The Continuous-Flow Synthesis of Styrenes Using Ethylene in a Palladium-Catalysed Heck Cross-Coupling Reaction

被引：58
|
作者：
Bourne, Samuel L. [1 ]
Koos, Peter [1 ]
O'Brien, Matthew [1 ]
Martin, Benjamin [2 ]
Schenkel, Berthold [2 ]
Baxendale, Ian R. [1 ]
Ley, Steven V. [1 ]
机构：
[1] Univ Cambridge, Dept Chem, Innovat Technol Ctr, Cambridge CB2 1EW, England
[2] Novartis Pharma AG, Chem & Analyt Dev, CH-4057 Basel, Switzerland
来源：
SYNLETT | 2011年 / 18期
基金：
英国工程与自然科学研究理事会;
关键词：
vinylation; membrane; flow; ethylene; styrene; ORGANIC-SYNTHESIS; MICROREACTOR; CHEMISTRY; ARYL; ARYLATION; ECONOMY; HALIDES;
D O I：
10.1055/s-0031-1289291
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report a palladium-catalysed ethylene Heck reaction for the vinylation of aryl iodides using a tube-in-tube gas-liquid reactor. The flow process afforded various styrenes in short reaction times, employing moderate ethylene pressure.
引用
收藏
页码：2643 / 2647
页数：5
相关论文
共 50 条
  • [1] Palladium-catalysed direct cross-coupling of secondary alkyllithium reagents
    Vila, Carlos
    Giannerini, Massimo
    Hornillos, Valentin
    Fananas-Mastral, Martin
    Feringa, Ben L.
    CHEMICAL SCIENCE, 2014, 5 (04) : 1361 - 1367
  • [2] Cross-Coupling Knows No Limits: Assessing the Synthetic Potential of the Palladium-Catalysed Cross-Coupling of Organolithiums
    Firth, James D.
    O'Brien, Peter
    CHEMCATCHEM, 2015, 7 (03) : 395 - 397
  • [3] Palladium-Catalysed Direct Cross-Coupling of Organolithium Reagents with Aryl and Vinyl Triflates
    Vila, Carlos
    Hornillos, Valentin
    Giannerini, Massimo
    Fananas-Mastral, Martin
    Feringa, Ben L.
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (41) : 13078 - 13083
  • [4] Iminophosphine palladium(II) complexes: synthesis, characterization, and application in Heck cross-coupling reaction of aryl bromides
    Yilmaz, Mustafa Kemal
    Guzel, Bilgehan
    APPLIED ORGANOMETALLIC CHEMISTRY, 2014, 28 (07) : 529 - 536
  • [5] A versatile method for the synthesis of diaryl and alkyl aryl ketones via palladium-catalysed cross-coupling reaction of arylboronic acids with acyl chlorides
    Rafiee, Fatemeh
    Hajipour, Abdol R.
    APPLIED ORGANOMETALLIC CHEMISTRY, 2015, 29 (03) : 181 - 184
  • [6] Investigating the mechanism and origins of selectivity in palladium-catalysed carbene insertion cross-coupling reactions
    Lennon, Gavin
    O'Boyle, Christina
    Carrick, Andrew I.
    Dingwall, Paul
    CATALYSIS SCIENCE & TECHNOLOGY, 2023, 13 (02) : 372 - 380
  • [7] Palladium-Catalysed Cross-Coupling of Benzylammonium Salts with Boronic Acids under Mild Conditions
    Turtscher, Paul L.
    Davis, Holly J.
    Phipps, Robert J.
    SYNTHESIS-STUTTGART, 2018, 50 (04): : 793 - 802
  • [8] Zinc-Mediated Regiodiverse Synthesis of Vinyl Bromide Derivatives and Their in situ Palladium-Catalysed Cross-Coupling Reactions
    Miersch, Anne
    Kohlmeyer, Corinna
    Hilt, Gerhard
    SYNTHESIS-STUTTGART, 2013, 45 (23): : 3228 - 3232
  • [9] Synthesis of cinnamyl substituted dihydrofuranones by the Heck cross-coupling reaction
    Ghochikyan, Tariel V.
    Vardanyan, Arpine S.
    Samvelyan, Melanya A.
    Galstyan, Armen S.
    Langer, Peter
    MENDELEEV COMMUNICATIONS, 2020, 30 (02) : 236 - 237
  • [10] Nickel-catalyzed Mizoroki-Heck cross-coupling reaction of aryl halides with styrenes
    Bhange, Dattatraya Soma
    Rasal, Nishant Kisan
    INDIAN JOURNAL OF CHEMISTRY, 2024, 63 (08): : 823 - 829
12345