Copper-Catalyzed Cross-Coupling of Thiols with 1-Iodo-2-chalcogenoalkenes

✍ Scribed by Flávia Manarin; Juliano A. Roehrs; Ethel A. Wilhelm; Gilson Zeni

• Publisher: John Wiley and Sons
• Year: 2008
• Tongue: English
• Weight: 173 KB
• Volume: 2008
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200800495

✦ Synopsis

Abstract

We describe herein a new method for the synthesis of densely substituted alkenes containing chalcogenide atoms by a cross‐coupling reaction between 1‐iodo‐2‐chalcogenoalkenes and thiols using copper(I) as catalyst in a ligand‐free system. The desired cross‐coupling products were obtained in good yields and with satisfactory selectivity. The developed protocol tolerates a wide range of functional groups; the reactions of alkyl‐, benzyl‐, and arylthiols with neutral, electron‐deficient, and electron‐rich substituents on the aromatic ring were explored in the absence of any supplementary additives. In addition, the reaction proceeded cleanly under mild reaction conditions and was sensitive to the nature of the catalyst, base, and solvent.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)