Selective palladium-catalysed functionalization of limonene: synthetic and mechanistic aspects

Firdoussi, Larbi El; Baqqa, Ahmed; Allaoud, S.; Allal, Badia Ait; Karim, Abdallah; Castanet, Yves; Mortreux, André

doi:10.1016/s1381-1169(97)00285-9

Cited by 55 publications

(28 citation statements)

References 25 publications

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“…The first is Wacker oxidation process using PdCl 2 /CuCl 2 /O 2 in glacial acetic acid [27][28][29][30][31]. Carveyl acetates, carveol, and carvone are among the major products.…”

Section: Introductionmentioning

confidence: 99%

Iron(II, III)-Catalyzed Oxidation of Limonene by Dioxygen

2007

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Labile iron(II) and iron(III) complexes {[Fe II (bpy) 2 2+ ] solv and [Fe III (bpy) 2 3+] solv } in acetonitrile activate dioxygen for the oxidation of limonene to produce mainly carvone, carveol, limonene oxide, and perillaldehyde. Iron(III) complex is reduced by the substrate to iron(II) one, which activates dioxygen. Probably the catalyst interacts with substrate prior to the oxidation process. Perillaldehyde is likely formed directly from oxidation of methyl group (not via alcohol). However, the aldehyde is also reduced to perillyl alcohol by the reduced form of the catalyst.

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“…The first is Wacker oxidation process using PdCl 2 /CuCl 2 /O 2 in glacial acetic acid [27][28][29][30][31]. Carveyl acetates, carveol, and carvone are among the major products.…”

Section: Introductionmentioning

confidence: 99%

Iron(II, III)-Catalyzed Oxidation of Limonene by Dioxygen

2007

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“…The previous work we undertook on the oxidation of terpenic substrates catalyzed by palladium, allowed us to establish unambiguously the importance of the π-allyl intermediate species to control the regio-and stereoselectivity of these reactions [3,4]. As part of studies on these intermediates in monoterpenic [4] and sesquiterpene series [5][6][7][8], we report here on the complex bis(jr-allylvalencene)-dichlorodipalladium. We have established the regiochemistry of the title complex using NMR and 13 C NMR sperctroscopy.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of bis(д-allylvalencene)dichlorodipalladium, [PdCl(C15H23)]2

Farrouji¹,

Firdoussi²,

Ali³

et al. 2009

Zeitschrift Für Kristallographie - New Crystal Structures

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“…The previous work we undertook on the oxidation of terpenic substrates catalyzed by palladium, allowed us to establish unambiguously the importance of the p-allyl intermediate species to control the regio-and stereoselectivity of these reactions [3,4]. As part of studies on these intermediates in monoterpenic [4] and sesquiterpenic series [5][6][7][8], we report here on the complex bis(p-allylvalencene)-dichlorodipalladium. We have established the regiochemistry of the title complex using 1 HNMR and 13 CNMR sperctroscopy.…”

Section: Discussionmentioning

confidence: 99%