Hydroalumination of silylacetylenes: a novel and highly stereoselective synthesis of (E)-telluro(silyl)ketene acetals and their applications in Sonogashira cross-coupling reactions

被引：3
作者：
Kawasoko, Cristiane Y. [4 ]
Nazario, Carlos E. D. [4 ]
Santana, Amanda S. [4 ]
Viana, Luiz H. [4 ]
Hurtado, Gabriela R. [4 ]
Marques, Francisco A. [3 ]
Frensch, Gustavo [3 ]
de Oliveira, Paulo R. [2 ]
Guerrero, Palimecio G. [2 ]
Carvalho, Diego B., Jr. [1 ]
Baroni, Adriano C. M. [1 ]
机构：
[1] Univ Fed Mato Grosso do Sul, Dept Farm Bioquim, UFMS, Campo Grande, MS, Brazil
[2] Univ Tecnol Fed Parana, UTFPR, DAQBi, Dept Quim & Biol, Curitiba, Parana, Brazil
[3] Univ Fed Parana UFPR, Dept Quim, Curitiba, Parana, Brazil
[4] Univ Fed Mato Grosso do Sul, UFMS, Dept Quim, Campo Grande, MS, Brazil
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 46期
关键词：
Hydroalumination; (Z)-beta-Vinylorganosilane alanates; Sonogashira cross-coupling; Telluro(silyl)ketene acetals; (Z)-1,4-Diorganyl-2-tri(organyl)silyl-1-buten-3-ynes; IN-SITU FORMATION; DIISOBUTYLALUMINUM HYDRIDE; ORGANOMETALLIC COMPOUNDS; VERSATILE GENERATION; VINYLIC TELLURIDES; TERMINAL ALKYNES; Z-ENYNES; HALIDES; ACETYLENES; HYDRALUMINATION;
D O I：
10.1016/j.tetlet.2011.08.147
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The hydroalumination of silylacetylenes with DIBAL-H followed by the addition of n-butyllithium generated in situ the (Z)-beta-vinylorganosilane alanates intermediates, which were trapped with butyltellurenyl bromide (C4H9TeBr), furnishing exclusively the (E)-1-butyltelluro-1-tri(organyl)silyl-2-organyl-1-alkenes in 45-70% yields. These telluro(silyl)ketene acetals were utilized as substrates in Sonogashira cross-coupling Pd-catalyzed reactions, furnishing the (Z)-1,4-diorganyl-2-tri(organyl)silyl-1-buten-3-ynes with total control of regio- and stereochemistry in 62-80% yield. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6067 / 6071
页数：5
相关论文
共 30 条
  • [21] Highly efficient synthesis of 1,2-disubstituted acetylenes derivatives from the cross-coupling reactions of 1-bromoalkynes with organotitanium reagents
    Wu, Chuan
    Li, Qing-Han
    TETRAHEDRON, 2021, 96
  • [22] Monomeric Three-Coordinate N-Heterocyclic Carbene Nickel(I) Complexes: Synthesis, Structures, and Catalytic Applications in Cross-Coupling Reactions
    Matsubara, Kouki
    Fukahori, Yukino
    Inatomi, Takahiro
    Tazaki, Saeko
    Yamada, Yuji
    Koga, Yuji
    Kanegawa, Shinji
    Nakamura, Toshikazu
    ORGANOMETALLICS, 2016, 35 (19) : 3281 - 3287
  • [23] N-Heterocyclic carbene-Pd(II)-PPh3 complexes as a new highly efficient catalyst system for the Sonogashira cross-coupling reaction: Synthesis, characterization and biological activities
    Boubakri, L.
    Mansour, L.
    Harrath, A. H.
    Ozdemir, I.
    Yasar, S.
    Hamdi, N.
    JOURNAL OF COORDINATION CHEMISTRY, 2018, 71 (02) : 183 - 199
  • [24] Synthesis and applications of polymeric N-heterocyclic carbene palladium complex-grafted silica as a novel recyclable nano-catalyst for Heck and Sonogashira coupling reactions
    Tamami, Bahman
    Farjadian, Fatemeh
    Ghasemi, Soheila
    Allahyari, Hamed
    NEW JOURNAL OF CHEMISTRY, 2013, 37 (07) : 2011 - 2018
  • [25] Microwave-Assisted Synthesis of Novel Perimidinium Salts as N-Heterocyclic Carbene Precursors: Involvement in Palladium-Catalyzed Cross-Coupling Reactions
    Onar, Gulnihan
    Karatas, Mert Olgun
    Alici, Bulent
    Cetinkaya, Engin
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2015, 51 (06) : 563 - 567
  • [26] Highly Efficient Synthesis of 2-Substituted Benzo[b]furan Derivatives from the Cross-Coupling Reactions of 2-Halobenzo[b]furans with Organoalane Reagents
    Wen, Chang
    Wu, Chuan
    Luo, Ruiqiang
    Li, Qinghan
    Chen, Feng
    SYNTHESIS-STUTTGART, 2021, 53 (20): : 3847 - 3861
  • [27] Synthesis and microwave-assisted catalytic activity of novel bis-benzimidazole salts bearing furfuryl and thenyl moieties in Heck and Suzuki cross-coupling reactions
    Yilmaz, Uelkue
    Sireci, Nihat
    Deniz, Selma
    Kucukbay, Hasan
    APPLIED ORGANOMETALLIC CHEMISTRY, 2010, 24 (05) : 414 - 420
  • [28] Synthesis and characterization of functionalized titania-supported Pd catalyst deriving from new orthopalladated complex of benzophenone imine: catalytic activity in the copper-free Sonogashira cross-coupling reactions at low palladium loadings
    Karami, Kazem
    Abedanzadeh, Sedigheh
    Herves, Pablo
    RSC ADVANCES, 2016, 6 (96): : 93660 - 93672
  • [29] Synthesis, characterization, and microwave-promoted catalytic activity of novel benzimidazole salts bearing silicon-containing substituents in Heck-Mizoroki and Suzuki-Miyaura cross-coupling reactions under aerobic conditions
    Kucukbay, Hasan
    Sireci, Nihat
    Yilmaz, Ulku
    Deniz, Selma
    Akkurt, Mehmet
    Baktir, Zeliha
    Buyukgungor, Orhan
    TURKISH JOURNAL OF CHEMISTRY, 2012, 36 (02) : 201 - 217
  • [30] Novel phosphorus-coordinated palladium(II) complexes derived from 3,5-disubstituted-1H-1,2,4-diazaphospholes: Synthesis and catalytic application in Suzuki-Miyaura cross-coupling reactions
    Jia, Xuefeng
    Zhao, Fang
    INORGANICA CHIMICA ACTA, 2017, 461 : 145 - 149
123