Selective synthesis of acylated caprolactam via sequential Michael addition/palladium-catalyzed alpha-arylation of ketones

2021 ◽  
Author(s):  
Xin-Xing Wu ◽  
Hao Ye ◽  
Ming Li ◽  
Jianing Qian ◽  
Hong Dai ◽  
...  
Keyword(s):  
Michael Addition ◽  
Bond Formation ◽  
Selective Synthesis ◽  
Methyl Ketones ◽  
Rapid Access ◽  
Palladium Catalyzed ◽  
Efficient Route

A formal [6 + 1] annulation reaction provides an efficient route enabling rapid access to diverse caprolactams by the double C–C bond formation of the same site from methyl ketones.

One-pot three-component selective synthesis of isoindolo[2,1-a]quinazoline derivatives via a palladium-catalyzed cascade cyclocondensation/cyclocarbonylation sequence

2017 ◽  
Vol 15 (17) ◽  
pp. 3674-3680 ◽  
Author(s):  
Shenghai Guo ◽  
Jianhui Zhai ◽  
Fang Wang ◽  
Xuesen Fan
Keyword(s):  
Selective Synthesis ◽  
One Pot ◽  
Palladium Catalyzed ◽  
Efficient Route ◽  
Quinazoline Derivatives

An efficient route to 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-diones via Pd-catalyzed carbonylative cyclization of 2-aminobenzamides with 2-bromobenzaldehydes and CO is reported.

Ligand-Enabled γ-C(sp3)–H Olefination of Free Carboxylic Acids

2020 ◽  
Author(s):  
Kiron Kumar Ghosh ◽  
Alexander Uttry ◽  
Francesca Ghiringhelli ◽  
Arup Mondal ◽  
Manuel van Gemmeren
Keyword(s):  
Reaction Mechanism ◽  
Carboxylic Acids ◽  
Michael Addition ◽  
Kinetic Studies ◽  
Wide Range ◽  
Palladium Catalyzed

We report the ligand enabled C(sp3)–H activation/olefination of free carboxylic acids in the γ-position. Through an intramolecular Michael-addition, δ-lactones are obtained as products. Two distinct ligand classes are identified that enable the challenging palladium-catalyzed activation of free carboxylic acids in the γ-position. The developed protocol features a wide range of acid substrates and olefin reaction partners and is shown to be applicable on a preparatively useful scale. Insights into the underlying reaction mechanism obtained through kinetic studies are reported.<br>

Direct and Selective Synthesis of Adipic and Other Dicarboxylic Acids by Palladium‐Catalyzed Carbonylation of Allylic Alcohols

2020 ◽  
Vol 59 (46) ◽  
pp. 20394-20398
Author(s):  
Ji Yang ◽  
Jiawang Liu ◽  
Yao Ge ◽  
Weiheng Huang ◽  
Helfried Neumann ◽  
...  
Keyword(s):  
Dicarboxylic Acids ◽  
Allylic Alcohols ◽  
Selective Synthesis ◽  
Palladium Catalyzed

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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