Copper-catalyzed cross-coupling of α-seleno-acylzirconocene chloride with haloalkynes: Synthesis of α-seleno-substituted vinyl alkynyl ketones

✍ Scribed by Ai-Ming Sun; Xian Huang

• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: English
• Weight: 139 KB
• Volume: 11
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/(sici)1098-1071(2000)11:2<91::aid-hc2>3.0.co;2-#

✦ Synopsis

The copper-catalyzed cross-coupling reaction of ␣-selenoacylzirconocene chloride 3 with haloalkynes in the presence of carbon monoxide gives ␣seleno-substituted vinyl alkynyl ketones 5 in moderate yields. The reaction conditions are neutral and mild enough (room temperature, 1 atm carbon monoxide) that other functional groups in either coupling partner can be brought unaltered into the coupled product. The E geometry in the ␣-alkylseleno vinylzirconocene reagent is maintained during the coupling reaction.