Highly Functionalized Ferrocenes

Abstract

Ferrocene is unique among organometallic compounds, and serves notably as a versatile platform towards the production of ligands useful to promote transition metals chemistry. A general limiting aspect of the synthesis of ferrocene derivatives is the efficient access to sophisticated highly functionalized polysubstituted ferrocenes, i.e. bearing four or more substituents replacing hydrogen atoms on the cyclopentadienyl rings. These ferrocene derivatives can bear various functional or/and structuring spectator substituents. Their preparation involves synthetic difficulties resulting from the need of multiple functionalizations coexisting altogether, and satisfying functional group compatibility and high selectivity issues. In the last decades, our group initially designed highly functionalized polyphosphines and hybrid ligands (1,1′,3,3′-tetrafunctionalized

Forever young: the first seventy years of ferrocene

“…, by varying the phosphorus substituents and introducing additional alkyl or phosphine substituents to the ferrocene core). 62,66 Examples of such compounds reported recently include a dppf analogue with a “cage phosphine” 67 substituent 6 , 68 diphosphines with P-alkynyl groups 7 69 and bulky ligands 8 70 and 9 71 (Scheme 4).…”

Ferrocene functionalized enantiomerically pure Schiff bases and their Zn(ii) and Pd(ii) complexes: a spectroscopic, crystallographic, electrochemical and computational investigation

“…Ferrocene [Fe(Z 5 -C 5 H 5 ) 2 ] (FcH), the iconic organometallic complex discovered 70 years ago, [1][2][3][4][5] displays exceptional properties, 6 and research on ferrocene and its derivatives continues to demonstrate great interest and vitality. [7][8][9] Indeed, ferrocene is fascinating due to its stability under aerobic, moist and photochemical conditions, its thermodynamic robustness, its unique structural properties such as adequate rigidity and steric bulkiness, its easy derivatization, 10,11 and its remarkable redox properties, 3,12,13 endowing ferrocene and its derivatives numerous applications in a wide range of fields, including catalysis, 14 sensing, 15,16 batteries, 17 medicinal chemistry, [18][19][20] and teranostics. 21 Ferrocene has also been explored as an appealing building block in the construction of organometallic chromophores, including asymmetric multidentate ferrocene functionalized Schiff bases and their metal complexes, 22 with tunable and switchable properties relevant to a wide variety of materials-related applications.…”

Synthesis of long straight‐chain alkane substituted ferrocene with ultra‐robust oil solubility as multifunctional organometallic additive

“…The ferrocene's appealing sandwich structure allows other C-X bonds to easily substitute the C-H bond in cyclopentadienyl rings (where X = F, Cl, Br, B, P, Si, and so forth). 38 Among that, the Friedel-Crafts acylation is a high-efficient synthetic method for the synthesis of multi-functionalized ferrocene derivatives with the desired substituent groups. 39 As shown in Figure 1a, Lewis acid was used as a catalyst in the Friedel-Crafts acylation of ferrocene with myristyl chloride to create the new organometallic compound TFc.…”