Fourfold Suzuki-Miyaura and Sonogashira Cross-Coupling Reactions on Tetrahedral Methane and Adamantane Derivatives

被引:26
|
作者
Schilling, Christine I. [1 ,2 ]
Plietzsch, Oliver [1 ,2 ]
Nieger, Martin [3 ]
Muller, Thierry [1 ,2 ]
Braese, Stefan [1 ,2 ]
机构
[1] Karlsruhe Inst Technol KIT, Inst Organ Chem, D-76131 Karlsruhe, Germany
[2] Karlsruhe Inst Technol KIT, Ctr Funct Nanostruct CFN, D-76131 Karlsruhe, Germany
[3] Univ Helsinki, Inorgan Chem Lab, FIN-00014 Helsinki, Finland
关键词
Cross-coupling; Hydrocarbons; Adamantane; Organic building unit; Molecular tecton; METAL-ORGANIC FRAMEWORKS; POLYPHENYLENE DENDRIMERS; 1,3,5,7-TETRASUBSTITUTED ADAMANTANES; MOLECULAR TECTONICS; CRYSTAL-STRUCTURES; POLYMER NETWORKS; DIAMONDOID NETS; TETRAPHENYLMETHANE; DESIGN; MORPHOLOGY;
D O I
10.1002/ejoc.201001567
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient way to generate a series of rigid tetrahedral organic building units from common methane and adamantane precursors is presented. Suzuki-Miyaura and Sonogashira cross-coupling reactions are used to effectively generate these shape-persistent molecular tectons. Especially the Sonogashira reactions employing the readily available tetrahedral alkynes and commercial iodides and bromides are very effective.
引用
收藏
页码:1743 / 1754
页数:12
相关论文
共 50 条
  • [1] Suzuki-miyaura cross-coupling reactions of potassium alkenyltrifluoroborates
    Molander, GA
    Bernardi, CR
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (24): : 8424 - 8429
  • [2] Stereospecific and stereoselective Suzuki-Miyaura cross-coupling reactions
    Glasspoole, Ben W.
    Keske, Eric C.
    Crudden, Cathleen M.
    RSC Catalysis Series, 2015, 2015-January (21): : 521 - 550
  • [3] Orbital phase in Suzuki-Miyaura cross-coupling reactions
    Inagaki, Satoshi
    Ikeda, Hirotaka
    TETRAHEDRON LETTERS, 2014, 55 (14) : 2223 - 2225
  • [4] 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
  • [5] Application of hindered ether solvents for palladium catalyzed Suzuki-Miyaura, Sonogashira and cascade Sonogashira cross-coupling reactions
    Sangon, Suwiwat
    Supanchaiyamat, Nontipa
    Sherwood, James
    Macquarrie, Duncan J.
    Noppawan, Pakin
    Hunt, Andrew J.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (12) : 2603 - 2609
  • [6] CuI-catalyzed Suzuki-Miyaura and Sonogashira cross-coupling reactions using DABCO as ligand
    Li, Jin-Heng
    Li, Ji-Lan
    Wang, De-Ping
    Pi, Shao-Feng
    Xie, Ye-Xiang
    Zhang, Man-Bo
    Hu, Xi-Chao
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (06): : 2053 - 2057
  • [7] Suzuki-Miyaura Cross-Coupling of Sulfoxides
    Chen, Qianwei
    Wu, Shufeng
    Yan, Shuqin
    Li, Chengxi
    Abduhulam, Hayrul
    Shi, Yanhui
    Dang, Yanfeng
    Cao, Changsheng
    ACS CATALYSIS, 2020, 10 (15) : 8168 - 8176
  • [8] Suzuki-Miyaura Cross-Coupling of Bromotryptophan Derivatives at Ambient Temperature
    Dachwitz, Steffen
    Duwe, Dario H.
    Wang, Yating Hong
    Gruss, Hendrik
    Hannappel, Yvonne
    Hellweg, Thomas
    Sewald, Norbert
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (69) : 16357 - 16364
  • [9] Reinvestigation of Aminomethyltrifluoroborates and Their Application in Suzuki-Miyaura Cross-Coupling Reactions
    Raushel, Jessica
    Sandrock, Deidre L.
    Josyula, Kanth V.
    Pakyz, Deborah
    Molander, Gary A.
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (08): : 2762 - 2769
  • [10] Recent Progress in the Suzuki-Miyaura Cross-Coupling Reactions in Water
    Xu, Peng
    Duan, Xinhong
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (12) : 3315 - 3327