An Interrupted Pummerer/Nickel-Catalysed Cross-Coupling Sequence.

Area of Science:

• Organic Chemistry
• Synthetic Methodology
• Catalysis

Background:

• The synthesis of functionalized styrenes is crucial for various chemical applications.
• Existing methods may lack efficiency, require harsh conditions, or use expensive reagents.
• Development of streamlined and versatile synthetic routes is an ongoing area of research.

Purpose of the Study:

• To develop an operationally simple and efficient method for styrene elaboration.
• To utilize a nickel-catalyzed cross-coupling strategy involving sulfonium salt intermediates.
• To accommodate diverse organozinc coupling partners for broad applicability.

Main Methods:

• Development of an interrupted Pummerer reaction followed by nickel-catalyzed cross-coupling.
• One-pot procedure utilizing commercially available sulfoxides, catalysts, and ligands.
• Application of sp-, sp2-, and sp3-hybridized organozinc reagents.

Main Results:

• Successful synthesis of functionalized styrenes in high yields over two steps.
• Direct formation of stable alkenyl sulfonium salt intermediates.
• Demonstration of compatibility with a wide range of organozinc coupling partners.
• Interrupted Pummerer/cyclisation approach enabled access to carbo- and heterocyclic alkenyl sulfonium salts.

Conclusions:

• The developed interrupted Pummerer/nickel-catalyzed cross-coupling strategy offers a robust and efficient route to functionalized styrenes.
• The method's operational simplicity, mild conditions, and substrate scope make it a valuable tool in organic synthesis.
• The strategy provides access to novel alkenyl sulfonium salts for further cross-coupling applications.