Synthesis 2015; 47(12): 1696-1705
DOI: 10.1055/s-0034-1380195
short review
© Georg Thieme Verlag Stuttgart · New York

Recent Advances in Iron-Catalyzed Csp2–Csp2 Cross-Couplings

Olesya M. Kuzmina
a   Department of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, Haus F, 81377 München, Germany   Email: paul.knochel@cup.uni-muenchen.de
,
Andreas K. Steib
a   Department of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, Haus F, 81377 München, Germany   Email: paul.knochel@cup.uni-muenchen.de
,
Alban Moyeux
b   Institut de Recherche de Chimie Paris, CNRS – Chimie ParisTech, 11 rue Pierre et Marie Curie, 75005 Paris, France   Email: gerard.cahiez@chimie-paristech.fr
c   Université Paris 13, Sorbonne Paris Cité, 74 rue Marcel Cachin, 93017 Bobigny, France
,
Gérard Cahiez*
b   Institut de Recherche de Chimie Paris, CNRS – Chimie ParisTech, 11 rue Pierre et Marie Curie, 75005 Paris, France   Email: gerard.cahiez@chimie-paristech.fr
,
Paul Knochel*
a   Department of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, Haus F, 81377 München, Germany   Email: paul.knochel@cup.uni-muenchen.de
› Author Affiliations
Further Information

Publication History

Received: 20 December 2014

Accepted: 11 March 2015

Publication Date:
02 April 2015 (online)


Abstract

The present review article highlights recent progress in the field of iron-catalyzed cross-coupling reactions between Csp² centers. The reaction scope of various iron-catalyzed couplings between aromatic Grignard reagents and unsaturated halides is described and some mechanistic insights are given.

1 Introduction

2 Historical Work

3 Iron-Catalyzed Homocouplings of Aryl Organometallics

4 Iron-Catalyzed sp2–sp2 Cross-Couplings

4.1 Arylcopper Reagents as Nucleophiles

4.2 Arylmagnesium Reagents as Nucleophiles

4.2.1 Couplings with Alkenyl Halides

4.2.2 Couplings with Heteroaryl Halides

4.2.3 Coupling with Aryl Halides

5 Conclusion

 
  • References


    • For selected reviews on iron-catalyzed cross-coupling reactions, see:
    • 1a Bolm C, Legros J, Paih JL, Zani L. Chem. Rev. 2004; 104: 6217
    • 1b Shinokuo H, Oshima K. Eur. J. Org. Chem. 2004; 2081
    • 1c Fürstner A, Martin R. Chem. Lett. 2005; 34: 624
    • 1d Yorimitsu H, Oshima K. Pure Appl. Chem. 2006; 78: 441
    • 1e Plietker B. Iron Catalysis in Organic Chemistry: Reactions and Applications. Wiley-VCH; Weinheim: 2008
    • 1f Enthaler S, Junge K, Beller M. Angew. Chem. Int. Ed. 2008; 47: 3317
    • 1g Sherry BD, Fürstner A. Acc. Chem. Res. 2008; 41: 1500
    • 1h Correa A, Mancheño OG, Bolm C. Chem. Soc. Rev. 2008; 37: 1108
    • 1i Bolm C. Nat. Chem. 2009; 1: 420
    • 1j Fürstner A. Angew. Chem. Int. Ed. 2009; 48: 1364
    • 1k Czaplik WM, Mayer M, Cvengroš J, von Wangelin AJ. ChemSusChem 2009; 2: 396
    • 1l Nakamura E, Yoshikai N. J. Org. Chem. 2010; 75: 6061
    • 1m Nakamura E, Hatakeyama T, Ito S, Ishizuka K, Ilies L, Nakamura M. Iron-Catalyzed Cross-Coupling Reactions . In Organic Reactions . Vol. 83. Wiley-VCH; Weinheim: 2013: 1-120

      For selected publications on mechanistic investigations of iron-catalyzed coupling reactions, see:
    • 2a Bogdanović B, Schwickardi M. Angew. Chem. Int. Ed. 2000; 39: 4610
    • 2b Fürstner A, Martin R, Krause H, Seidel G, Goddard R, Lehmann CW. J. Am. Chem. Soc. 2008; 130: 8773
    • 2c Kleimark J, Hedström A, Larsson P.-F, Johansson C, Norrby P.-O. ChemCatChem 2009; 1: 152
    • 2d Hedström A, Bollmann U, Bravidor J, Norrby P.-O. Chem. Eur. J. 2011; 17: 11991
    • 2e Adams CJ, Bedford RB, Carter E, Gower NJ, Haddow MF, Harvey JN, Huwe M, Ángeles Cartes M, Mansell SM, Mendoza C, Murphy DM, Neeve EC, Nunn J. J. Am. Chem. Soc. 2012; 134: 10333
    • 2f Schoch R, Desens W, Werner T, Bauer M. Chem. Eur. J. 2013; 19: 15816
    • 2g Lefèvre G, Jutand A. Chem. Eur. J. 2014; 20: 4796
    • 2h Daifuku SL, Al-Afyouni MH, Snyder BE. R, Kneebone JL, Neidig ML. J. Am. Chem. Soc. 2014; 136: 9132
    • 2i Al-Afyouni MH, Fillman KL, Brennessel WW, Neidig ML. J. Am. Chem. Soc. 2014; 136: 15457
    • 2j Bedford RB, Brenner PB, Carter E, Cogswell PM, Haddow MF, Harvey JN, Murphy DM, Nunn J, Woodall CH. Angew. Chem. Int. Ed. 2014; 53: 1804
  • 3 Gilman H, Lichtenwalter M. J. Am. Chem. Soc. 1939; 61: 957
  • 4 Kharash MS, Fields EK. J. Am. Chem. Soc. 1941; 63: 2316
    • 5a Kumada M, Kochi JK. J. Am. Chem. Soc. 1971; 93: 1487
    • 5b Kochi JK, Tamura M. Synthesis 1971; 303
    • 5c Tamura M, Kochi JK. Bull. Chem. Soc. Jpn. 1971; 44: 306
    • 5d Tamura M, Kochi J. J. Organomet.. Chem. 1971; 31: 289
    • 5e Kochi JK. Acc. Chem. Res. 1974; 7: 351
    • 5f Smith RS, Kochi JK. J. Org. Chem. 1976; 41: 502
  • 6 Felkin H, Meunier B. J. Organomet. Chem. 1978; 146: 169
  • 7 Nagano T, Hayashi T. Org. Lett. 2005; 7: 491
  • 8 Cahiez G, Chaboche C, Mahuteau-Betzer F, Ahr M. Org. Lett. 2005; 7: 1943
  • 9 Xu X, Cheng D, Pei W. J. Org. Chem. 2006; 71: 6637
  • 10 Zhang Y.-Y, Lin J.-D, Xu X.-L, Li J.-H. Synth. Commun. 2010; 40: 2556
  • 11 Cahiez G, Moyeux A, Buendia J, Duplais C. J. Am. Chem. Soc. 2007; 129: 13788
  • 12 Liu W, Lei A. Tetrahedron Lett. 2008; 49: 610
  • 13 Molie Y, Mascaro E, Nador F, Vitale C, Radivoy G. Synth. Commun. 2008; 38: 3861
  • 14 Kude K, Hayase S, Kawatsura M, Itoh T. Heteroat. Chem. 2011; 22: 397
  • 15 Kiefer G, Jeanbourquin L, Severin K. Angew. Chem. Int. Ed. 2013; 52: 6302
  • 16 Toummini D, Ouazzani F, Taillefer M. Org. Lett. 2013; 15: 4690
  • 17 Wu J, Dai W, Farnaby JH, Hazari N, Le Roy JJ, Mereacre V, Murugesu M, Powell AK, Takase MK. Dalton Trans. 2013; 42: 7404
  • 18 Knochel P, Yeh MC. P, Berk SC, Talbert J. J. Org. Chem. 1988; 53: 2392
  • 19 Sapountzis I, Lin W, Kofink CC, Despotopoulou C, Knochel P. Angew. Chem. Int. Ed. 2005; 44: 1654
  • 20 Dunet G, Knochel P. Synlett 2006; 407
  • 21 Kofink CC, Blank B, Pagano S, Götz N, Knochel P. Chem. Commun. 2007; 1954
  • 22 Fabre J.-L, Julia M, Verpeaux J.-N. Tetrahedron Lett. 1982; 23: 2469
  • 23 Neumann SM, Kochi JK. J. Org. Chem. 1975; 40: 599
  • 24 Molander GA, Rahn BJ, Shubert DC. Tetrahedron Lett. 1983; 24: 5449
  • 25 Cahiez G, Avedissian H. Synthesis 1998; 1199
  • 26 Dohle W, Kopp F, Cahiez G, Knochel P. Synlett 2001; 1901
  • 27 Østergaard N, Pedersen BT, Skjærbæk N, Vedsø P, Begtrup M. Synlett 2002; 1889
  • 28 Scheiper B, Bonnekessel M, Krause H, Fürstner A. J. Org. Chem. 2004; 69: 3943
  • 29 Itami K, Higashi S, Mineno M, Yoshida J.-i. Org. Lett. 2005; 7: 1219
  • 30 Tewari N, Maheshwari N, Medhane R, Nizar H, Prasad M. Org. Process Res. Dev. 2012; 16: 1566
  • 31 Fürstner A, Leitner A, Méndez M, Krause H. J. Am. Chem. Soc. 2002; 124: 13856
  • 32 Quintin J, Franck X, Hocquemiller R, Figadère B. Tetrahedron Lett. 2002; 43: 3547
  • 33 Korn TJ, Cahiez G, Knochel P. Synlett 2003; 1892
  • 34 Boully L, Darabantu M, Turck A, Plé N. J. Heterocycl. Chem. 2005; 42: 1423
  • 35 Gøgsig TM, Lindhardt AT, Skrydstrup T. Org. Lett. 2009; 11: 4886
  • 36 Colacino E, Benakki H, Guenoun F, Martinez J, Lamaty F. Synth. Commun. 2009; 39: 1583
  • 37 Zhang Y, Liu B, Wu HY, Chen WZ. Chin. Sci. Bull. 2012; 57: 2368
  • 38 Kuzmina OM, Steib AK, Flubacher D, Knochel P. Org. Lett. 2012; 14: 4818
  • 39 Kuzmina OM, Steib AK, Markiewicz JT, Flubacher D, Knochel P. Angew. Chem. Int. Ed. 2013; 52: 4945
  • 40 Hatakeyama T, Nakamura M. J. Am. Chem. Soc. 2007; 129: 9844
  • 41 Hatakeyama T, Hashimoto S, Ishizuka K, Nakamura M. J. Am. Chem. Soc. 2009; 131: 11949
  • 42 Gülak S, von Wangelin AJ. Angew. Chem. Int. Ed. 2012; 51: 1357
  • 43 Chua Y.-Y, Duong HA. Chem. Commun. 2014; 50: 8424
  • 44 Agrawal T, Cook SP. Org. Lett. 2014; 16: 5080