Stereoselective Cross-Coupling of Baylis–Hillman Acetates with Diphenyl Disulfides and Diselenides Using Palladium Acetate

Abstract

An efficient method is described for the stereoselective synthesis of diorganyl chalcogenides from a variety of Baylis–Hillman acetates and diaryl chalcogens using palladium catalyst. This reaction is a convenient new method to produce unsymmetrical sulfides and selenides in good yields.

Keywords:

• Baylis–Hillman acetates
• diaryl chalcogens
• stereoselective cross-coupling
• thioethers

ACKNOWLEDGMENTS

P. S. R. and M. A. R. thank the Council of Scientific and Industrial Research (CSIR), India, for the award of senior research fellowships.

Notes

Note. Reactions conditions: 1 (1 mmol), 1 (0.6 mmol), Pd catalyst (2 mol%), PPh₃ (10 mol%), and solvent (3 ml) at rt for 12 h.

^a Reaction conditions: Baylis–Hillman acetate (1.0 mmol), diaryl disulfide (0.6 mmol), Pd(OAc)₂ (2 mol%), PPh₃ (10 mol%) in methanol (3 mL) at rt.

^b Products with (Z)-stereoselectivity.

^c Isolated yields.

^d Product with (E)-stereoselectivity.