Download PDF
Synfacts 2006(11): 1163-1163  
DOI: 10.1055/s-2006-949484
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Pd-Catalyzed Synthesis of Phenols and Aromatic Ethers from Aryl Halides

Contributor(s): Paul Knochel, Andrei Gavryushin
K. W. Anderson, T. Ikawa, R. E. Tundel, S. L. Buchwald*
Massachusetts Institute of Technology, Cambridge, USA
Further Information

Publication History

Publication Date:
24 October 2006 (online)

    Permissions and Reprints

Significance

While a broad number of Pd-catalyzed carbon-heteroatom bond formation reactions are known up to date, this is the first report for a direct preparation of phenols from aryl halides and OH- as a nucleophile. This method allows an easy conversion of various aryl and hetero­aryl chlorides and bromides into the corresponding phenols in high yields. Very good functional-group compatibility is observed, despite the highly basic conditions. The prepared phenols can be converted in situ into alkylaryl ethers, using the same Pd catalyst and the corresponding alkyl halide. The method allows also an easy preparation of substituted benzofuranes.