Iron-Promoted C-C Bond Formation in the Gas Phase

被引:9
|
作者
Troiani, Anna [1 ]
Rosi, Marzio [2 ,3 ]
Garzoli, Stefania [1 ]
Salvitti, Chiara [1 ]
de Petris, Giulia [1 ]
机构
[1] Univ Roma La Sapienza, Dipartimento Chim & Tecnol Farmaco, I-00185 Rome, Italy
[2] Univ Perugia, Dipartimento Ingn Civile & Ambientale, I-06125 Perugia, Italy
[3] ISTM CNR, I-06125 Perugia, Italy
关键词
carbon-carbon coupling; gas-phase chemistry; ion-molecule reactions; iron; reaction mechanisms; ION-CYCLOTRON RESONANCE; COORDINATION CHEMISTRY; ELECTRON CORRELATION; SEQUENTIAL LIGATION; RADICAL CATIONS; ACTIVATION; FERROCENE; (C-C5H5)FE+; LIGANDS; STATE;
D O I
10.1002/anie.201506932
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An unusual iron transfer and carbon-carbon coupling take place in gas-phase ionized mixtures containing ferrocene and dichloromethane. Ferrous chloride and the protonated benzenium ion are eventually formed by a thermal and efficient reaction, through stable intermediates that undergo a remarkable reorganization. The mechanism of the concerted iron extrusion, carbon-chlorine bond activation and carbon-carbon bond formation is elucidated by electronic structure calculations that show the crucial role of iron.
引用
收藏
页码:14359 / 14362
页数:4
相关论文
共 50 条
  • [31] IRON CARBONYL-CATALYZED REACTIONS OF C-C BOND FORMATION WITH HIGH DE
    GASANOV, R
    ILYINSKAYA, LV
    BELOKON, YN
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 78 - ORGN
  • [32] Catalytic C-C bond formation promoted by Mg-Al-O-t-Bu hydrotalcite
    Choudary, BM
    Kantam, ML
    Kavita, B
    Reddy, CV
    Figueras, F
    TETRAHEDRON, 2000, 56 (47) : 9357 - 9364
  • [33] Efficient C-C Bond Formation and Cleavage Reaction Promoted by Triethylborane and Late Transition Metal Catalysis
    Kimura, Masanari
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2012, 70 (03) : 216 - 226
  • [34] Iron-Catalyzed π-Activated C-O Ether Bond Cleavage with C-C and C-H Bond Formation
    Fan, Xiaohui
    Cui, Xiao-Meng
    Guan, Yong-Hong
    Fu, Lin-An
    Lv, Hao
    Guo, Kun
    Zhu, Hong-Bo
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (03) : 498 - 501
  • [35] Decarboxylative C-C and C-N Bond Formation by Ligand-Accelerated Iron Photocatalysis
    Feng, Guangshou
    Wang, Xiaofei
    Jin, Jian
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (39) : 6728 - 6732
  • [36] A Selective C-C Bond Cleavage Strategy Promoted by Visible Light
    Gallo, Rafael D. C.
    Duarte, Marcelo
    da Silva, Amanda F.
    Okada, Celso Y., Jr.
    Deflon, Victor M.
    Jurberg, Igor D.
    ORGANIC LETTERS, 2021, 23 (22) : 8916 - 8920
  • [37] Merging base-promoted C-C bond cleavage and iron-catalyzed skeletal rearrangement involving C-C/C-H bond activation: synthesis of highly functionalized carbazoles
    Kong, Lingkai
    Wang, Mengdan
    Wang, Ye
    Song, Bo
    Yang, Yajie
    Yao, Qiyi
    Li, Yanzhong
    CHEMICAL COMMUNICATIONS, 2018, 54 (78) : 11009 - 11012
  • [38] Lewis acid promoted C-C and copper-catalyzed C-O bond formation: synthesis of neoflavans
    Suchand, B.
    Krishna, J.
    Mritunjoy, K.
    Satyanarayana, G.
    RSC ADVANCES, 2014, 4 (27): : 13941 - 13945
  • [39] New methods for enantioselective C-C bond formation
    Corey, EJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U359 - U359
  • [40] ZR MEDIATED C-C BOND FORMATION CHEMISTRY
    JORDAN, RF
    GUO, ZY
    GURAM, AS
    RODEWALD, S
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 205 : 38 - INOR