The iodoarylation reaction of heteroatom-tethered omega-arylalkynes offers an efficient and straightforward entry to heterocycles. As a result, both C-C ring-closing from readily available precursors, and concomitant selective iodination take place. The first related study conducted in water is presented.
An efficient protocol to synthesize iodohydrins from alkenes is presented. Reactions were conducted in aqueous media using safe and readily available sodium iodide (the most abundant form of the element), and a highly convenient oxidant such as hydrogen peroxide. Addition of a protic acid triggers a faster and efficient process, a role formally related to that played by haloperoxidase enzymes in naturally occurring transformations. The successful application of these conditions to multigram scale preparations and over natural products derivatives is also discussed.
Using water as the reaction medium, ketones can be transformed into alpha-iodoketones upon treatment with sodium iodide, hydrogen peroxide and an acid; interestingly, alpha-iodoketones can be also obtained from secondary alcohols through a metal-free tandem oxidation-iodination approach.
Ring closure reactions O 0130Intramolecular Iodoarylation Reaction of Alkynes: Easy Access to Derivatives of Benzofused Heterocycles. -The title reaction results in C-C ring closure of readily available precursors and concomitant selective iodination. Furthermore, the first related study conducted in water is described. Derivative (IIb) is used for further elaboration by consecutive Pd-catalyzed cross-coupling reactions. -(BARLUENGA*, J.; TRINCADO, M.; MARCO-ARIAS, M.; BALLESTEROS, A.; RUBIO, E.; GONZALEZ, J. M.; Chem. Commun. (Cambridge) 2005, 15, 2008-2010; Inst. Quim. Organomet. "Enrique Moles", Univ. Oviedo, E-33071 Oviedo, Spain; Eng.) -M. Paetzel 36-036
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