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Synlett 2012(3): 478-479  
DOI: 10.1055/s-0031-1290133
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© Georg Thieme Verlag Stuttgart ˙ New York

Diaryliodonium(III) Salts: Arylating Agents

Nobutaka Yamaoka*
College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan
e-Mail: rc011058@ed.ritsumei.ac.jp;
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Publication History

Publication Date:
25 January 2012 (online)

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Introduction

Diaryliodonium(III) salts, ArI+Ar′X- (Ar, Ar′ = aryl), are classically known as trivalent iodine species with two aryl ligands bound to an iodine atom. These are readily available and easy-to-handle compounds, and typically form stable crystals. The salts tend to convert into more stable monovalent iodoarenes under reductive conditions. Due to the good leaving ability of the iodoarene groups, they are used as arylating reagents in various reactions, for example, nucleophilic substitution reactions with various nucleophiles, such as organometallic agents, enolates, [¹] and heteroatom nucleophiles, [²] and coupling reactions using transition-metal catalysts. [³] They are also valuable as benzyne precursors. [4] Recently, a number of new C-H bond arylations for providing biaryls have been reported. [5] In specific cases, they serve as unique arylating agents under metal-free conditions. [6]

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