Visible-Light-Induced FeCl₃-Promoted Dehydroxypropylative Selenylation of Acyclic Alcohols

Area of Science:

• Organic Chemistry
• Photochemistry
• Catalysis

Background:

• Developing efficient methods for synthesizing unsymmetrical monoselenides is crucial in organic chemistry.
• Traditional methods often require harsh conditions or specialized reagents.

Purpose of the Study:

• To develop a novel, visible-light-promoted protocol for the dehydroxypropylative selenylation of tertiary acyclic alcohols.
• To achieve direct C-C bond cleavage and C-Se bond formation without additional photocatalysts.

Main Methods:

• Utilizing iron(III) chloride (FeCl3) as a promoter under visible light irradiation.
• Reacting tertiary acyclic alcohols with various diselenides.
• Employing mechanistic studies to elucidate the reaction pathway.

Main Results:

• Successful synthesis of unsymmetrical monoselenides via C-C bond cleavage and C-Se bond formation.
• The protocol demonstrates a broad substrate scope with diverse alcohols and diselenides.
• The reaction is scalable to gram-scale synthesis, indicating practical applicability.

Conclusions:

• The developed FeCl3-promoted visible-light reaction provides an efficient route to unsymmetrical monoselenides.
• The reaction proceeds via a radical pathway initiated by ligand-to-metal charge transfer (LMCT).
• This method offers a sustainable and practical approach for constructing valuable organoselenium compounds.