Nickel-catalysed cycloaddition oligomerisation of 1,6-diynes to medium-size cyclic polyenes

被引:0
|
作者
Okabe, Yuhsaku [1 ]
Yamada, Takeshi [1 ]
Okamoto, Sentaro [1 ]
机构
[1] Kanagawa Univ, Dept Mat & Life Chem, 3-27-1 Rokkakubashi,Kanagawa ku, Yokohama, Kanagawa 2218686, Japan
关键词
POLYMERS; CYCLOPOLYMERIZATION; POLYMERIZATION; DIYNES;
D O I
10.1039/d2py01033j
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Nickel complexes having a sterically demanding N,N- or N,N,N-type ligand are demonstrated to catalyse the cycloaddition oligomerisation of 1,6-heptadiynes to produce medium-size cyclic polyenes selectively with narrow molecular dispersity and minimum side reactions. The resulting cyclic polyenes exhibit non-conjugated behaviour on NMR and UV-Vis. absorption analyses. Meanwhile, regio-isomerised cyclic polyenes including trans-disubstituted alkenes, which are generated via thermal isomerisation of the cyclic polyenes at 200 degrees C, exhibit conjugated behaviour. The present oligomerisation reaction has wide functional group compatibility, enabling the production of medium-size cyclic polyenes bearing various functional groups. A plausible reaction mechanism that accounts for the narrow polydispersity is proposed.
引用
收藏
页码:6126 / 6133
页数:8
相关论文
共 41 条
  • [31] Flexible Synthesis of Fused Benzofuran Derivatives by Rhodium-Catalyzed [2+2+2] Cycloaddition with Phenol-Linked 1,6-Diynes
    Komine, Yoshiyuki
    Kamisawa, Akiyoshi
    Tanaka, Ken
    ORGANIC LETTERS, 2009, 11 (11) : 2361 - 2364
  • [32] Synthesis of 2-haloalkylpyridines via Cp*RuCl-catalyzed cycloaddition of 1,6-diynes with α-halonitriles.: Unusual halide effect in catalytic cyclocotrimerization
    Yamamoto, Y
    Kinpara, K
    Nishiyama, H
    Itoh, K
    ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (15) : 1913 - 1916
  • [33] Concise synthesis of succinimide-fused 1,3-cyclohexadienes via Co-catalyzed [2+2+2] cycloaddition of 1,6-diynes and maleimides
    Cen, Kaili
    Zhai, Ziyi
    Liu, Yuan
    Wei, Jiahao
    Ouyang, Mixia
    He, Guojun
    Huang, Shuyu
    Zhao, Feng
    Cai, Jinhui
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (11): : 3257 - 3262
  • [34] Transition metal-catalyzed [2+2+2] cycloaddition of nitrogen-linked 1,6-diynes: a straightforward route to fused pyrrolidine systems
    Babazadeh, Mirzaagha
    Soleimani-Amiri, Somayeh
    Vessally, Esmail
    Hosseinian, Akram
    Edjlali, Ladan
    RSC ADVANCES, 2017, 7 (69): : 43716 - 43736
  • [35] Synthesis of cyclic gem-dinitro compounds via radical nitration of 1,6-diynes with Fe(NO3)3•9H2O
    Yi, Xiaofei
    Chen, Kai
    Chen, Wei
    Chen, Wanzhi
    Liu, Miaochang
    Wu, Huayue
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (19) : 4725 - 4728
  • [36] Gold(I)-Catalyzed 1,2-Acyloxy Migration/[3+2] Cycloaddition of 1,6-Diynes with an Ynamide Propargyl Ester Moiety: Highly Efficient Synthesis of Functionalized Cyclopenta[b]indoles
    Liu, Jun
    Chen, Ming
    Zhang, Liangwei
    Liu, Yuanhong
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (03) : 1009 - 1013
  • [37] Ruthenium-catalyzed cycloaddition of 1,6-diynes with isothiocyanates and carbon disulfide: First transition-metal catalyzed [2+2+2] cocyclotrimerization involving C=S double bond
    Yamamoto, Y
    Takagishi, H
    Itoh, K
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (01) : 28 - 29
  • [38] Highly chemo- and regio-selective [2+2+2] cycloaddition of unsymmetrical 1,6-diynes with terminal alkynes catalyzed by Cp*Ru(cod)Cl under mild conditions
    Yamamoto, Y
    Ogawa, R
    Itoh, K
    CHEMICAL COMMUNICATIONS, 2000, (07) : 549 - 550
  • [39] Ring fission of chiral cyclic acetals plus intramolecular [4+2] cycloaddition:: a sequential access to medium-size lactones.: Application to the synthesis of carbasugars
    Lemiègre, L
    Stevens, RL
    Combret, JC
    Maddaluno, J
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (07) : 1308 - 1318
  • [40] New type of transannular reactions in azirine-fused medium-size heterocycles: Selective transformations of azirino[2,1-e][1,6]benzoxazocines and -benzothiazocines into oxa(thia)zine and oxa(thia)zole derivatives
    E. Yu. Shinkevich
    M. S. Novikov
    A. F. Khlebnikov
    R. R. Kostikov
    J. Kopf
    J. Magull
    Russian Journal of Organic Chemistry, 2007, 43 : 1065 - 1079