A general and efficient method for the palladium-catalyzed cross-coupling of thiols and secondary phosphines
Miki Murata and Stephen L. Buchwald*
*Department of Chemistry, Massachusetts Institute of Technology, 77
Massachusetts Ave. Bldg 18-305, Cambridge, MA 02139, USA, Email:
sbuchwal
mit.edu
M. Murata, S. L. Buchwald, Tetrahedron, 2004, 60, 7397-7403.
DOI: 10.1016/j.tet.2004.05.044
Abstract
A versatile and efficient Pd(OAc)2/1,1'-bis(diisopropylphosphino)ferrocene-catalyzed cross-coupling of thiols with aryl halides was developed. Aryl bromides and chlorides can be coupled to aliphatic and aromatic thiols - the widest substrate scope of any reported to date. This catalyst system also enables the coupling of secondary phosphines with aryl halides.
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Details
The document discusses a general and efficient method for the palladium-catalyzed cross-coupling of thiols and secondary phosphines with aryl halides, developed by Miki Murata and Stephen L. Buchwald at MIT. The catalyst system used is Pd(OAc)2/1,10-bis(diisopropylphosphino)ferrocene (DiPPF), which has a broad substrate scope, including various aryl bromides and chlorides that can be coupled with aliphatic and aromatic thiols. This method overcomes limitations of previous systems and is the most general system available to date. The catalyst system also enables the coupling of secondary phosphines with aryl bromides and chlorides. The study highlights the importance of using suitable ligands and bases to achieve high yields and efficient reactions. The document provides detailed experimental procedures and results, demonstrating the effectiveness of the Pd(OAc)2/DiPPF catalyst system in forming carbon-sulfur and carbon-phosphorus bonds. The research was supported by the National Institutes of Health and various pharmaceutical companies. The findings contribute significantly to the field of organic chemistry, offering a versatile and reliable method for synthesizing aryl sulfides and tertiary phosphines.
Key Words
Palladium catalysis, Thiol cross-coupling, Phosphine cross-coupling
ID: J72-Y2004-690
