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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Pd-catalyzed intermolecular C-H amination with alkylamines
Eun Jeong Yoo1, Sandy Ma, Tian-Sheng Mei
1Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Journal of the American Chemical Society
|April 28, 2011
Summary
This study presents a new catalytic method for synthesizing arylalkyl amines. It utilizes palladium catalysts for C-H amination, offering a direct route from benzoic acids to valuable amine products.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- C-H amination is a crucial transformation in organic synthesis.
- Developing efficient catalytic systems for amine synthesis remains an active research area.
- Direct functionalization of C-H bonds offers atom-economical synthetic pathways.
Purpose of the Study:
- To develop a novel catalytic C-H amination of N-aryl benzamides.
- To explore the use of O-benzoyl hydroxylamines as aminating agents.
- To establish a one-pot procedure for synthesizing secondary and tertiary arylalkyl amines.
Main Methods:
- Palladium(II) and Palladium(0) catalyzed C-H amination reactions.
- Utilizing O-benzoyl hydroxylamines as key reagents.
- A one-pot procedure involving in situ generation of O-benzoyl hydroxylamines from secondary amines and benzoyl peroxide.
Main Results:
- Successful C-H amination of N-aryl benzamides was achieved using Pd catalysts.
- A one-pot method was developed using secondary amines and benzoyl peroxide.
- The reaction provides a convergent synthesis of tertiary and secondary arylalkyl amines.
Conclusions:
- A new catalytic disconnection for arylalkyl amine synthesis has been established.
- The developed methodology offers a versatile route from benzoic acids to valuable amine products.
- This work expands the toolkit for constructing complex amine structures.
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Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
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