Hydrogen Atom Transfer-Mediated Cyclisations of Nitriles

Area of Science:

• Organic Chemistry
• Catalysis
• Synthetic Methodology

Background:

• Intramolecular C-C coupling reactions are crucial for synthesizing cyclic compounds.
• Developing new synthetic strategies for ketone formation remains an active area of research.

Purpose of the Study:

• To describe a new hydrogen atom transfer-mediated intramolecular C-C coupling reaction.
• To establish a novel bond disconnection strategy for ring-closing reactions.
• To synthesize ketones via imine intermediates.

Main Methods:

• Utilizing phenylsilane (PhSiH3) as the hydrogen atom source.
• Employing iron(III) acetylacetonate [Fe(acac)3] as a catalyst.
• Investigating the reaction between alkenes and nitriles.

Main Results:

• Successful intramolecular C-C bond formation between alkenes and nitriles.
• Formation of cyclic ketones through imine intermediates.
• Demonstrated scope including sterically hindered ketones, spirocycles, and fused cyclic systems.

Conclusions:

• The developed method offers a new strategic approach for constructing cyclic ketones.
• The reaction is versatile and applicable to diverse substrates, including sterically demanding ones.
• This work expands the toolkit for synthesizing complex organic molecules.