Functionalization of aromatic and heterocyclic systems. Regioselective introduction of 2-oxoalkyl chain or cyano functions via organoiron complexes

Sutherland, R. G.; Chowdhury, Ratan; Piórko, Adam; Lee, Choi Chuck

doi:10.1021/jo00229a038

Cited by 36 publications

(13 citation statements)

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“…For synthesis of related compounds refer to Lee, Gill, Iqbal, Azogu & Sutherland (1982) and Sutherland, Pi6rko, Chowdbury & Lee (1987). For structOrally similar compounds refer to Abboud, Simonsen, Pi6rko & Sutherland (1990, 1991, Sutherland, Pi6rko, Lee, Simonsen & Lynch (1988), Lynch, Thomas, Simonsen, Pi6ko & Sutherland (1986) and Simonsen, Lynch, Sutherland & Pi6rko (1985).…”

Section: Bond Lengths (A) and Angles (°)mentioning

confidence: 99%

Structure of (η5-cyclopentadienyl)(η6-p-isopropylnitrobenzene)iron(II) trifluoroacetate at 198 K

Abboud¹,

Simonsen²,

Piórko³

et al. 1991

Acta Crystallogr C

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Section: Bond Lengths (A) and Angles (°)mentioning

confidence: 99%

Structure of (η5-cyclopentadienyl)(η6-p-isopropylnitrobenzene)iron(II) trifluoroacetate at 198 K

Abboud¹,

Simonsen²,

Piórko³

et al. 1991

Acta Crystallogr C

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“…Reactive nucleophiles such as cyanide, hydride [123], methyl-, and phenyl lithium [2] add to unactivated (arene)FeCp + complexes, whereas less reactive nucleophiles such as phenyl acetylide, lithium salts of acetonitrile, nitromethane and ketones [84,124] require an electron-withdrawing group to be present on the arene ring of the complex. On the other hand, cyanide or an anion derived from propionitrile added to several unactivated arene complexes [67,76,[123][124][125][126].…”

Section: Addition/oxidation With (Arene)fecp Cation Complexesmentioning

confidence: 99%

(Arene)Cr(CO)3 Complexes: Aromatic Nucleophilic Substitution

Semmelhack

Chlenov

2004

Topics in Organometallic Chemistry

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Transition metals coordinated to the pi system of arenes function as strong electronwithdrawing groups and favor nucleophilic addition to the arene to give cyclohexadienyl-metal complexes. The regioselectivity of addition is influenced in subtle and indirect ways, compared to the powerful effect on both reactivity and regioselectivity of electron-withdrawing groups attached to the sigma bond system of the arene. The intermediate cyclohexadienyl complexes can be processed in several ways, leading to several distinct synthesis methods. Useful reactivity is known for several metal systems and each is discussed for specific reaction types. The presence of a fluoro or chloro substituent on the arene allows an effective analog of classical S N Ar reactivity, with a wide range of nucleophiles including simple amines, alkoxides, and carbon anions. Another general process is the addition/protonation protocol, where a hydrogen substituent on the arene is replaced by a nucleophile. This opens new questions of regioselectivity since the typical arene ligand has several hydrogens which are candidates for substitution. The formation of five-and six-membered rings by both general mechanisms are known. Less general indirect mechanisms (e.g., tele substitution) have also been defined.

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“…High yields of tropylium (eq 8) and triphenylcyclopropenyl (eq 9) cations have been isolated in the presence of acids such as perchloric, phosphoric, and picric acid, 23 and oxonium, 24 thioxonium, 23,25 and pyridinium 23,26 salts may be prepared in reasonable yields from appropriate starting materials under essentially similar conditions. In addition to the key reactions above, DDQ has been used for the oxidative removal of chromium, 62 iron, 63 and manganese 64 from their complexes with arenes and for the oxidative formation of imidazoles and thiadiazoles from acyclic precursors. Dehydrogenation of Carbonyl Compounds.…”

Section: Introductionmentioning

confidence: 99%