Yoshikai, N. : 2023 Science of Synthesis, 2023/3: Base-Metal Catalysis 2 DOI: 10.1055/sos-SD-239-00001
Base-Metal Catalysis 2

2.9 Iron-Catalyzed Cross Coupling of Aryl and Vinyl Electrophiles

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Book

Editor: Yoshikai, N.

Authors: Adak, L. ; Aoki, S.; Banerjee, S. ; Bedford, R. B. ; Cheng, Z.; Costas, M. ; Gao, M.; Garai, B.; Ge, S. ; Gosmini, C. ; Hota, S. K.; Ilies, L. ; Jindal, A.; Kawanaka, Y.; Li, H. ; Li, M.; Liu, Q. ; Lu, Z. ; Mandal, R.; Matsunaga, S. ; Murarka, S. ; Nakamura, M. ; Nolla-Saltiel, R. ; Ollevier, T. ; Palone, A. ; Panda, S. P.; Sahoo, S.; Sang, J.; Schiltz, P.; Shenvi, R. A. ; Sundararaju, B. ; van der Puyl, V. ; Vicens, L. ; Wang, C. ; Wang, Y. ; Yang, X.; Yang, Y.; Yoshikai, N. ; Yoshino, T. ; Zeng, X. ; Zhang, G.

Title: Base-Metal Catalysis 2

Print ISBN: 9783132455030; Online ISBN: 9783132455054; Book DOI: 10.1055/b000000440

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

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Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

 


Abstract

This review focuses on cross-coupling methodologies that utilize aryl and vinyl electrophiles relying on iron-based catalysts. We have outlined the most relevant and better-established methodologies; leading to the discussion of significant cases based on hard nucleophiles, with the number of examples dropping with their increasing softness. In addition, we describe several useful transformations based on reactive unsaturated nucleophiles, such as acetylenes and alkenes.

 
  • 6 Guideline on the specification limits for residues of metal catalysts or metal impurities EMA/CHMP/ICH353 369/2013; (2016); https://www.ema.europa.eu/en/ich-q3d-elemental-impurities.
  • 12 Zhou J, Berthel JHJ, Kuntze-Fechner MW, Friedrich A, Marder TB, Radius U. J. Org. Chem. 2016; 81: 5789
  • 27 Nakamura E, Hatakeyama T, Ito S, Kentaro I, Ilies L, Masaharu N. Org. React. (N. Y.) 2014; 83: 1
  • 28 Nakamura M, Ito S, Modern Arylation Methods Ackermann L. Wiley-VCH Weinheim, Germany 2009; 155
  • 31 Tamura M, Kochi J. Synthesis 1971; 303
  • 36 Cahiez G, Avedissian H. Synthesis 1998; 1199
  • 38 Dohle W, Kopp F, Cahiez G, Knochel P. Synlett 2001; 1901
  • 45 Bedford RB, Bruce DW, Frost RM, Hird M. Chem. Commun. (Cambridge) 2004; 2822
  • 46 Bedford RB, Bruce DW, Frost RM, Hird M. Chem. Commun. (Cambridge) 2005; 4161
  • 54 Agata R, Iwamoto T, Nakagawa N, Isozaki K, Hatakeyama T, Takaya H, Nakamura M. Synthesis 2015; 47: 1733
  • 55 Aynetdinova D, Callens MC, Hicks HB, Poh CYX, Shennan BDA, Boyd AM, Lim ZH, Leitch JA, Dixon DJ. Chem. Soc. Rev. 2021; 50: 5517
  • 57 Buono FG, Zhang Y, Tan Z, Brusoe A, Yang BS, Lorenz JC, Giovannini R, Song JJ, Yee NK, Senanayake CH. Eur. J. Org. Chem. 2016; 2599
  • 58 Wei XJ, Abdiaj I, Sambiagio C, Li C, Zysman-Colman E, Alcázar J, Noël T. Angew. Chem. Int. Ed. 2019; 58: 13030
  • 63 Li B.-J, Li X, Wu Z.-H, Guan B.-T, Sun C.-L, Wang B.-Q, Shi Z.-J. J. Am. Chem. Soc. 2009; 131: 14656
  • 69 Protti S, Fagnoni M. Chem. Commun. (Cambridge) 2008; 3611
  • 84 Bedford RB, Hall MA, Hodges GR, Huwe M, Wilkinson MC. Chem. Commun. (Cambridge) 2009; 6430
  • 85 Adams CJ, Bedford RB, Carter E, Gower NJ, Haddow MF, Harvey JN, Huwe M, Cartes MÁ, Mansell SM, Mendoza C, Murphy DM, Neeve EC, Nunn J. J. Am. Chem. Soc. 2012; 134: 10333
  • 86 Messinis AM, Luckham SLJ, Wells PP, Gianolio D, Gibson EK, OʼBrien HM, Sparkes HA, Davis SA, Callison J, Elorriaga D, Hernandez-Fajardo O, Bedford RB. Nat. Catal. 2019; 2: 123
  • 89 OʼBrien HM, Manzotti M, Abrams RD, Elorriaga D, Sparkes HA, Davis SA, Bedford RB. Nat. Catal. 2018; 1: 429