Recent Progress in Arylation Reactions with Diaryliodonium Salts

Hypervalent iodine compounds have attracted much attention in organic syntheses due to their characteristics of low toxicity, mild conditions, and high selectivity as efficient reagents in many organic transformations [1]. The application of high-valent iodine compounds has been summarized in many books and reviews [2]. They are always used as efficient alternatives to heavy metal-based oxidants and expensive organometallic catalysts. Diaryliodonium salts (DAIS), as a class of hypervalent iodine (III) compounds, have been used as valid electrophilic arylation reagents because of their attributes, such as having solid-state, excellent stability to air and moisture, and good leaving group property [3-6]. They are suitable for the acquisition of a variety of target compounds under metal or metal-free catalysis. Such arylation reagents have relatively high reactivity and good selectivity in many transformations, and the reaction conditions are generally very mild; thus, diaryliodonium salts are regarded as new generation arylation reagents. The chemistry of DAIS, including their structural characteristics, has been widely reported and reviewed in previous literature several years ago [7, 12]. Based on our research work about DAIS, in this review, the structure and preparation methods of DAIS are introduced briefly, and the organic synthetic utilities and the key ABSTRACT In recent years, diaryliodonium salts have been extensively exploited as green, efficient electrophilic arylation reagents in a large range of organic synthesis. These arylating reagents exhibit relatively high reactivity and good selectivity in many transformations. In this review, the synthetic methods towards diaryliodonium salts are described briefly, and the research progress in arylation reactions by using diaryliodoniums in C-C and carbonheteroatom bond formation, especially in enantioselective C-C bond formation and cascade reactions, in recent ten years is summarized and discussed in detail.

Automated summary

Hypervalent iodine compounds, in particular diaryliodonium salts, have been widely used in organic synthesis due to their low toxicity, mild conditions, and high selectivity. These compounds serve as efficient alternatives to heavy metal-based oxidants and expensive organometallic catalysts, showing good reactivity and selectivity in various transformations.