UC Pd: A New Form of Pd/C for Sonogashira Couplings

✍ Scribed by Christophe Duplais; Arnold J. Forman; Benjamin A. Baker; Bruce H. Lipshutz

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 422 KB
• Volume: 16
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.200902471

✦ Synopsis

Abstract

Screening of different sources of Pd/C shows reagents of highly variable nanoparticle sizes and oxidation states of the metal. Typically, catalysts with higher surface area are viewed as likely to be the more reactive. In this paper a new form of Pd/C, “UC Pd” is described that is shown to contain larger nanoparticles yet it is the most reactive catalyst of those sold commercially for Sonogashira coupling reactions. UC Pd functions efficiently in the absence of a copper co‐catalyst, under very mild and “green” conditions using inexpensive 95 % EtOH at 50 °C. It is also the only form of Pd/C that can be recycled. In side‐by‐side reactions with several commercially available forms of Pd/C, none compete successfully with UC Pd under standardized conditions. Physical data obtained from extensive surface analysis using TEM, XRD, XPS, and CO‐TPD measurements lead to an explanation behind the unique reactivity of this new recyclable form of Pd/C.