N-heterocyclic carbenes. IV.1synthesis of symmetrical and unsymmetrical imidazolium salts with abietane moiety

✍ Scribed by V. A. Glushkov; K. A. Arapov; M. S. Kotelev; K. S. Rudowsky; K. Yu. Suponitsky; A. A. Gorbunov; O. A. Maiorova; P. A. Slepukhin

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 224 KB
• Volume: 23
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.20745

✦ Synopsis

Abstract

Methyl 12‐chloromethyl‐dehydroabie‐tate reacts with 1‐benzyl‐ and 1‐arylimidazoles to give unsymmetrically substituted imidazolium chlorides (1a–i), with abietane moiety. Starting from methyl 12‐aminodehydroabietate, symmetrically substituted diterpene‐based salts of imidazolinium (4) and imidazolium (5) were synthesized. Anion exchange afforded corresponding (1e·BF~4~) and (1e·PF~6~). The new compounds were tested as ligands for a Pd‐catalyzed Suzuki‐Miyaura reaction. The molecular structure of (1e) is reported. © 2011 Wiley Periodicals, Inc. Heteroatom Chem 23:5–15, 2012; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20745