Phenyliodonium salts preparative methods

Because of the multitude and diversity of iodonium salts and zwitterions, some of which are labile or are prepared for specific purposes, their preparative methods are discussed in Chapter 8, for diaryl iodonium salts and related compounds, Chapter 9 for perfluoroalkyl, alkenyl and alkynyl phenyliodonium salts and Chapter 10 for zwitterionic iodonium compounds. In addition, the preparation of some lesser known reagents, including 2-iodosylbenzoic acid, is given in Chapter 12. 

Phenyliodonium Salts with an Aliphatic Moiety Preparative Methods. Reactivity of Perfluoroalkyl Phenyliodonium Salts. Reactivity of Other Iodonium Salts. 

Variations of this method permit the preparation of diverse salts, most of which are stable crystalline compounds. The group R in the alkynyl moiety can be of virtually any kind, for example aryl, aroyl, alkenyl, alkynyl, cyano, trimethylsilyl, etc. For some of these compounds only alkynylstannanes were suitable precursors, in combination with cyano phenyliodonium triflate double salts were also obtained in this way [10,11],... 

Using this method, several mesogen diacetylenes were obtained [49]. Palladium-catalysed coupling of an allylic cyclic carbonate with 1-pentynyl phenyliodonium tetrafluoroborate to give an enyne was highly successful [50]. Alkynyl iodonium triflates and lithium salts of diethyl 2-[(diphenylmethylene)amino]malonate were used for the preparation of alkynyl-a-amino acid derivatives, e.g. [51] ... 

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