Copper(II)-Promoted C-C Bond Formation by Oxidative Coupling of Two C(sp3)-H Bonds Adjacent to Carbonyl Group to Construct 1,4-Diketones and Tetrasubstituted Furans

被引：25
作者：
Mao, Shuai [1 ]
Gao, Ya-Ru [1 ]
Zhang, Shao-Liang [1 ]
Guo, Dong-Dong [1 ]
Wang, Yong-Qiang [1 ]
机构：
[1] NW Univ Xian, Key Lab Synthet & Nat Funct Mol Chem, Minist Educ, Dept Chem & Mat Sci, Xian 710069, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 2015卷 / 04期
基金：
中国国家自然科学基金;
关键词：
Synthetic methods; C-C coupling; Oxidation; Copper; Oxygen heterocycles; CATALYZED SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; REGIOSELECTIVE SYNTHESIS; AROMATIC POLYAMIDES; H FUNCTIONALIZATION; TERTIARY-AMINES; BENZYL KETONES; STRATEGY; CYCLIZATION; ALKYNES;
D O I：
10.1002/ejoc.201403274
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The copper(II)-promoted C-C bond formation from the coupling of two C(sp(3))-H bonds that are adjacent to a carbonyl group was achieved. This protocol offers a simple and efficient approach to 2,3-disubstituted 1,4-diketones and tetrasubstituted furans. This method features a wide substrate scope and high functional group tolerance.
引用
收藏
页码：876 / 885
页数：10
相关论文
共 93 条
  • [1] Aerobic Copper-Catalyzed Organic Reactions
    Allen, Scott E.
    Walvoord, Ryan R.
    Padilla-Salinas, Rosaura
    Kozlowski, Marisa C.
    [J]. CHEMICAL REVIEWS, 2013, 113 (08) : 6234 - 6458
  • [2] [Anonymous], 2014, Angew. Chem
  • [3] [Anonymous], 2014, ANGEW CHEM
  • [4] [Anonymous], 2013, ANGEW CHE
  • [5] [Anonymous], 2012, ANGEW CHEM INT EDIT
  • [6] Rhodium-catalyzed synthesis of 2,3-diaryl-1,4-diketones via oxidative coupling of benzyl ketones using α-thioketone oxidizing reagent
    Arisawa, Mieko
    Li, Guangzhe
    Yamaguchi, Masahiko
    [J]. TETRAHEDRON LETTERS, 2013, 54 (10) : 1298 - 1301
  • [7] Baran P.S., 2006, Angew. Chem, V118, P7241, DOI 10.1002/ange.200603024
  • [8] Intermolecular oxidative enolate heterocoupling
    Baran, Phil S.
    DeMartino, Michael P.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (42) : 7083 - 7086
  • [9] Synthesis, anticancer activity, and iron affinity of the Actinoplanes metabolite 7,8-dihydroxy-1-methylnaphtho[2,3-c]furan-4,9-dione
    Breyer, Sandra
    Effenberger-Neidnicht, Katharina
    Knauer, Sebastian
    Schobert, Rainer
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (03) : 1264 - 1267
  • [10] Tandem Suzuki-Miyaura Coupling/Acid-Catalyzed Cyclization between Vinyl Ether Boronates and Vinyl Halides: A Concise Approach to Polysubstituted Furans
    Butkevich, Alexey N.
    Meerpoel, Lieven
    Stansfield, Ian
    Angibaud, Patrick
    Corbu, Andrei
    Cossy, Janine
    [J]. ORGANIC LETTERS, 2013, 15 (15) : 3840 - 3843
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