Novel Stereoselective Phase Transfer Catalytic Synthesis and Some Applications of ( E )-2-Chlorovinylthioarenes and Hetarenes

Abstract

A novel two-step method for the preparation of ( E )-2-chlorovinylthioarenes (or hetarenes) from thiols and 1,1,2-trichloroethane in the phase transfer catalytic systems solid K 2 CO 3 /solid KI/18-crown-6/xylene and solid KOH/18-crown-6/toluene has been developed. ( E )-2-chlorovinylthioarenes were isolated in yields up to 98%. Utilization of ( E )-2-chlorovinylthioarenes in the Heck and Stille reactions has been shown.

Keywords:

• Chlorovinylthioarenes
• Heck Reaction
• Phase Transfer Catalytic System
• Stille Reaction