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Primary amines can be protected as benzophenone imines, and the protected amines are stable in flash chromatography. [7] Buchwald-Hartwig amination involves coupling aromatic halide and amine to form carbon-nitrogen bonds with the help of palladium-based catalysts. Benzophenone imine can be used as an ammonia-equivalent in such reactions. [1]
Several strategies have been developed to overcome this based on reagents that serve as ammonia equivalents. The use of a benzophenone imine or silylamide can overcome this limitation, with subsequent hydrolysis furnishing the primary aniline. [37] [38] [39]
The general structure of an imine. In organic chemistry, an imine (/ ɪ ˈ m iː n / or / ˈ ɪ m ɪ n /) is a functional group or organic compound containing a carbon–nitrogen double bond (C=N).
First, the nickel metal dehydrogenates the alcohol to form a ketone and Ni-H complex. Then, the ketone reacts with ammonia to form an imine. Finally, the imine reacts with Ni-H to regenerate catalyst and form primary amine. An example of a homogeneous catalytic system is the reductive amination of ketones done with an iridium catalyst. [20]
Benzophenone is a naturally occurring organic compound with the formula (C 6 H 5) 2 CO, generally abbreviated Ph 2 CO. Benzophenone has been found in some fungi, fruits and plants, including grapes. [4] It is a white solid with a low melting point and rose-like odor [5] that is soluble in organic solvents. Benzophenone is the simplest ...
The Leuckart reaction is the chemical reaction that converts aldehydes or ketones to amines.The reaction is an example of reductive amination. [1] The reaction, named after Rudolf Leuckart, uses either ammonium formate or formamide as the nitrogen donor and reducing agent.
The reaction is generally performed in an aqueous solution at close to boiling. The first methylation of the amine begins with imine formation with formaldehyde. The formic acid acts as a source of hydride and reduces the imine to a secondary amine. Loss of carbon dioxide gas renders the reaction irreversible. Despite being more hindered, the ...
In organic chemistry, the Mannich reaction is a three-component organic reaction that involves the amino alkylation of an acidic proton next to a carbonyl (C=O) functional group by formaldehyde (H−CHO) and a primary or secondary amine (−NH 2) or ammonia (NH 3). [1] The final product is a β-amino-carbonyl compound also known as a Mannich base.