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DEDICATED CLUSTER FULL PAPERS DOI: 10.1002/adsc.200700373 Efficient and General One-Pot Synthesis of Diaryliodoniu Triflates: Optimization, Scope and Limitations a a a, Marcin Bielawski, Mingzhao Zhu, and Berit Olofsson * a Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden Phone: (+ 46)-8-6747264; fax: (+ 46)-8-154908; e-mail: berit@organ.su.se Received: July 27, 2007; Published online: November 27, 2007 This paper is dedicated to Professor Jan-Erling Bckvall on the occasion of his 60th birthday. Supporting information for this article is available on the WWW under http://asc.wiley-vch.de/home/. Abstract: Symmetrical and unsymmetrical diarylio- action has been extended to the direct synthesis of donium triflates have been synthesized from both symmetrical iodonium salts from iodine and arenes, electron-deficient and electron-rich arenes and aryl conveniently circumventing the need for aryl iodides. iodides with mCPBA and triflic acid. A thorough in- vestigation of the optimization, scope and limitations Keywords: arenes; aromatic substitution; diaryliodo- has resulted in an improved one-pot protocol that is nium salts; hypervalent compounds; iodine; oxida- fast, high-yielding, and operationally simple. The re- tion Introduction tions allows milder reaction conditions than in cou- plings with aryl halides.[7–9] Furthermore, diaryliodoni- Hypervalent iodine compounds have recently re- um salts are used to generate benzynes[10] and serve ceived co