A Convenient Preparative Method for New 1,3-Bis(hetaryl)-2-chloropropen-1-ones Using β-Alkoxy-α-chloroalkenyllithium Compounds

✍ Scribed by Akinori Itoh; Miho Sakai; Mitsuhiro Yoshimatsu

• Publisher: John Wiley and Sons
• Year: 2007
• Tongue: English
• Weight: 178 KB
• Volume: 2007
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200600957

✦ Synopsis

Abstract

The 1,3‐biaryl and 1,3‐bis(hetaryl)propen‐1‐ones 14a–e, 16, 17a–c, 19, 20a and the corresponding acetals 15a–d, 18a and 21a–d were successfully synthesized by a stepwise process: the reaction of α‐chloro‐β‐ethoxyethenyllithium compounds and aldehydes and ketones, and the successive hydration with TMSOTf. Further palladium‐catalyzed arylation of 1,3‐biaryl‐2‐chloroprop‐2‐enones proceeded with good yields.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)