Download PDF
Synfacts 2006(8): 0859-0859  
DOI: 10.1055/s-2006-941992
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Ferrocene-Based Bisphosphine Ligands for Ni-Catalyzed Cross-Coupling Reactions

Contributor(s): Yasuhiro Uozumi, Tsutomu Kimura
Y. Lu, E. Plocher, Q.-S. Hu*
College of Staten Island, New York and the City University of New York, USA
Further Information

Publication History

Publication Date:
21 July 2006 (online)

    Permissions and Reprints

Significance

Polymer-supported ferrocene-based bisphosphines 1a and 1b were prepared and used as ligands in nickel(0)-catalyzed cross-coupling reactions. The polymer-supported bisphosphines 1 were prepared from ferrocene in three steps; addition of lithiated ferrocene to aldehydes, Suzuki coupling polymerization of the diols 2 with diboronic acid, and phosphinylation of the polymeric diols 3 with HPPh2 (eq. 1). The Suzuki coupling of aryl chlorides with aryl boronic acids proceeded in the presence of Ni(cod)2 and bisphosphines 1 to give the biaryls in 60-99% yield (eq. 2). The Kumada coupling of aryl fluorides with Grignard reagents took place in the presence of Ni(acac)2 and bisphosphines 1 to give the biaryls in 53-77% yield (eq. 3).