Allylic amination of unfunctionalyzed olefins by nitroarenes and CO, catalyzed by Ru3(CO)12/Ph-BIAN (Ph-BIAN=bis(phenylimino)acenaphthenequinone): extension to the synthesis of allylic amines with strongly electron-withdrawing or electron-donating groups on the aryl ring

Tetrahedron ◽  
2004 ◽  
Vol 60 (23) ◽  
pp. 4989-4994 ◽  
Author(s):  
Fabio Ragaini ◽  
Sergio Cenini ◽  
Fabrizio Turra ◽  
Alessandro Caselli
Keyword(s):  
Allylic Amines ◽  
Allylic Amination ◽  
Aryl Ring ◽  
Electron Donating Groups

Regioselective Synthesis of Optically Active Trifluoromethyl Group Substituted Allylic Amines by Palladium-Catalyzed Allylic Amination

Synlett ◽  
2010 ◽  
Vol 2010 (19) ◽  
pp. 2887-2890 ◽  
Author(s):  
Motoi Kawatsura ◽  
Toshiyuki Itoh ◽  
Takuya Hirakawa ◽  
Kazunori Ikeda ◽  
Hiroshi Ogasa
Keyword(s):  
Optically Active ◽  
Regioselective Synthesis ◽  
Trifluoromethyl Group ◽  
Allylic Amines ◽  
Allylic Amination ◽  
Palladium Catalyzed

Regioselective synthesis of trifluoromethyl group substituted allylic amines via palladium-catalyzed allylic amination

2008 ◽  
Vol 49 (15) ◽  
pp. 2450-2453 ◽  
Author(s):  
Motoi Kawatsura ◽  
Takuya Hirakawa ◽  
Tomoko Tanaka ◽  
Daiji Ikeda ◽  
Shuichi Hayase ◽  
...  
Keyword(s):  
Regioselective Synthesis ◽  
Trifluoromethyl Group ◽  
Allylic Amines ◽  
Allylic Amination ◽  
Palladium Catalyzed

Relative migratory aptitudes in the Schmidt reaction of arylpropanones and 2-arylcyclohexanones

1978 ◽  
Vol 31 (9) ◽  
pp. 1989 ◽  
Author(s):  
RH Prager ◽  
JM Tippett ◽  
AD Ward
Keyword(s):  
Charge Transfer ◽  
Aromatic Ring ◽  
Low Temperatures ◽  
Hydrazoic Acid ◽  
Schmidt Reaction ◽  
Aryl Ring ◽  
Charge Transfer Interaction ◽  
Alkyl Groups ◽  
A Charge ◽  
Electron Donating Groups

The relative migratory aptitude of benzyl and alkyl groups in the reaction of arylpropanones and 2-arylcyclohexanones with hydrazoic acid depends on the solvent, temperature and nature of the substituents in the aryl ring. It is suggested that at low temperatures electron- donating groups in the aromatic ring favour a charge-transfer interaction which affects the relative migratory aptitudes.

ChemInform Abstract: Regioselective Synthesis of Trifluoromethyl Group Containing Allylic Amines by Palladium-Catalyzed Allylic Amination and Sequential Isomerization.

ChemInform ◽  
2012 ◽  
Vol 43 (12) ◽  
pp. no-no
Author(s):  
Takuya Hirakawa ◽  
Kazunori Ikeda ◽  
Daiji Ikeda ◽  
Tomoko Tanaka ◽  
Hiroshi Ogasa ◽  
...  
Keyword(s):  
Regioselective Synthesis ◽  
Trifluoromethyl Group ◽  
Allylic Amines ◽  
Allylic Amination ◽  
Palladium Catalyzed

scholarly journals Site-Selective Allylic C-H Amination with Aliphatic Amines

2021 ◽  
Author(s):  
Shengchun Wang ◽  
Yiming Gao ◽  
Demin Ren ◽  
He Sun ◽  
Linbin Niu ◽  
...  
Keyword(s):  
Hydrogen Atom ◽  
Building Blocks ◽  
Hydrogen Atom Transfer ◽  
Allylic Amines ◽  
Allylic Amination ◽  
Alkyl Amines ◽  
Reaction Proceeds ◽  
Bond Options ◽  
A Site ◽  
Site Selective

Abstract The direct coupling of olefins and alkyl amines represents the most efficient and atom-economical approach to prepare aliphatic allylamines which are fundamental building blocks. However, the method that achieves this goal while exhibiting exquisite control over the site at which the amine is introduced remains elusive. Herein, we report that the combination of a photocatalyst and a cobaloxime enables site-selective allylic C–H amination of olefins with secondary alkyl amines to afford allylic amines, eliminating the need for oxidants. This reaction proceeds by a radical-based mechanism distinct from those of existing allylic amination reactions. It affords the product resulting from cleavage of the stronger, primary allylic C–H bonds over other weaker allylic C–H bond options. DFT calculations reveal that this selectivity originates from a cobaloxime-promoted hydrogen atom transfer (HAT) process. Our method is compatible with a broad scope of alkenes, and can be extended to achieve a site- and diastereoselective amination of natural terpenes.

Organocatalytic Allylic Amination of Morita–Baylis–Hillman Carbonates­

Synthesis ◽  
2018 ◽  
Vol 51 (04) ◽  
pp. 907-920 ◽  
Author(s):  
Jan Veselý ◽  
Bedřich Formánek ◽  
Michal Šimek ◽  
Martin Kamlar ◽  
Ivana Císařová
Keyword(s):  
Building Block ◽  
Aromatic Amines ◽  
Optical Purity ◽  
Optically Active ◽  
Allylic Amines ◽  
Allylic Amination ◽  
Cholesterol Lowering ◽  
High Optical Purity ◽  
Efficient Route ◽  
Lowering Drug

An organocatalytic asymmetric allylic amination of Morita–Baylis–Hillman carbonates with aromatic amines in the presence of β-isocupreidine is described. Chiral allylic amines were obtained in almost quantitative yields (90–96%) with moderate enantioselectivity. Recrystallization afforded products in good yields (45–73%) and high optical purity (82–99% ee). This method provides a facile and efficient route to obtain optically active β-lactams, including the building block of the cholesterol-lowering drug Ezetimibe.

scholarly journals Enantioselective construction of C-chiral allylic sulfilimines via the iridium-catalyzed allylic amination with S,S-diphenylsulfilimine: asymmetric synthesis of primary allylic amines

2015 ◽  
Vol 6 (1) ◽  
pp. 777-781 ◽  
Author(s):  
Rebecca L. Grange ◽  
Elizabeth A. Clizbe ◽  
Emma J. Counsell ◽  
P. Andrew Evans
Keyword(s):  
Asymmetric Synthesis ◽  
Allylic Amines ◽  
Allylic Amination ◽  
Amination Reaction

We have devised a highly regio- and enantioselective iridium-catalyzed allylic amination reaction with the sulfur-stabilized aza-ylide, S,S-diphenylsulfilimine.

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