[Pd(IPr*(acac)Cl]: An Easily Synthesized, Bulky Precatalyst for C-N Bond Formation

被引：77
|
作者：
Meiries, Sebastien [1 ]
Chartoire, Anthony [1 ]
Slawin, Alexandra M. Z. [1 ]
Nolan, Steven P. [1 ]
机构：
[1] Univ St Andrews, EaStCHEM Sch Chem, St Andrews KY16 9ST, Fife, Scotland
来源：
ORGANOMETALLICS | 2012年 / 31卷 / 08期
关键词：
PALLADIUM-CATALYZED AMINATION; HETEROCYCLIC CARBENE LIGANDS; CROSS-COUPLING REACTIONS; TEMPERATURE SUZUKI-MIYAURA; ARYL CHLORIDES; BUCHWALD-HARTWIG; RESTRICTED FLEXIBILITY; (NHC)PD(ALLYL)CL NHC; COMPLEXES; EFFICIENT;
D O I：
10.1021/om300205c
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
A very straightforward synthesis of [Pd(IPr*)(acac)Cl] has been developed from commercially available Pd(acac)(2) and the easily prepared IPr*center dot HCl (acac = acetylacetonate; IPr* = N,N'-bis(2,6-bis(diphenylmethyl)-4-methylphenyl)imidazol-2-ylidene). The reactivity of the resulting complex [Pd(IPr*)(acac)Cl] (1) as a highly active Pd-II precatalyst for the Buchwald-Hartwig arylamination coupling has been explored. A wide range of substrates with varying electronic and steric demands of both coupling partners has been screened successfully. The chemoselectivity of the reaction was also explored by using aryl heterodihalides.
引用
收藏
页码：3402 / 3409
页数：8
相关论文
共 50 条
  • [41] A photochemical electrocyclization of the benzothiazolylphenylethenes involving a C-N bond formation
    Fedorova, Olga A.
    Gulakova, Elena N.
    Fedoroy, Yuri V.
    Lobazova, Irina E.
    Alfirnov, Michael V.
    Jonusauskas, G.
    JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2008, 196 (2-3) : 239 - 245
  • [42] Borrowing hydrogen -: C-N bond formation from alcohols
    Lamb, Gareth W.
    Williams, Jonathan M. J.
    CHIMICA OGGI-CHEMISTRY TODAY, 2008, 26 (03) : 17 - 19
  • [43] Allylic amination via decarboxylative C-N bond formation
    Mellegaard-Waetzig, SR
    Rayabarapu, DK
    Tunge, JA
    SYNLETT, 2005, (18) : 2759 - 2762
  • [44] Convenient synthesis of N-1-alkyl benzimidazoles via Pd catalyzed C-N bond formation and cyclization
    Bie, Fusheng
    Yao, Yongfeng
    Cao, Han
    Shi, Yijun
    Yan, Peng
    Ma, Jie
    Han, Ying
    Liu, Xuejing
    SYNTHETIC COMMUNICATIONS, 2021, 51 (15) : 2387 - 2396
  • [45] Regioselective C-N bond formation via gold catalysis
    Marchetti, Louis
    Kantak, Abhishek
    Davis, Riley
    DeBoef, Brenton
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [46] Application of indole-based monophosphine in ppm level Pd-catalyzed C-N bond formation
    Li, Cheuk Long
    Tse, Man Ho
    Choy, Pui Ying
    Kwong, Fuk Yee
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2024, 1011
  • [47] N-fluorobenzenesulfonimide: An efficient nitrogen source for C-N bond formation
    Li, Yan
    Zhang, Qian
    Synthesis (Germany), 2014, 46 (02)
  • [48] Diastereoselective Oxidative C-N/C-O and C-N/C-N Bond Formation Tandems Initiated by Visible Light: Synthesis of Fused N-Arylindolines
    Morris, Scott A.
    Nguyen, Theresa H.
    Zheng, Nan
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (10) : 2311 - 2316
  • [49] Development and investigation of Pd-catalyzed C-N bond formation: Application to the synthesis of an active pharmaceutical ingredient
    Milne, Jacqueline E.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [50] Development and investigation of a Pd-catalyzed C-N bond formation: Application to the synthesis of an active pharmaceutical ingredient
    Milne, Jacqueline
    Allgeier, Alan
    Guram, Anil
    Baum, Jean
    Murry, Jerry
    Colyer, John
    Wang, Xiang
    Payack, Joseph
    Storz, Thomas
    Seran, Mine Dilmeghani
    Hwang, Tsang-Lin
    Shaw, Bradley
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
12345