Suzuki–Miyaura arylations of tetramic acid sulfonates: Evaluation of lactam protection, sulfonate esters, and sterics

✍ Scribed by Sarah J. P. Yoon-Miller; Kathryn M. Dorward; Kimberly P. White; Erin T. Pelkey

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2009
• Tongue: English
• Weight: 194 KB
• Volume: 46
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.96

✦ Synopsis

Abstract

magnified image

The synthesis of 3,4‐diaryl‐3‐pyrrolin‐2‐ones and 4‐aryl‐3‐pyrrolin‐2‐ones using Suzuki–Miyaura cross‐coupling reactions of tetramic acid sulfonates with arylboronic acids has been studied. The effect that sulfonate ester, sterics, and lactam protection has on the cross‐coupling reaction was evaluated. As expected, triflates were better cross‐coupling partners than the corresponding tosylates. The yields were only partially affected by the incorporation of aryl groups at the 3‐position. Importantly, tetramic acid triflates (and to a lesser extent tosylates) lacking a lactam protecting group were still competent substrates. J. Heterocyclic Chem., 46, 447 (2009).