Iron Phthalocyanine

Introduction

Iron phthalocyanine (FePc) complexes are structurally related to porphyrin complexes; phthalocyanines have been used as alternative catalysts because they are cheaper and more stable to degradation. FePc is widely used in a variety of catalytic transformations,[1] including N-alkylation,[2] C–H amination,[3] C–C bond formation,[4] preparation of esters[5] and oximes,[6] reduction,[7] oxidation,[8] [9] and radical reactions.[10] Although FePc is particularly studied as a catalyst for organic reactions, this particular reagent is also described in many other applications. For example, FePc complexes are efficient catalyst for the charge/discharge process in lithium–oxygen large-capacity batteries.[11] The following literature data indicate that FePc displays a strong bibliographic background in a wide variety of reactions and is currently considering as an active and ‘hot’ research topic. On overview of typical iron phthalocyanine syntheses is shown in Scheme [1].

Scheme 1 Preparation of FePc complexes from cyclotetramerization of common precursors. Reagents and conditions: (a) iron salt, Δ; (b) iron salt, urea, catalyst, Δ.

• References

• 1 Sorokin AB. Chem. Rev. 2013; 113: 8152
• 2 Bala M, Verma PK, Sharma U, Kumar N, Singh B. Green Chem. 2013; 15: 1687
• 3 Paradine SM, White MC. J. Am. Chem. Soc. 2012; 134: 2036
• 4 Lamar AA, Nicholas KM. Tetrahedron 2009; 65: 3829
• 5 Taniguchi T, Hirose D, Ishibashi H. ACS Catal. 2011; 1: 1469
• 6 Prateeptongkum S, Jovel I, Jackstell R, Vogl N, Weckbecker C, Beller M. Chem. Commun. 2009; 1990
• 7 Kudrik E, Makarov SV, Zahl A, van Eldik R. Inorg. Chem. 2005; 44: 6470
• 8 Sugimori T, Horike SI, Tsumura S, Hande M, Kasuga K. Inorg. Chem. Acta 1998; 283: 275
• 9 Leggans EK, Barker TJ, Duncan KK, Boger DL. Org. Lett. 2012; 14: 1428
• 10 Taniguchi T, Goto N, Nishibata A, Ishibashi H. Org. Lett. 2010; 12: 112
• 11 Sun D, Shen Y, Zhang W, Yu L, Yi Z, Yin W, Wang D, Huang Y, Wang D, Goodenough JB. J. Am. Chem. Soc. 2014; 136: 8941