Direct C-H Carboxylation with Carbon Dioxide Using 1,2,3-Triazol-5-ylidene Copper(I) Complexes

被引:129
|
作者
Inomata, Hiroshi [1 ]
Ogata, Kenichi [1 ]
Fukuzawa, Shin-ichi [1 ]
Hou, Zhaomin [2 ,3 ]
机构
[1] Chuo Univ, Dept Appl Chem, Inst Sci Engn, Bunkyo Ku, Tokyo 1128551, Japan
[2] RIKEN, Adv Sci Inst, Organometall Chem Lab, Wako, Saitama 3510198, Japan
[3] RIKEN, Adv Sci Inst, Adv Catalyst Res Team, Wako, Saitama 3510198, Japan
基金
日本学术振兴会;
关键词
CATALYZED DIRECT CARBOXYLATION; CARBENE LIGANDS; ESTERS; BONDS; TRANSFORMATION; MECHANISM; REAGENTS; DFT; CO2;
D O I
10.1021/ol301760n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1,2,3-Triazol-5-ylidene copper(I) complexes (tzNHC-Cu) efficiently catalyzed the direct C-H carboxylation of benzoxazole and benzothiazole derivatives with CO2 to give the corresponding esters in excellent yields after treatment with alkyl iodide. The tzNHC copper(I) complex, i.e., [(TPr)CuCl], worked somewhat more effectively than the corresponding imidazol-2-ylidene copper(I) complex [(IPr)CuCl] to give the carboxylation product in higher yields.
引用
收藏
页码:3986 / 3989
页数:4
相关论文
共 50 条
  • [21] Ruthenium(II) pincer complexes featuring an anionic CNC bis(1,2,3-triazol-5-ylidene)carbazolide ligand coordinated in a meridional fashion
    Kleinhans, George
    Guisado-Barrios, Gregorio
    Peris, Eduardo
    Bezuidenhout, Daniela I.
    POLYHEDRON, 2018, 143 : 43 - 48
  • [22] Synthesis and Structure of Palladium 1,2,3-Triazol-5-ylidene Mesoionic Carbene PEPPSI Complexes and Their Catalytic Applications in the Mizoroki-Heck Reaction
    Keske, Eric C.
    Zenkina, Olena V.
    Wang, Ruiyao
    Crudden, Cathleen M.
    ORGANOMETALLICS, 2012, 31 (17) : 6215 - 6221
  • [23] Synthesis of Axially Chiral 1,2,3-Triazol-5-ylidene Au(I) Complex and Its Application in Enantioselective [2+2] Cycloaddition of Alleneamides with Alkenes
    Huang, Wei
    Zhang, You-Can
    Jin, Rui
    Chen, Bai-Ling
    Chen, Zili
    ORGANOMETALLICS, 2018, 37 (18) : 3196 - 3209
  • [24] DFT Studies on the Carboxylation of the C-H Bond of Heteroarenes by Copper(I) Complexes
    Ariafard, Alireza
    Zarkoob, Fatemeh
    Batebi, Hossein
    Stranger, Robert
    Yates, Brian F.
    ORGANOMETALLICS, 2011, 30 (22) : 6218 - 6224
  • [25] Synthesis and Structure of 1,4-Diphenyl-3-methyl-1,2,3-triazol-5-ylidene Palladium Complexes and Application in Catalytic Hydroarylation of Alkynes
    Saravanakumar, Rajendran
    Ramkumar, Venkatachalam
    Sankararaman, Sethuraman
    ORGANOMETALLICS, 2011, 30 (06) : 1689 - 1694
  • [26] A Cytotoxic Bis(1,2,3-triazol-5-ylidene)carbazolide Gold(III) Complex Targets DNA by Partial Intercalation
    van der Westhuizen, Danielle
    Slabber, Cathryn A.
    Fernandes, Manuel A.
    Joubert, Daniel F.
    Kleinhans, George
    van der Westhuizen, C. Johan
    Stander, Andre
    Munro, Orde Q.
    Bezuidenhout, Daniela, I
    CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (32) : 8295 - 8307
  • [27] A Triarylated 1,2,3-Triazol-5-ylidene Ligand with a Redox-Active Ferrocenyl Substituent for Rhodium(I)-Catalyzed Hydroformylation of 1-Octene
    Aucamp, Danielle
    Witteler, Tim
    Dielmann, Fabian
    Siangwata, Shepherd
    Liles, David C.
    Smith, Gregory S.
    Bezuidenhout, Daniela I.
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2017, (09) : 1227 - 1236
  • [28] A Hemilabile and Cooperative N-Donor-Functionalized 1,2,3-Triazol-5-Ylidene Ligand for Alkyne Hydrothiolation Reactions
    Strydom, Ian
    Guisado-Barrios, Gregorio
    Fernandez, Israel
    Liles, David C.
    Peris, Eduardo
    Bezuidenhout, Daniela I.
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (06) : 1393 - 1401
  • [29] Mechanochemical Synthesis of Tripodal Tris[4-(1,2,3-triazol-5-ylidene)methyl]amine Mesoionic Carbene Ligands and Their Complexation with Silver(I)
    Ang, Zhi Zhong
    Laxmi, Shoba
    Leon, Felix
    Kooij, Josephine E. M.
    Garcia, Felipe
    England, Jason
    INORGANIC CHEMISTRY, 2021, 60 (06) : 3556 - 3564
  • [30] Gold(I) and Palladium(II) Complexes of 1,3,4-Trisubstituted 1,2,3-Triazol-5-ylidene "Click" Carbenes: Systematic Study of the Electronic and Steric Influence on Catalytic Activity
    Wright, James R.
    Young, Paul C.
    Lucas, Nigel T.
    Lee, Ai-Lan
    Crowley, James D.
    ORGANOMETALLICS, 2013, 32 (23) : 7065 - 7076