The influence of the ligand chelate effect on iron-amine-catalysed Kumada cross-coupling

被引:29
作者
Bedford, Robin B. [1 ]
Brenner, Peter B. [1 ]
Elorriaga, David [1 ]
Harvey, Jeremy N. [2 ]
Nunn, Joshua [1 ]
机构
[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
[2] Univ Leuven, KU Leuven, Dept Chem, Quantum Chem & Phys Chem Sect, Celestijnenlaan 200F,Box 2404, Leuven, Belgium
基金
英国工程与自然科学研究理事会;
关键词
ARYL GRIGNARD-REAGENTS; ALKYL-HALIDES; ALKENYL HALIDES; COMPLEXES; DERIVATIVES; BENZYL; TMEDA;
D O I
10.1039/c6dt01823h
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The application of a variety of iron complexes with chelating amine ligands as pre-catalysts in the representative cross-coupling of 4-tolylmagnesium bromide with cyclohexyl bromide was investigated. The results from this study indicate the performance of the pre-catalyst is inversely proportional to the strength of the chelate or macrocyclic effect of the amine ligand, as determined by the propensity of the ligand to be displaced from the iron centre by reaction with excess benzyl magnesium chloride. The findings from this study are consistent with a catalytic cycle wherein the chelating amine ligand is not coordinated to the iron centre during turnover.
引用
收藏
页码:15811 / 15817
页数:7
相关论文
共 25 条
[1]   Catalytic and Organometallic Chemistry of Earth-Abundant Metals [J].
Albrecht, Martin ;
Bedford, Robin ;
Plietker, Bernd .
ORGANOMETALLICS, 2014, 33 (20) :5619-5621
[2]   Synthesis, reactivity, and solid state structures of four-coordinate iron(II) and manganese(II) alkyl complexes [J].
Bart, SC ;
Hawrelak, EJ ;
Schmisseur, AK ;
Lobkovsky, E ;
Chirik, PJ .
ORGANOMETALLICS, 2004, 23 (02) :237-246
[3]   Iron Catalysis in Organic Synthesis [J].
Bauer, Ingmar ;
Knoelker, Hans-Joachim .
CHEMICAL REVIEWS, 2015, 115 (09) :3170-3387
[4]  
Bedford R. B., 2005, CHEM COMMUN, V4161
[5]   Iron nanoparticles in the coupling of alkyl halides with aryl Grignard reagents [J].
Bedford, RB ;
Betham, M ;
Bruce, DW ;
Davis, SA ;
Frost, RM ;
Hird, M .
CHEMICAL COMMUNICATIONS, 2006, (13) :1398-1400
[6]   The Development of Iron Catalysts for Cross-Coupling Reactions [J].
Bedford, Robin B. ;
Brenner, Peter B. .
IRON CATALYSIS II, 2015, 50 :19-46
[7]   How Low Does Iron Go? Chasing the Active Species in Fe-Catalyzed Cross-Coupling Reactions [J].
Bedford, Robin B. .
ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (05) :1485-1493
[8]   Expedient Iron-Catalyzed Coupling of Alkyl, Benzyl and Allyl Halides with Arylboronic Esters [J].
Bedford, Robin B. ;
Brenner, Peter B. ;
Carter, Emma ;
Carvell, Thomas W. ;
Cogswell, Paul M. ;
Gallagher, Timothy ;
Harvey, Jeremy N. ;
Murphy, Damien M. ;
Neeve, Emily C. ;
Nunn, Joshua ;
Pye, Dominic R. .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (26) :7935-7938
[9]   TMEDA in Iron-Catalyzed Kumada Coupling: Amine Adduct versus Homoleptic "ate" Complex Formation [J].
Bedford, Robin B. ;
Brenner, Peter B. ;
Carter, Emma ;
Cogswell, Paul M. ;
Haddow, Mairi F. ;
Harvey, Jeremy N. ;
Murphy, Damien M. ;
Nunn, Joshua ;
Woodall, Christopher H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (07) :1804-1808
[10]   Iron-catalyzed alkylations of aromatic Grignard reagents [J].
Cahiez, Gerard ;
Habiak, Vanessa ;
Duplais, Christophe ;
Moyeux, Alban .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (23) :4364-4366