Palladium-Catalyzed Tandem Cycloisomerization/Cross-Coupling of Carbonyl- and Imine-Tethered Alkylidenecyclopropanes

被引:11
|
作者
Verdugo, Felipe [1 ,2 ]
Rodino, Ricardo [1 ,2 ]
Calvelo, Martin [1 ,2 ]
Mascarenas, Jose Luis [1 ,2 ]
Lopez, Fernando [1 ,2 ,3 ]
机构
[1] Univ Santiago de Compostela, Ctr Singular Invest Quim Biol & Mat Mol CIQUS, Santiago De Compostela, Spain
[2] Univ Santiago de Compostela, Dept Quim Organ, Santiago De Compostela, Spain
[3] CSIC, Mision Biol Galicia MBG, Pontevedra 36680, Spain
关键词
Alkylidenecyclopropanes; Boronic Acids; Cycloisomerization; Palladium Catalysis; Tandem Reaction; 3+2 INTRAMOLECULAR CYCLOADDITION; ETHYL CYCLOPROPYLIDENEACETATE; ALKYNES; ALK-5-YNYLIDENECYCLOPROPANES; ALKENYLIDENECYCLOPROPANES; ALKYNYLIDENECYCLOPROPANES; CARBOCYCLIZATION; TRANSFORMATIONS; TRANSMETALATION; COCYCLIZATION;
D O I
10.1002/anie.202202295
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Pd-0 catalysts featuring phosphorus-based monodentate ligands can detour the reactivity of carbonyl-tethered alkylidenecyclopropanes (ACPs) from standard (3+2) cycloadditions towards tandem cycloisomerization/cross-coupling processes. This new reactivity lies on the formation of key pi-allyl oxapalladacyclic intermediates, which are subsequently trapped with external nucleophilic partners, instead of undergoing canonical C-O reductive eliminations. Importantly, the use of imine-tethered ACP's is also feasible. Therefore, the method provides a straightforward and stereoselective entry to a wide variety of highly functionalized cyclic alcohols and amines.
引用
收藏
页数:7
相关论文
共 50 条
  • [21] Palladium-catalyzed cross-coupling reactions of aryl mesylates
    So, Chau Ming
    Kwong, Fuk Yee
    CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 4963 - 4972
  • [22] Palladium-catalyzed Suzuki cross-coupling reactions in a microemulsion
    Vashchenko, Valery
    Krivoshey, Alexander
    Knyazeva, Irina
    Petrenko, Alexey
    Goodby, John W.
    TETRAHEDRON LETTERS, 2008, 49 (09) : 1445 - 1449
  • [23] Palladium-Catalyzed Substitution and Cross-Coupling of Benzylic Fluorides
    Blessley, George
    Holden, Patrick
    Walker, Matthew
    Brown, John M.
    Gouverneur, Veronique
    ORGANIC LETTERS, 2012, 14 (11) : 2754 - 2757
  • [24] PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF HALOAZOLES WITH PHENYLSULFONYLACETONITRILE
    SAKAMOTO, T
    KONDO, Y
    SUGINOME, T
    OHBA, S
    YAMANAKA, H
    SYNTHESIS-STUTTGART, 1992, (06): : 552 - 554
  • [25] SYNTHESIS OF CLOMID USING PALLADIUM-CATALYZED CROSS-COUPLING
    ALHASSAN, MI
    SYNTHETIC COMMUNICATIONS, 1987, 17 (15) : 1787 - 1796
  • [26] Palladium-Catalyzed Cross-Coupling of Polyfluoroarenes with Simple Arenes
    Li, Hu
    Liu, Jia
    Sun, Chang-Liang
    Li, Bi-Jie
    Shi, Zhang-Jie
    ORGANIC LETTERS, 2011, 13 (02) : 276 - 279
  • [27] Palladium-Catalyzed Multialkynyl Cross-Coupling Reactions with Tetraalkynylindates
    Kang, Dongjin
    Eom, Dahan
    Kim, Hyunseok
    Lee, Phil Ho
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (12) : 2330 - 2336
  • [28] Palladium-catalyzed cross-coupling of organolead compounds with organostannanes
    Kang, SK
    Ryu, HC
    Choi, SC
    CHEMICAL COMMUNICATIONS, 1998, (12) : 1317 - 1318
  • [29] Palladium-catalyzed cross-coupling reactions in total synthesis
    Nicolaou, KC
    Bulger, PG
    Sarlah, D
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (29) : 4442 - 4489
  • [30] SYNTHESIS OF BROPARESTROL USING PALLADIUM-CATALYZED CROSS-COUPLING
    ALHASSAN, MI
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 321 (01) : 119 - 121