Enol Silyl Ethers via Copper(II)-Catalyzed C-O Bond Formation

被引:29
|
作者
Chan, Daniel G. [1 ]
Winternheimer, David J. [1 ]
Merlic, Craig A. [1 ]
机构
[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
基金
美国国家科学基金会;
关键词
CROSS-COUPLING REACTIONS; CATALYZED SYNTHESIS; ALIPHATIC-ALCOHOLS; CARBONYL-COMPOUNDS; SYNTHETIC METHODS; TERMINAL ALKYNES; NATURAL-PRODUCTS; CUPRIC ACETATE; DIARYL ETHERS; ALKENYLSILANOLS;
D O I
10.1021/ol2009297
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Copper(II) acetate catalyzes the coupling of pinacol vinylboronates with silanols producing enol silyl ethers. This represents a novel enol silyl ether synthesis via formation of the C-O bond instead of the conventional Si-O bond. This also constitutes the first transition-metal-catalyzed oxidative cross-coupling with silanols.
引用
收藏
页码:2778 / 2781
页数:4
相关论文
共 50 条
  • [31] Copper Catalyzed Synthesis of Heterocyclic Molecules via C-N and C-O Bond Formation under Microwaves: A Mini-Review
    Jena, Sushovan
    Chanda, Kaushik
    ACS OMEGA, 2023, 8 (26): : 23240 - 23256
  • [32] Cobalt-Catalyzed Formation of Grignard Reagents via C-O or C-S Bond Activation
    Pietrasiak, Ewa
    Ha, Seongmin
    Jeon, Seungwon
    Jeong, Jongheon
    Lee, Jiyeon
    Seo, Jongcheol
    Lee, Eunsung
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (13): : 8380 - 8389
  • [33] CARBON CARBON BOND FORMATION BY SELECTIVE COUPLING OF ENOL SILYL ETHERS WITH OXIME SULFONATES
    MATSUMURA, Y
    FUJIWARA, J
    MARUOKA, K
    YAMAMOTO, H
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (20) : 6312 - 6314
  • [34] The C-O Bond, Part III: Ethers By a Knockout
    Smith, Brian C.
    SPECTROSCOPY, 2017, 32 (05) : 22 - 26
  • [35] Hydroaryloxylation of olefins, and C-O bond cleavage via dehydroaryloxylation of ethers, catalyzed by pincer-ligated iridium complexes
    Haibach, Michael C.
    Lease, Nicholas
    Guan, Changjian
    Krogh-Jespersen, Karsten
    Goldman, Alan S.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
  • [36] RHODIUM(I)-CATALYZED ISOMERIZATION OF SILOXYCYCLOPROPANES LEADING TO ENOL SILYL ETHERS AND ALLYL SILYL ETHERS
    IKURA, K
    RYU, I
    OGAWA, A
    TETRAHEDRON LETTERS, 1989, 30 (49) : 6887 - 6890
  • [37] An Attractive and Comprehensive Review on C-O Bond Formation: Nanomagnetic Recoverable Catalysts to Access Diaryl Ethers via C-O Cross-coupling Reactions
    Alwan, Marim
    Hussein, Shaymaa Abed
    Altimari, Usama S.
    Sami, Mustafa Humam
    Dawood, Ashour H.
    Ridha, Benien M.
    Alsalamy, Ali H.
    Kazemi, Mosstafa
    MINI-REVIEWS IN ORGANIC CHEMISTRY, 2025, 22 (04) : 411 - 426
  • [38] Reactions of perfluoroalkanesulfonyl chlorides with silyl enol ethers catalyzed by a ruthenium(II) phosphine complex
    Kamigata, N
    Udodaira, K
    Shimizu, T
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1997, 129 : 155 - 168
  • [39] STEREOSELECTIVE AND REGIOSELECTIVE FORMATION OF SILYL ENOL ETHERS VIA OXIDATION OF VINYL ANIONS
    DAVIS, FA
    LAL, GS
    WEI, J
    TETRAHEDRON LETTERS, 1988, 29 (34) : 4269 - 4272
  • [40] Synthesis of Functionalized Indolines and Dihydrobenzofurans by Iron and Copper Catalyzed Aryl C-N and C-O Bond Formation
    Henry, Martyn C.
    Senn, Hans Martin
    Sutherland, Andrew
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (01): : 346 - 364