Copper(I)-Catalyzed Synthesis of Ferrocenyl Aryl Ethers

Heiden, Markus R. an der; Frey, Guido D.; Plenio, Herbert

doi:10.1021/om0497893

Cited by 19 publications

(12 citation statements)

References 31 publications

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“…Many other studies on the formation of C(Ar)ÀO(phenol) bonds by using ligand-assisted methods are not discussed as they are outside the scope of this Minireview. [48]…”

Section: Coupling Reactions Of Aryl Halides With Phenolsmentioning

confidence: 99%

Catalytic CC, CN, and CO Ullmann‐Type Coupling Reactions

2009

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Copper-catalyzed Ullmann condensations are key reactions for the formation of carbon-heteroatom and carbon-carbon bonds in organic synthesis. These reactions can lead to structural moieties that are prevalent in building blocks of active molecules in the life sciences and in many material precursors. An increasing number of publications have appeared concerning Ullmann-type intermolecular reactions for the coupling of aryl and vinyl halides with N, O, and C nucleophiles, and this Minireview highlights recent and major developments in this topic since 2004.

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“…Many other studies on the formation of C(Ar)ÀO(phenol) bonds by using ligand-assisted methods are not discussed as they are outside the scope of this Minireview. [48]…”

Section: Coupling Reactions Of Aryl Halides With Phenolsmentioning

confidence: 99%

Catalytic CC, CN, and CO Ullmann‐Type Coupling Reactions

2009

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“…Furthermore, the study of electron transfer and electronic interactions within such structural motives has mainly been neglected 11. On the other hand, compounds in which two ferrocenyl termini are connected via a single atomic bridge, including C,16 N,17 O,18 Si,19,20 P,21 Hg,22 Sn,23 display interesting chemical and electrochemical properties. In addition, it has been demonstrated on the example of ferrocenyl functionalized pyrroles that the electronic characteristics of the bridge can be modified in a very controlled manner by electron‐withdrawing and electron‐donating functionalities at the nitrogen atom 24,25…”

Section: Introductionmentioning

confidence: 99%

Electronic Tuneable Dynamic and Electrochemical Behavior of N‐(Diferrocenylmethylene)anilines

Saloman

Hildebrandt

Korb

et al. 2015

Zeitschrift anorg allge chemie

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N-(Diferrocenylmethylene)anilines Fc 2 C=N-4-C 6 H 4 -R [3a R = CF 3 ; 3b R = Cl; 3c R = H; 3d R = CH 3 ; 3e R = OCH 3 ; Fc = Fe(η 5 -C 5 H 4 )(η 5 -C 5 H 5 )] with different electron-donating or -withdrawing functionalities were synthesized by a Schiff base reaction of substituted anilines H 2 N-4-C 6 H 4 -R (2a-2e) with diferrocenyl ketone (1). Within variable temperature NMR experiments activation enthalpies between 68.1 and 72.3 kJ·mol -1 for an E/Z exchange reaction of the imines were determined. It could be shown that the inversion barrier depends on the nature of the substituent R. Furthermore, electrochemical measurements were performed, demonstrating that the ferrocenyl units are oxidized separately. The electron density at the nitrogen

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“…The use of aryl difluorides allowed the synthesis of the first double ferrocenyloxy‐substituted aryl ethers of structural type H (Figure ) . This extended the reaction scope for the synthesis of ferrocenyl aryl ethers that were heretofore accessible by CuI‐mediated Ullmann couplings, one example of an intramolecular ring closing reaction and a few examples for S N Ar reactions involving quinolones …”

Section: Introductionmentioning

confidence: 95%