Easy Preparation of [Bis(trifluoroacetoxy)iodo]arenes from Iodoarenes, with Sodium Percarbonate as the Oxidant.docVIP

Molecules 2002, 7, 810-812 molecules ISSN 1420-3049 Easy Preparation of [Bis(trifluoroacetoxy)iodo]arenes from Iodoarenes, with Sodium Percarbonate as the Oxidant? Pawel Kazmierczak and Lech Skulski* Chair and Laboratory of Organic Chemistry, Faculty of Pharmacy, Medical University, PL 02-097, 1 Banacha Street, Warsaw, Poland. ? This short paper was presented at the Sixth Electronic Conference on Synthetic Organic Chemistry (ECSOC-6, /ecsoc-6), September 1-30, 2002 (paper A007). * To whom correspondence should be addressed. E-mail: lskulski@.pl; Tel/Fax: +(48) 22 5720643 Received: 15 October 2002; in revised form: 21 October 2002 / Accepted: 21 October 2002 / Published: 30 November 2002 Abstract: Easy and effective preparations of the nearly pure [bis(trifluoroacetoxy)- iodo]arenes, ArI(OCOCF)3, from some iodoarenes, ArI, are reported, using an anhydrous sodium percarbonate/(CF3CO)2O/CH2Cl2 system. The colorless, freshly prepared ArI(OCOCF3)2 thus obtained were 98-99% pure (by iodometry). Keywords: [Bis(trifluoroacetoxy)iodo]arenes from iodoarenes, sodium percarbonate as oxidant Introduction [Bis(trifluoroacetoxy)iodo]arenes, ArI(OCOCF3)2, are potent and selective oxidants, widely used in modern organic synthesis. So far, they have been synthesized from either ArI, or ArIO, or ArICl2, or directly from ArH, but the most common method depends on their preparation (in moderate yields) from the corresponding (diacetoxyiodo)arenes, ArI(OAc)2, by their recrystallization from CF3COOH [1, 2].  Molecules 2002, 7 811 Results and Discussion Recently, in our laboratory we have devised a simple, easy, and efficient method for the direct preparation of ArI(OCOCF3)2 from the respective iodoarenes, ArI, in a binary anhydrous solvent system, (CF3CO)2O/CH2Cl2, using commercially available sodium percarbonate, 2Na2CO3. 3H2O2, as the oxidant (Scheme 1 and Table 1): Scheme 1 (CF3CO)2O/CH2Cl2 3ArI(OCOCF