1,4-Diazabicyclo[2.2.2]octane-Promoted Addition Reaction of Tricarbonyl Monohydrates with Active Alkynes via Consecutive C-C/C-O Cleavage

被引:0
作者
Zhang, Jinfeng [1 ]
Ye, Ruyi [1 ]
Li, Ziyang [1 ]
Meng, Lingguo [1 ]
机构
[1] Huaibei Normal Univ, Sch Chem & Mat Sci, Huaibei 235000, Anhui, Peoples R China
关键词
C-C cleavage; C-O cleavage; addition; promoter; BOND-CLEAVAGE; TERMINAL ALKYNOATES; CARBOXYLATE; CYCLIZATION; AZIRIDINES; COMPLEXES; CATALYSIS; ACIDS;
D O I
10.6023/cjoc202104016
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel addition reaction of vicinal tricarbonyl monohydrates with active alkynes proceeded via rapid consecutive C-C/C-O cleavage processes under metal-free and mild reaction conditions, and the transformation was completed within only 1 min. Diverse tricarbonyl monohydrates could react with active alkynes to produce carboxylate esters via these transformations in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO).
引用
收藏
页码:4384 / 4390
页数:7
相关论文
共 46 条
  • [1] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope
    Ackermann, Lutz
    [J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1315 - 1345
  • [2] Regioselective Aliphatic Carbon-Carbon Bond Cleavage by a Model System of Relevance to Iron-Containing Acireductone Dioxygenase
    Allpress, Caleb J.
    Grubel, Katarzyna
    Szajna-Fuller, Ewa
    Arif, Atta M.
    Berreau, Lisa M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (02) : 659 - 668
  • [3] AN IMPROVED METHOD OF NITRATING AROMATIC ORTHO-HYDROXY-CARBOXYLIC ACIDS AND THEIR ESTERS
    BARANY, HC
    PIANKA, M
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1946, (OCT): : 965 - 966
  • [4] Mechanistic Studies of the O2-Dependent Aliphatic Carbon-Carbon Bond Cleavage Reaction of a Nickel Enolate Complex
    Berreau, Lisa M.
    Borowski, Tomasz
    Grubel, Katarzyna
    Allpress, Caleb J.
    Wikstrom, Jeffrey P.
    Germain, Meaghan E.
    Rybak-Akimova, Elena V.
    Tierney, David L.
    [J]. INORGANIC CHEMISTRY, 2011, 50 (03) : 1047 - 1057
  • [5] Serendipitous Synthesis of Pyridoquinazolinones via an Oxidative C-C Bond Cleavage
    Brendel, Matthias
    Sakhare, Priyanka R.
    Dahiya, Gaurav
    Subramanian, Parthasarathi
    Kaliappan, Krishna P.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (12) : 8102 - 8110
  • [6] Ru3(CO)12-catalyzed decarbonylative cleavage of a C-C bond of alkyl phenyl ketones
    Chatani, N
    Ie, Y
    Kakiuchi, F
    Murai, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (37) : 8645 - 8646
  • [7] Intramolecular cyclization of ruthenium vinylidene complexes with a tethering vinyl group: Facile cleavage and reconstruction of the C-C double bond
    Cheng, Cheng-Wei
    Kuo, Yi-Chun
    Chang, Shu-Hao
    Lin, Ying-Chih
    Liu, Yi-Hong
    Wang, Yu
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (48) : 14974 - 14980
  • [8] Copper-Catalyzed N-Benzoylation of Amines via Aerobic C-C Bond Cleavage
    Fan, Wenyou
    Yang, Youqing
    Lei, Jianhua
    Jiang, Qijian
    Zhou, Wang
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (17) : 8782 - 8789
  • [9] FUJI K, 1987, ADV CHEM ACS S SERIE, V215
  • [10] The first example of ring expansion of N-tosylaziridines to 2-aroyl-N-tosylazetidines with nitrogen ylides in an aqueous medium
    Garima
    Srivastava, Vishnu P.
    Yadav, Lal Dhar S.
    [J]. GREEN CHEMISTRY, 2010, 12 (08) : 1460 - 1465