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An Economical Access to 3,4-Diaryl-2(5H)-furanones and 4-Aryl-6-methyl-2(2H)-pyranones by Pd-Catalyzed Suzuki-Type Arylation of 3-Aryl-4-tosyloxy-2(5H)-furanones and 6-Methyl-4-tosyloxy-2(2H)-pyranones, Respectively

✍ Scribed by Fabio Bellina; Chiara Marchetti; Renzo Rossi

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
153 KB
Volume
2009
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

Both symmetrical and unsymmetrical 3,4‐diaryl‐substituted 2(5__H__)‐furanones have been efficiently synthesized using an inexpensive procedure involving the Pd(OAc)~2~/PCy~3~‐catalyzed Suzuki‐type arylation of readily available 3‐aryl‐4‐tosyloxy‐2(5__H__)‐furanones as the key step. The mild conditions of this arylation protocol have also been used for the high yielding synthesis of 4‐aryl‐6‐methyl‐2(2__H__)‐pyranones from 6‐methyl‐4‐tosyloxy‐2(2__H__)‐pyranone. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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## Abstract 3,4‐Dichloro‐2(5__H__)‐furanone, which has been prepared efficiently from mucochloric acid, has been transformed selectively into 4‐aryl‐3‐chloro‐2(5__H__)‐furanones either by Suzuki‐ or Stille‐type reactions. These monochloro derivatives have been used as precursors either to (__Z__)‐4