Recent Advances in Aryne Double Bond Insertion

被引:7
|
作者
Wu, Chunrui [1 ]
Yang, Yupo [2 ]
Shi, Feng [1 ]
机构
[1] Henan Univ, Key Lab Nat Med & lmmunoengn Henan Prov, Kaifeng 475004, Peoples R China
[2] Qingdao Univ Sci & Technol, Coll Chem & Mol Engn, Qingdao 266042, Peoples R China
基金
中国国家自然科学基金;
关键词
aryne; ortho-quinomethide; reactive intermediate; pericyclic reaction; tandem reaction; COUPLING REACTION; STRAIGHTFORWARD SYNTHESIS; VINYLOGOUS AMIDES; O-QUINODIMETHANES; CARBON-CARBON; BENZYNE; CYCLOADDITIONS; BENZOFURANS; CHEMISTRY;
D O I
10.6023/cjoc201411041
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aryne double bond insertion generates an ortho-quinomethide-typed intermediate, which, like aryne itself, is one of the most important reactive intermediates in organic reactions. This review summarizes recent advances in this field and the potential applications in synthetic organic chemistry, with a focus on the reaction mechanism, as well as the structure and reactivity of the ortho-quinomethide intermediates.
引用
收藏
页码:770 / 780
页数:11
相关论文
共 49 条
  • [1] Insertion of Benzynes into the P=N Bond of P-Alkenyl(alkynyl)-λ5-phosphazenes
    Alajarin, Mateo
    Lopez-Leonardo, Carmen
    Raja, Rosalia
    Orenes, Raul-Angel
    [J]. ORGANIC LETTERS, 2011, 13 (20) : 5668 - 5671
  • [2] Reaction of diimines and benzyne
    Aly, AA
    Mohamed, NK
    Hassan, AA
    Mourad, AFE
    [J]. TETRAHEDRON, 1999, 55 (04) : 1111 - 1118
  • [3] Recent advances in transition-metal-free carbon-carbon and carbon-heteroatom bond-forming reactions using arynes
    Bhunia, Anup
    Yetra, Santhivardhana Reddy
    Biju, Akkattu T.
    [J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (08) : 3140 - 3152
  • [4] Insertion of Arynes into Thioureas: A New Amidine Synthesis
    Biswas, Kallolmay
    Greaney, Michael F.
    [J]. ORGANIC LETTERS, 2011, 13 (18) : 4946 - 4949
  • [5] CAUBERE P, 1978, TOP CURR CHEM, V73, P49
  • [6] Chakrabarty S., 2013, ANGEW CHEM INT EDIT, V52, P1
  • [7] Collier SJ, 1998, PROG HET CH, V10, P25, DOI 10.1016/S0959-6380(98)80004-4
  • [8] CYCLOADDITIONS OF BENZYNE WITH CYCLIC OLEFINS - COMPETITION BETWEEN 2 + 4, ENE, AND 2 + 2 REACTION PATHWAYS
    CREWS, P
    BEARD, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (03): : 522 - 528
  • [9] Use of benzynes for the synthesis of heterocycles
    Dubrovskiy, Anton V.
    Markina, Nataliya A.
    Larock, Richard C.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (02) : 191 - 218
  • [10] Enamide-Benzyne-[2+2] Cycloaddition: Stereoselective Tandem [2+2]-Pericyclic Ring-Opening-Intramolecular N-Tethered [4+2] Cycloadditions
    Feltenberger, John B.
    Hayashi, Ryuji
    Tang, Yu
    Babiash, Eric S. C.
    Hsung, Richard P.
    [J]. ORGANIC LETTERS, 2009, 11 (16) : 3666 - 3669