Direct Access to Fully Substituted 3‐Formyl‐4‐iodofurans through Iodocyclization of α‐Alkynyl β‐Alkoxy Enones. Issue 1 (12th November 2012)

• Record Type: Journal Article
• Authors: Raffa, Guillaume; Balme, Geneviève; Monteiro, Nuno
• Is Part Of: European journal of organic chemistry. Issue 1(2013)
• Page Start: 105
• Page End: 110
• Publication Date: 2012-11-12
• Subjects: Synthetic methods -- Homogeneous catalysis -- Cross‐coupling -- Cycli­zation -- Oxygen heterocycles -- Alkynes; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201201203
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A facile access to 3‐formyl‐4‐iodofurans is presented. This protocol consists of a Sonogashira cross‐coupling of an α‐iodo β‐alkoxy enone with a terminal alkyne and the subsequent iodonium‐promoted heteroannulation–dealkoxylation of the resulting α‐alkynyl β‐alkoxy enone by treatment with N ‐iodosuccinimide in aqueous medium. Abstract : Fully substituted 3‐formyl‐4‐iodofurans are easily accessible under mild reaction conditions from readily available α‐iodo β‐alkoxy enones and terminal alkynes. The proposed two‐step protocol combines a Sonogashira cross‐coupling reaction and subsequent iodocyclization without the need to isolate the intermediate α‐alkynyl β‐alkoxy enone.