Selective Kumada biaryl cross-coupling reaction enabled by an iron(III) alkoxide-N-heterocyclic carbene catalyst system

被引：49
|
作者：
Chua, Yi-Yuan [1 ]
Duong, Hung A. [1 ]
机构：
[1] Agcy Sci Technol & Res, Inst Chem & Engn Sci, Singapore 138665, Singapore
来源：
CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 61期
关键词：
GRIGNARD-REAGENTS; HETEROARYL HALIDES; IRON; ARYL; COBALT; CHLORIDES; LIGANDS; CHEMISTRY; CENTERS;
D O I：
10.1039/c4cc02930e
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A catalyst system comprising Fe-2((OBu)-Bu-t)(6) and an N-heterocyclic carbene ligand enables efficient syntheses of (hetero)biaryls from the reactions of aryl Grignard reagents with a diverse spectrum of (hetero)aryl chlorides. Amongst the alkoxide and amide counterions investigated, tert-butoxide was the most effective in inhibiting the homocoupling of arylmagnesiums.
引用
收藏
页码：8424 / 8427
页数：4
相关论文
共 50 条
  • [1] A Highly Active Cobalt Catalyst System for Kumada Biaryl Cross-Coupling
    Wu, Wenqin
    Duong, Hung A.
    [J]. SYNLETT, 2018, 29 (09) : 1199 - 1202
  • [2] An N-heterocyclic carbene based MOF catalyst for Sonogashira cross-coupling reaction
    Ezugwu, Chizoba I.
    Mousavi, Bibimaryam
    Asrafa, Md. Ali
    Mehta, Akshay
    Vardhan, Harsh
    Verpoort, Francis
    [J]. CATALYSIS SCIENCE & TECHNOLOGY, 2016, 6 (07) : 2050 - 2054
  • [3] The first Negishi cross-coupling reaction of two alkyl centers utilizing a pd-n-heterocyclic carbene (NHC) catalyst
    Hadei, N
    Kantchev, EAB
    O'Brien, CJ
    Organ, MG
    [J]. ORGANIC LETTERS, 2005, 7 (17) : 3805 - 3807
  • [4] A Bulky Chiral N-Heterocyclic Carbene Palladium Catalyst Enables Highly Enantioselective Suzuki-Miyaura Cross-Coupling Reactions for the Synthesis of Biaryl Atropisomers
    Shen, Di
    Xu, Youjun
    Shi, Shi-Liang
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (37) : 14938 - 14945
  • [5] Cellulose-supported N-heterocyclic carbene-palladium catalyst: Synthesis and its applications in the Suzuki cross-coupling reaction
    Wang, Xiaoxia
    Hu, Peibo
    Xue, Fengjun
    Wei, Yuping
    [J]. CARBOHYDRATE POLYMERS, 2014, 114 : 476 - 483
  • [6] First Kumada reaction of alkyl chlorides using N-heterocyclic carbene/palladium catalyst systems
    Frisch, AC
    Rataboul, F
    Zapf, A
    Beller, M
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 687 (02) : 403 - 409
  • [7] Cross-coupling of Aryl Sulfides Powered by N-Heterocyclic Carbene Ligands
    Gao, Ke
    Otsuka, Shinya
    Baralle, Alexandre
    Nogi, Keisuke
    Yorimitsu, Hideki
    Osuka, Atsuhiro
    [J]. JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2016, 74 (11) : 1119 - 1127
  • [8] Pd-N-heterocyclic carbene (NHC) catalysts for cross-coupling reactions
    Kantchev, Eric Assen B.
    O'Brien, Christopher J.
    Organ, Michael G.
    [J]. ALDRICHIMICA ACTA, 2006, 39 (04) : 97 - 111
  • [9] Highly Selective Biaryl Cross-Coupling Reactions between Aryl Halides and Aryl Grignard Reagents: A New Catalyst Combination of N-Heterocyclic Carbenes and Iron, Cobalt, and Nickel Fluorides
    Hatakeyama, Takuji
    Hashimoto, Sigma
    Ishizuka, Kentaro
    Nakamura, Masaharu
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (33) : 11949 - 11963
  • [10] Benzimidazole-based palladium-N-heterocyclic carbene: a useful catalyst for C-C cross-coupling reaction at ambient condition
    Gupta, Sumanta
    Basu, Basudeb
    Das, Sajal
    [J]. TETRAHEDRON, 2013, 69 (01) : 122 - 128
12345