Iron-Catalyzed C(sp2)-C(sp3) Cross-Coupling Reactions of Di(hetero)arylmanganese Reagents and Primary and Secondary Alkyl Halides

被引:3
|
作者
Hofmayer, Maximilian S. [1 ]
Hammann, Jeffrey M. [1 ]
Cahiez, Gerard [2 ]
Knochel, Paul [1 ]
机构
[1] Ludwig Maximilians Univ Munchen, Dept Chem, Butenandtstr 5-13, D-81377 Munich, Germany
[2] Chim ParisTech, CNRS, Chim ParisTech, 11 Rue Pierre & Marie Curie, F-75005 Paris, France
关键词
iron; catalysis; cross-coupling; manganese; alkyl halides; ARYL-GRIGNARD-REAGENTS; HETEROCYCLIC CHLORIDES; ARYLCOPPER REAGENTS; BROMIDES; ALKENYL; FLUORIDES; TOSYLATES; ARYLATION; ALCOHOLS;
D O I
10.1055/s-0036-1590891
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An iron-catalyzed cross-coupling between di(hetero)arylmanganese reagents and primary and secondary alkyl halides is reported. No rearrangement of secondary alkyl halides to unbranched products was observed in these C-C bond-forming reactions.
引用
收藏
页码:65 / 70
页数:6
相关论文
共 50 条
  • [1] Iron-Catalyzed C(sp2)-C(sp3) Cross-Coupling of Alkyl Grignard Reagents with Polyaromatic Tosylates
    Piontek, Aleksandra
    Szostak, Michal
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (48) : 7271 - 7276
  • [2] Iron-Catalyzed C(sp2)-C(sp3) Cross-Coupling of Aryl Chlorobenzoates with Alkyl Grignard Reagents
    Bisz, Elwira
    Szostak, Michal
    [J]. MOLECULES, 2020, 25 (01):
  • [3] Iron-Catalyzed C(sp2)-C(sp3) Cross-Coupling of Chlorobenzenesulfonamides with Alkyl Grignard Reagents: Entry to Alkylated Aromatics
    Bisz, Elwira
    Szostak, Michal
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (03): : 1640 - 1646
  • [4] Cobalt-Catalyzed C(sp2)-C(sp3) Cross-Coupling Reactions of Diarylmanganese Reagents with Secondary Alkyl Iodides
    Hofmayer, Maximilian S.
    Hammann, Jeffrey M.
    Haas, Diana
    Knochel, Paul
    [J]. ORGANIC LETTERS, 2016, 18 (24) : 6456 - 6459
  • [5] Direct C(sp2)-C(sp3) Cross-Coupling of Diaryl Zinc Reagents with Benzylic, Primary, Secondary, and Tertiary Alkyl Halides
    Dunsford, Jay J.
    Clark, Ewan R.
    Ingleson, Michael J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (19) : 5688 - 5692
  • [6] Iron-catalyzed C(sp2)-C(sp3) cross-coupling at low catalyst loading
    Bisz, Elwira
    Kardela, Marlena
    Piontek, Aleksandra
    Szostak, Michal
    [J]. CATALYSIS SCIENCE & TECHNOLOGY, 2019, 9 (05) : 1092 - 1097
  • [7] A TMEDA-Iron Adduct Reaction Manifold in Iron-Catalyzed C(sp2)-C(sp3) Cross-Coupling Reactions
    Bakas, Nikki J.
    Sears, Jeffrey D.
    Brennessel, William W.
    Neidig, Michael L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (15)
  • [8] Iron-Catalyzed C(sp2)-C(sp3) Cross-Coupling of Chlorobenzamides with Alkyl Grignard Reagents: Development of Catalyst System, Synthetic Scope, and Application
    Bisz, Elwira
    Szostak, Michal
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (01) : 85 - 95
  • [9] Palladium-Catalyzed C(sp3) C(sp2) Cross-Coupling of (Trimethylsilyl)methyllithium with (Hetero)Aryl Halides
    Heijnen, Dorus
    Hornillos, Valentin
    Corbet, Brian P.
    Giannerini, Massimo
    Feringa, Ben L.
    [J]. ORGANIC LETTERS, 2015, 17 (09) : 2262 - 2265
  • [10] Role of TMEDA in Iron-Catalyzed C(sp2)-C(sp3) Cross-Coupling Reactions: A Mechanistic Study Using DFT Calculations
    Wan, Xin
    Zhao, Tianchu
    Ren, Qinghua
    Zhou, Gangchang
    [J]. ORGANOMETALLICS, 2024, 43 (04) : 449 - 456