Gold‐Catalyzed Intramolecular Carbothiolation of Alkynes: Synthesis of 2,3‐Disubstituted Benzothiophenes from (α<i>‐</i>Alkoxy Alkyl) (<i>ortho</i>‐Alkynyl Phenyl) Sulfides

Abstract

Gold forms rings: AuCl-catalyzed cyclization of (α-alkoxy alkyl) (ortho-alkynyl phenyl) sulfides 1 proceeds under mild conditions to give 3-(α-alkoxy alkyl) benzothiophenes 2 in high yields for a wide range of substrates (see scheme). The starting materials are readily available through acetalization of ortho-bromobenzenethiol and subsequent Sonogashira coupling. This methodology provides an atom-economic route to sulfur-containing heteroarenes. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2006/z601178_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.