Palladium-catalyzed alkoxycarbonylation of allylic natural terpenic functionalized olefins

Houssame, Soufiane El; Firdoussi, Larbi El; Allaoud, S.; Karim, Abdellah; Castanet, Yves; Mortreux, André

doi:10.1016/s1381-1169(00)00381-2

Cited by 25 publications

(17 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…15 CeCl 3 or InCl 3 combined with NaOCl have been reported as efficient systems for allylic chlorination of terminal olefins. [12][13][14][15][16] In line with our continuous interest in the functionalization of natural terpenic olefins, [5][6][7] we report here the result of our investigation on the allylic chlorination using a combination of sodium hypochlorite and molybdenum pentachloride.…”

Section: Introductionmentioning

confidence: 99%

“…[1][2][3][4] Previously, we have reported that allylic amines, alcohols, ketones and alkoxycarbonyl derivatives can be obtained in good yields by the metal complex catalyzed amination, oxidation and alkoxycarbonylation of some monoterpenes. [5][6][7] Chlorination represents a valuable pathway to produce versatile starting materials that are widely used in synthetic organic chemistry. [8][9][10][11] Chloride compounds can be prepared directly by bubbling molecular chlorine, but the difficulty of handling chlorine gas limits this procedure.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Allylic chlorination of terpenic olefins using a combination of MoCl5 and NaOCl

Boualy¹,

Firdoussi²,

Ali³

et al. 2011

J. Braz. Chem. Soc.

Self Cite

View full text Add to dashboard Cite

MoCl 5 é usado como eficiente agente na cloração alílica de olefinas terpênicas na presença de NaOCl como doador de cloro. Vários terpenóides são convertidos aos cloretos de alila correspondentes em moderados a bons rendimentos em condições reacionais brandas e otimizadas. Diferentes precursores de molibdênio são estudados. Dentre eles, MoO 3 fornece bom rendimento, mas depois de um tempo de reação maior.MoCl 5 is applied as efficient agent in allylic chlorination of terpenic olefins in the presence of NaOCl as chlorine donor. Various terpenes are converted to the corresponding allylic chlorides in moderate to good yield under mild and optimized reaction conditions. Different molybdenum precursors are also studied. Among them, MoO 3 gives good yield, but after a longer reaction time.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Allylic chlorination of terpenic olefins using a combination of MoCl5 and NaOCl

Boualy¹,

Firdoussi²,

Ali³

et al. 2011

J. Braz. Chem. Soc.

Self Cite

View full text Add to dashboard Cite

show abstract

“…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

Self Cite

View full text Add to dashboard Cite

“…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%