coupling of various alkenyl tosylates with alkenyl MIDA boronates has been developed. Commercially available trans-bromo[N-succinimidyl-bis(triphenylphosphine)Ipalladium(II) [Pd(PPh3)(2)NBS] is an effective catalyst under the slow release conditions of MIDA boronates; with less activated alkenyl tosylates addition of the cheap, air-stable tricyclohexylphosphine tetrafluoroborate enhances reactivity. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3444 / 3447
页数：4
相关论文
共 50 条
  • [31] Decarbonylative Suzuki-Miyaura Cross-Coupling of Aroyl Chlorides
    Zhou, Tongliang
    Xie, Pei-Pei
    Ji, Chong-Lei
    Hong, Xin
    Szostak, Michal
    ORGANIC LETTERS, 2020, 22 (16) : 6434 - 6440
  • [32] Suzuki-Miyaura Cross-Coupling Reactions of Unprotected Haloimidazoles
    Tan, Jiajing
    Chen, Yonggang
    Li, Hongmei
    Yasuda, Nobuyoshi
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (18): : 8871 - 8876
  • [33] An Efficient and Reliable Catalyst System Using Hemilabile Aphos for B-Alkyl Suzuki-Miyaura Cross-Coupling Reaction with Alkenyl Halides
    Ye, Ning
    Dai, Wei-Min
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (05) : 831 - 835
  • [34] Suzuki-Miyaura Coupling of Aryl Nosylates with Diethanolamine Boronates
    Kohler, Philipp
    Perrin, Timothe
    Schafer, Gabriel
    SYNLETT, 2023, 34 (18) : A190 - A191
  • [35] Suzuki-Miyaura Coupling of Aryl Nosylates with Diethanolamine Boronates
    Kohler, Philipp
    Perrin, Timothe
    Schafer, Gabriel
    SYNTHESIS-STUTTGART, 2023, 55 (21): : A190 - A191
  • [36] Microwave-assisted Suzuki-Miyaura cross-coupling of 2-alkyl and 2-alkenyl-benzo-1,3,2-diazaborolanes
    Hadebe, Siphamandla W.
    Sithebe, Siphamandla
    Robinson, Ross S.
    TETRAHEDRON, 2011, 67 (23) : 4277 - 4282
  • [37] Suzuki-Miyaura cross-coupling reaction of aryl and heteroaryl pinacol boronates for the synthesis of 2-substituted pyrimidines
    Asano, Shigehiro
    Kamioka, Seiji
    Isobe, Yoshiaki
    TETRAHEDRON, 2012, 68 (01) : 272 - 279
  • [38] Rh(I)-catalyzed cross-coupling reactions of alkenyl tosylates with potassium aryltrifluoroborates
    Wu, Jie
    Zhang, Liang
    Luo, Yong
    TETRAHEDRON LETTERS, 2006, 47 (38) : 6747 - 6750
  • [39] Research Progress of Suzuki-Miyaura Cross-Coupling Reaction Mechanism
    Zhang, Lei
    Yang, Chen
    Guo, Xuefeng
    Mo, Fanyang
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (09) : 3492 - 3510
  • [40] Scope of the Suzuki-Miyaura Cross-Coupling Reaction of Potassium Trifluoroboratoketohomoenolates
    Molander, Gary A.
    Jean-Gerard, Ludivine
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (03): : 1297 - 1303
12345