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20.5.5.1.2.2 Variation 2: Using (Diacyliodo)arenes

DOI: 10.1055/sos-SD-020-00983

Nelson, S. G.Science of Synthesis, (2007201049.

Putative iodonium benzoate salts and their derived alkynyl esters can also be accessed by a route that does not require prior formation of alkynyliodonium ions. Specifically, (dibenzoxyiodo)benzene (8) reacts with lithium acetylides to afford alkynyl benzoates 10 in 2757% yields (Scheme 4).[‌8‌] The reaction probably proceeds through lithium acetylide mediated benzoate substitution at the trivalent iodine center to deliver the trivalent iodine carboxylate species 9, which is analogous to the intermediate derived from preformed alkynyliodonium ions. The structural diversity available in acetylide anion precursors (terminal alkynes) and the aryl residue in the (diaroyloxyiodo)arene salts means that this procedure provides access to a wider range of alkynyl alkanoates than are available via preformed alkynyliodonium ions. Alkynyl acetates can also be prepared by this procedure by using (diacetoxyiodo)benzene, but products are generally less stable than the benzoate analogues and their isolated chemical yields are therefore commensurately lower (225%).

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