Palladium-catalyzed decarboxylation-dehydrogenation of allyl .beta.-oxo carboxylates and allyl enol carbonates as a novel synthetic method for .alpha.-substituted .alpha.,.beta.-unsaturated ketones

1982 ◽  
Vol 104 (21) ◽  
pp. 5844-5846 ◽  
Author(s):  
Isao Shimizu ◽  
Jiro Tsuji
Keyword(s):  
Synthetic Method ◽  
Unsaturated Ketones ◽  
Palladium Catalyzed ◽  
Alpha Beta

scholarly journals Selective Synthesis of N-Acylnortropane Derivatives in Palladium-Catalysed Aminocarbonylation

Molecules ◽  
2021 ◽  
Vol 26 (6) ◽  
pp. 1813
Author(s):  
László Kollár ◽  
Ádám Erdélyi ◽  
Haroon Rasheed ◽  
Attila Takács
Keyword(s):  
Synthetic Method ◽  
Selective Synthesis ◽  
Varied Structure ◽  
Biological Importance ◽  
Aryl Iodides ◽  
Palladium Catalyzed ◽  
Derivatives Of

The aminocarbonylation of various alkenyl and (hetero)aryl iodides was carried out using tropane-based amines of biological importance, such as 8-azabicyclo[3.2.1]octan-3-one (nortropinone) and 3α-hydroxy-8-azabicyclo[3.2.1]octane (nortropine) as N-nucleophile. Using iodoalkenes, the two nucleophiles were selectively converted to the corresponding amide in the presence of Pd(OAc)2/2 PPh3 catalysts. In the presence of several iodo(hetero)arenes, the application of the bidentate Xantphos was necessary to produce the target compounds selectively. The new carboxamides of varied structure, formed in palladium-catalyzed aminocarbonylation reactions, were isolated and fully characterized. In this way, a novel synthetic method has been developed for the producing of N-acylnortropane derivatives of biological importance.

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