Bifunctionalization of α-Bromophenone: An Access to Functionalized β-Keto Thiosulfones

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Sulfur Chemistry

Background:

• Thiosulfonates are versatile sulfur-containing compounds.
• Efficient synthesis of β-keto sulfides is crucial for various applications.
• Existing methods may lack generality or require harsh conditions.

Purpose of the Study:

• To develop a simple and high-yielding method for synthesizing β-keto sulfides.
• To explore the use of asymmetrical and symmetrical thiosulfonates in this transformation.
• To investigate the scope and limitations of the reaction with various substituted ketones.

Main Methods:

• Reaction of thiosulfonates (both symmetrical and asymmetrical) with ketones.
• Utilizing mild reaction conditions.
• Purification and characterization of the resulting β-keto thiosulfones.

Main Results:

• Successful synthesis of a variety of β-keto thiosulfones (α-thioaryl-β-keto sulfones).
• Moderate to high yields were obtained for diverse substituted compounds.
• The reaction demonstrated reliability and efficiency at the gram-scale.
• Electron-donating and electron-withdrawing substituents on the substrates were well-tolerated.

Conclusions:

• A practical and efficient strategy for β-keto sulfide synthesis has been established.
• The method offers a valuable tool for accessing diverse α-thioaryl-β-keto sulfones.
• The proposed protocol is suitable for gram-scale synthesis, highlighting its potential utility.