1,6-Enyne Cyclizations Catalyzed by N-Heterocyclic Carbene Supported Gold Complexes: Deconvoluting Sterics and Electronics

被引：25
|
作者：
Arumugam, Kuppuswamy [1 ,2 ]
Varghese, Bibin [1 ]
Brantley, Johnathan N. [1 ]
Konda, Sai S. M. [1 ]
Lynch, Vincent M. [1 ]
Bielawski, Christopher W. [1 ]
机构：
[1] Univ Texas Austin, Dept Chem, Austin, TX 78712 USA
[2] St Bonaventure Univ, Dept Chem, St Bonaventure, NY 14778 USA
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 03期
基金：
美国国家科学基金会;
关键词：
N-heterocyclic carbenes; Gold; Isomerization; Enynes; Steric hindrance; INTERMOLECULAR ADDITION; EFFICIENT; PLATINUM; LIGANDS; CYCLOISOMERIZATIONS; HYDROXYCYCLIZATION; ALKOXYCYCLIZATION; HYDROAMINATION; HYDROARYLATION; REARRANGEMENT;
D O I：
10.1002/ejoc.201301137
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of N-heterocyclic carbene (NHC) supported gold(I) complexes were synthesized, characterized in solution as well as in the solid state, and examined as precatalysts for 1,6-enyne cycloisomerization reactions. The product mixtures obtained for a variety of 1,6-enyne isomerizations were governed primarily by the electronic properties of the aforementioned precatalysts. In particular, precatalysts containing electronic-rich NHC ligands showed increased selectivity for bicyclic products, whereas analogous precatalysts supported by electron-deficient NHCs preferentially afforded olefinic products.
引用
收藏
页码：493 / 497
页数：5
相关论文
共 50 条
  • [1] Gold(I)-Catalyzed 1,6-Enyne Single-Cleavage Rearrangements: The Complete Picture
    Garcia-Padilla, Eduardo
    Maseras, Feliu
    Echavarren, Antonio M.
    ACS ORGANIC & INORGANIC AU, 2023, 3 (05): : 312 - 320
  • [2] Axially Chiral N-Heterocyclic Carbene Gold(I) Complex Catalyzed Asymmetric Cycloisomerization of 1,6-Enynes
    Wang, Wenfeng
    Yang, Jinming
    Wang, Feijun
    Shi, Min
    ORGANOMETALLICS, 2011, 30 (14) : 3859 - 3869
  • [3] N-Heterocyclic Carbene Gold Complexes Active in Hydroamination and Hydration of Alkynes
    Mariconda, Annaluisa
    Sirignano, Marco
    Troiano, Rubina
    Russo, Simona
    Longo, Pasquale
    CATALYSTS, 2022, 12 (08)
  • [4] Synthesis and Reactivity of N-Heterocyclic Carbene Gold(I) and Gold(III) Imidate Complexes and Their Catalytic Activity in 1,5-Enyne Cycloisomerization
    Reeds, Jonathan P.
    Whitwood, Adrian C.
    Healy, Mark P.
    Fairlamb, Ian J. S.
    ORGANOMETALLICS, 2013, 32 (10) : 3108 - 3120
  • [5] The Development and Catalytic Uses of N-Heterocyclic Carbene Gold Complexes
    Nolan, Steven P.
    ACCOUNTS OF CHEMICAL RESEARCH, 2011, 44 (02) : 91 - 100
  • [6] Diastereodivergent Hydrosilylative Enyne Cyclization Catalyzed by N-Heterocyclic Carbene-Ni(0)†
    Yu, Meng
    Yong, Xuefeng
    Gao, Weiwei
    Ho, Chun-Yu
    CHINESE JOURNAL OF CHEMISTRY, 2021, 39 (06) : 1587 - 1592
  • [7] Antimicrobial Properties of Some Bis(Iminoacenaphthene (BIAN)-Supported N-Heterocyclic Carbene Complexes of Silver and Gold
    Butorac, Rachel R.
    Al-Deyab, Salem S.
    Cowley, Alan H.
    MOLECULES, 2011, 16 (03) : 2285 - 2292
  • [8] Steric tuning of C2-symmetric chiral N-heterocyclic carbene in gold-catalyzed asymmetric cyclization of 1,6-enynes
    Yamada, Ken-ichi
    Matsumoto, Yasumasa
    Selim, Khalid B.
    Yamamoto, Yasutomo
    Tomioka, Kiyoshi
    TETRAHEDRON, 2012, 68 (22) : 4159 - 4165
  • [9] Synthesis of chiral polycyclic N-heterocycles via gold(i)-catalyzed 1,6-enyne cyclization/intramolecular nucleophilic addition
    Han, Xu
    Gaignard-Gaillard, Quentin
    Retailleau, Pascal
    Gandon, Vincent
    Voituriez, Arnaud
    CHEMICAL COMMUNICATIONS, 2022, 58 (18) : 3043 - 3046
  • [10] Chiral N-Alkylfluorenyl-Substituted N-Heterocyclic Carbenes in the Gold(I)-Catalyzed Enantioselective Cycloisomerization of 1,6-Enynes
    Heinrich, Robin
    Marie-Rose, Giovany
    Gourlaouen, Christophe
    Pale, Patrick
    Brenner, Eric
    Blanc, Aurelien
    CHEMISTRY-A EUROPEAN JOURNAL, 2025, 31 (19)
12345