New Synthesis of Furans: the Rhodium-Catalysed Carbonylative Addition of Arylboronic Acids to Propargylic Alcohols/ Cyclisation Sequence

✍ Scribed by Julien Dheur; Mathieu Sauthier; Yves Castanet; André Mortreux

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 208 KB
• Volume: 352
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/adsc.200900683

✦ Synopsis

Abstract

The rhodium‐catalysed carbonylative addition of arylboronic acids to propargylic alcohols yields gamma‐hydroxy enones that are readily cyclised through a dehydration step to the corresponding furan analogues. The transformation was improved thanks to the screening of the reaction conditions and consequent improvements were obtained from the use of dicarbonylrhodium iodide [Rh(CO)~2~I]~2~ as catalyst precursor. The generalisation of the reaction was then further investigated by employing variously substituted arylboronic acids and propargylic alcohols.