Eco-friendly Oxidative Iodination of Various Arenes with Sodium Percarbonate as the Oxidant？.docVIP

Molecules 2005, 10, 1307–1317 molecules ISSN 1420-3049 Eco-friendly Oxidative Iodination of Various Arenes with Sodium Percarbonate as the Oxidant? Agnieszka Zielinska and Lech Skulski* Chair and Laboratory of Organic Chemistry, Faculty of Pharmacy, Medical University, 1 Banacha Street, 02 – 097 Warsaw, Poland. ? Preliminary results were presented at the Eighth Electronic Conference on Synthetic Organic Chemistry (ECSOC-8, /ecsoc-8), November 1-30, 2004 (paper A022) * To whom the correspondence should be addressed; E-mail: lechskulski@; Tel./Fax: +(48) 22 5720643 Received: 17 May 2005; in revised form: 12 July 2005 / Accepted: 13 July 2005 / Published: 31 October 2005 Abstract: Six easy laboratory procedures are presented for the oxidative iodination of various aromatics, mostly arenes, with either molecular iodine or potassium iodide (used as the sources of iodinating species, I+ or I3+), in the presence of sodium percarbonate (SPC), a stable, cheap, easy to handle, and eco-friendly commercial oxidant. Keywords: Iodoarenes, arenes, iodine, sodium iodide, sodium percarbonate as oxidant Introduction Aromatic iodides are generally more reactive, albeit are more costly, than the respective bromides and chlorides. There are many different methods, direct and indirect, for their synthesis [1], and they are widely used in organic synthesis in chemical laboratories and, to a lesser extent, in industry. Moreover, they are able to form a variety of aromatic hypervalent iodine derivatives, which have found increasing applications in modern organic synthesis [2]. Our two latest reviews [3, 4] relate and explain a variety of direct oxidative iodination methods, suitable for both activated and deactivated aromatics, mostly arenes, devised in our laboratory since 1990, as well as our novel methods for preparing several classes of aromatic hypervalent iodine compounds, easily a