Dimerisation des α-cyanoesters par le diacetate d'iodosobenzene.

Seveno, Anne; Morel, G.; Foucaud, A.; Marchand, Evelyne

doi:10.1016/s0040-4039(01)83236-6

Cited by 22 publications

(1 citation statement)

References 15 publications

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“…The (diacetoxyiodo) benzene derivatives probably operate in the same manner as the iodosylbenzenes. In this connection it should be noted that the acetoxy groups are readily displaced by water or methanol (Seveno et al, 1977). (Dinitratoiodo) benzenes undergo rapid hydrolysis in water and (dinitratoiodo)-2-nitrobenzene may therefore be assumed to coordinate as 2-nitroiodosylbenzene.…”

Section: Discussionmentioning

confidence: 99%

Iodosylbenzene derivatives as oxygen donors in cytochrome P-450 catalyzed steroid hydroxylations

Gustafsson

Rondahl²,

Bergman³

1979

Biochemistry

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The mechanism of cytochrome P-450 catalyzed steroid hydroxylations in rat liver microsomes has been investigated by employing derivatives of iodosylbenzene as oxygen donors. The model steroid substrate androstenedione which was hydroxylated in positions 7 alpha, 6 beta, and 16 alpha was used in reactions supported by NADPH, iodosylbenzene, and iodosylbenzene derivatives. Evidence for cytochrome P-450 involvement in iodosylbenzene-sustained androstenedione hydroxylation included inhibition by substrates and modifiers of cytochrome P-450. The most efficient oxygen donors were (diacetoxyiodo)-2-nitrobenzene greater than (diacetoxyiodo)-2-chlorobenzene greater than 2-nitroiodosylbenzene greater than (dinitratoiodo)-2-nitrobenzene greater than (diacetoxyiodo)benzene greater than (diacetoxyiodo)-2-methoxybenzene greater than 4-(diacetoxyiodo)toluene greater than iodosylbenzene. The capacity of the oxidation agents to serve as oxygen donors in cytochrome P-450 dependent steroid hydroxylation is probably dependent upon several factors such as the tendency of iodosyl compounds to associate, which decreases coordination with the heme iron, the presence of bulky substituents in the 2 position (decreases association), and the presence of electron-withdrawing substituents (tends to decrease coordination with the heme iron). The rates of 7 alpha, 6 beta, and i6 alpha hydroxylation of androstenedione catalyzed by (diacetoxyiodo)-2-nitrobenzene were 108-, 130-, and 167-fold higher, respectively, than the rates of the NADPH-supported reactions. These results strongly suggest that the rate-limiting step in NADPH-sustained cytochrome P-450 catalyzed reactions is the rate of reduction of cytochrome P-450.

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Section: Discussionmentioning

confidence: 99%

Iodosylbenzene derivatives as oxygen donors in cytochrome P-450 catalyzed steroid hydroxylations

Gustafsson

Rondahl²,

Bergman³

1979

Biochemistry

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Destruction and Construction: Application of Dearomatization Strategy in Aromatic Carbon–Nitrogen Bond Functionalization

Wang

et al. 2015

Angewandte Chemie

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The formation of carbon–carbon bonds through the functionalization of aromatic carbon–nitrogen bonds is a highly attractive synthetic strategy in the synthesis of aromatic molecules. In this paper, we report a novel aromatic carbon–nitrogen bond functionalization reaction by using a simple dearomatization strategy. Through this process para‐substituted anilines serve as a potential aryl source in the construction of a range of functionalized aromatic molecules, such as quaternary carbon centers, α‐keto esters, and aldehydes.

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Destruction and Construction: Application of Dearomatization Strategy in Aromatic Carbon–Nitrogen Bond Functionalization

Wang

et al. 2015

Angew Chem Int Ed

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The formation of carbon-carbon bonds through the functionalization of aromatic carbon-nitrogen bonds is a highly attractive synthetic strategy in the synthesis of aromatic molecules. In this paper, we report a novel aromatic carbon-nitrogen bond functionalization reaction by using a simple dearomatization strategy. Through this process para-substituted anilines serve as a potential aryl source in the construction of a range of functionalized aromatic molecules, such as quaternary carbon centers, α-keto esters, and aldehydes.

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Dimerisation des α-cyanoesters par le diacetate d'iodosobenzene.

Cited by 22 publications

References 15 publications

Iodosylbenzene derivatives as oxygen donors in cytochrome P-450 catalyzed steroid hydroxylations

Iodosylbenzene derivatives as oxygen donors in cytochrome P-450 catalyzed steroid hydroxylations

Destruction and Construction: Application of Dearomatization Strategy in Aromatic Carbon–Nitrogen Bond Functionalization

Destruction and Construction: Application of Dearomatization Strategy in Aromatic Carbon–Nitrogen Bond Functionalization

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