Copper-Mediated Deconstructive Ring Cleavage of Cyclic Thioethers with Boron Compounds.

Area of Science:

• Organic Chemistry
• Synthetic Methodology

Background:

• Cyclic thioethers are important sulfur-containing compounds.
• Efficient methods for their deconstructive ring cleavage are valuable in organic synthesis.

Purpose of the Study:

• To develop a novel synthetic route for the deconstructive ring cleavage of cyclic thioethers.
• To explore the preparation of vinyl sulfides and functionalized linear sulfides.

Main Methods:

• Utilized a Chan-Lam type reaction involving boron compounds.
• Developed a sequential hydroboration/ring cleavage process starting from alkynes.

Main Results:

• Successfully achieved deconstructive ring cleavage of cyclic thioethers.
• Established a new route for preparing vinyl sulfides.
• Demonstrated the versatility of various nucleophiles to yield diverse functionalized sulfides.

Conclusions:

• The developed Chan-Lam type process offers an effective method for cyclic thioether ring opening.
• The sequential hydroboration/ring cleavage provides a versatile approach to vinyl and linear sulfides.