Twofold Ferrocene C–H Lithiations For One-Step Difunctionalizations

Erb, William; Mongin, Florence

doi:10.1055/s-0037-1610396

Cited by 12 publications

(5 citation statements)

References 74 publications

(78 reference statements)

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“…Compound 11 is one of the product tetraiodoferrocenes obtained in the ortho -lithiation reaction of 1,1′-diiiodoferrocene followed by reaction with iodine. This is formed because of the iodine scrambling process (halogen dance) recently described by Mongin and co-workers …”

Section: Resultsmentioning

confidence: 99%

Synthetic Route to 1,1′,2,2′-Tetraiodoferrocene That Avoids Isomerization and the Electrochemistry of Some Tetrahaloferrocenes

et al. 2021

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An efficient synthesis of 1,1′,2,2′-tetraiodoferrocene is described that uses 1,1′,2,2′-tetrakis(tri-n-butylstannyl)ferrocene as a key intermediate in its synthesis. In an attempt to examine the stepwise mechanism, the reaction of the tetratin-substituted ferrocene 1,1′,2,2′-tetrakis(tri-n-butylstannyl)ferrocene with iodine was monitored by 1H NMR and a series of coexisting intermediate compounds such as 1,1′-bis(tri-n-butylstannyl)-2,2′-diodoferrocene were observed. The crystal structure of 1,1′,2,2′-tetraiodoferrocene has been determined, and it is compared with the structure of the previously reported 1,1′,2,2′-tetrabromoferrocene and 1,2,4,1′-tetraiodoferrocene. The comparative electrochemistry of 1,1′,2,2′-tetrachloroferrocene, 1,1′,2,2′-tetrabromoferrocene, and 1,1′,2,2′-tetraiodoferrocene is described. The crystal structure of 1,2,1′-triiodoferrocene is also reported for comparative use to illustrate the scope of the synthetic method.

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Section: Resultsmentioning

confidence: 99%

Synthetic Route to 1,1′,2,2′-Tetraiodoferrocene That Avoids Isomerization and the Electrochemistry of Some Tetrahaloferrocenes

et al. 2021

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“…Ferrocene is a three-dimensional electron-rich organometallic aromatic compound, which was discovered almost 70 years ago. [9,10] The chemistry of ferrocene has been the subject of continuing research under various aspects, [11][12][13][14][15][16][17][18] such as stereoselective catalysis, [19][20][21][22][23][24] redox chemistry, [25] CÀ H activation, [26][27][28][29] materials chemistry, [30][31][32][33][34][35][36][37][38][39] bioorganic and medicinal chemistry. [30,[40][41][42][43][44][45][46][47][48][49] The facile rotation of the cyclopentadienyl ligands renders ferrocene moieties in many derivatives conformationally flexible.…”

Section: Introductionmentioning

confidence: 99%

New π‐Extended 1,1′‐Disubstituted Ferrocenes with Thioate and Dithioate End Groups

Schmiel

Butenschön

2021

Eur J Org Chem

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Extended π systems based on 1,1′‐aryl or (2‐arylethynyl) disubstitution at ferrocene with thioate or dithioate end groups are reported. In the context of molecular electronics, such end groups are possible alternative end groups for the attachment of molecular wires at gold surfaces. The respective thioates were successfully prepared in high yields via the respective carboxylic acid derivatives. Subsequent treatment with Lawesson's reagent led to the respective dithioates. However, this did not work in the presence of triple bonds, in these cases, product mixtures were formed. On the basis of literature evidence with Woollin's reagent, the selenium analog of Lawesson's reagent, one product was tentatively characterized as a double cyclization product of two triple bonds and two molecules of Lawesson's reagent. Preliminary experiments towards the formation of gold complexes by reaction with a Johnphos gold(I) salt are included.

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“…Since the discovery of ferrocene, 1,2 many mono, 1,2-and 1,1′-disubstituted derivatives have been synthesized. [17][18][19][20][21][22][23] However, other substitution patterns and more substituted derivatives have been significantly less studied. [17][18][19][20][21][22]24,25 Among the highly substituted ferrocenes already described, those containing five identical substituents on the same cyclopendadienyl (e.g.…”

Section: Introductionmentioning

confidence: 99%

From ferrocene to decasubstituted enantiopure ferrocene-1,1′-disulfoxide derivatives

et al. 2023

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Twofold Ferrocene C–H Lithiations For One-Step Difunctionalizations

Abstract: For some aromatics, a twofold C-H deprotolithiation can be achieved, allowing these compounds to be subsequently difunctionalized in one step. This short review brings together examples in which ferrocenes are converted in this way.

Cited by 12 publications

References 74 publications

Synthetic Route to 1,1′,2,2′-Tetraiodoferrocene That Avoids Isomerization and the Electrochemistry of Some Tetrahaloferrocenes

Synthetic Route to 1,1′,2,2′-Tetraiodoferrocene That Avoids Isomerization and the Electrochemistry of Some Tetrahaloferrocenes

New π‐Extended 1,1′‐Disubstituted Ferrocenes with Thioate and Dithioate End Groups

From ferrocene to decasubstituted enantiopure ferrocene-1,1′-disulfoxide derivatives

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