Anode-induced arylthiol-amine cross-coupling: A nontraditional strategy to access sulfinamides

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Electrosynthesis

Background:

• Sulfinamides are vital structural motifs in natural products and biologically active molecules.
• Current synthetic routes for sulfinamides are often inefficient, requiring difficult precursor preparation and harsh conditions, limiting their broad applicability.

Purpose of the Study:

• To develop a streamlined and efficient electrocatalytic strategy for the direct synthesis of sulfinamides.
• To overcome the limitations of traditional sulfinamide synthesis methods.

Main Methods:

• An intermolecular oxidative cross-coupling reaction between readily available arylthiols and aliphatic amines was employed.
• Electrocatalysis was utilized to facilitate the S─N bond formation under mild conditions.

Main Results:

• The developed electrocatalytic strategy provides a practical and efficient route to sulfinamides.
• Mechanistic studies revealed that four sequential oxidations at the anode are key to radical generation and S─N bond formation.

Conclusions:

• This work presents a significant advancement in sulfinamide synthesis, offering a versatile and economical alternative.
• The electrocatalytic approach broadens the synthetic scope and accessibility of sulfinamide compounds.