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Synlett 2004(13): 2351-2354  
DOI: 10.1055/s-2004-832845
LETTER
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Homocoupling of Arylboronic Acids and Esters Using Fluoride in Aqueous Solvents

Sreenivas Punna, David D. Díaz, M. G. Finn*
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 N. Torrey Pines Rd., La Jolla, CA 92037, USA
Fax: +1(858)7848850; e-Mail: mgfinn@scripps.edu;
Further Information

Publication History

Received 14 April 2004
Publication Date:
24 September 2004 (online)

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Abstract

Homocoupling of both arylboronic acids and esters has been found to proceed using catalytic amounts of PdII and stoichiometric amounts of TBAF under air atmosphere at room temperature, offering a mild and efficient protocol for the synthesis of symmetrical biaryls via C(sp 2)-C(sp 2) bond formation. Aryl boronic acids bearing bromide substitution form polyphenylenes.

Key words

boronic acids - palladium - fluoride - biaryls - water

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Water may simply assist the substitution steps, although dissociation of chloride from Pd(PPh3)2Cl2 was not detected by NMR in D2O in the absence of boron component.