Palladium‐Catalyzed Suzuki Coupling with Terminal Alkynes – Application to the Synthesis of 2,3‐Disubstituted Benzo[<i>b</i>]furans

Abstract

Abstract The Suzuki coupling reaction between alkynylboronic esters (generated in situ from acetylenic derivatives) and aryl bromides, pyridyl bromides or vinyl bromides is reported. 5‐ endo ‐ dig ‐iodocyclisation of o ‐alkynylanisoles, generated by this palladium‐catalyzed Suzuki coupling reaction, was performed with N ‐iodosuccinimide (NIS) in the presence of BCl 3 . 2‐Substituted 3‐iodobenzo[ b ]furans were synthesized and transformed into 2,3‐disubstituted benzo[ b ]furans by Suzuki coupling reactions in high yields. (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2005)