Introduction of Allyl and Prenyl Side-Chains in Aromatic Systems via Suzuki Cross-Coupling Reactions

DARÍO C. GERBINO; SANDRA D. MANDOLESI; JULIO C. PODESTÁ; HANS G. SCHMALZ

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Wiley-VCH Verlag GmbH & Co. KgaA

Lugar: Weinheim, Germany; Año: 2009 vol. 23 p. 3964 - 3972

1434-193X

This paper reports some studies aiming at the developement of a general protocol useful for the synthesis of allyl- and prenylaromatic compounds. The first part deals with the preparation of boron reagents like arylboronic acids and their pinacol esters as well as of pinacol allyl- and prenylboronates. The second part of the paper is devoted to the use of these boron reagents in Suzuki–Miyaura cross-coupling reactions leading to allylation and prenylation of aromatic compounds. Of the six methods studied, the most promising results were obtained by using the Pd2(dba)3-catalyzed reactions of arylboronic acids with allyl and prenyl bromides, that lead to the products of cross coupling in high yields (average 87%), and the reactions of aryl trifluoroborates with allyl and prenyl bromides catalyzed by Pd(OAc)2 that lead to the products of  coupling in all cases in high yields (average 82%).