Yodación de alcanos y reacciones de yodofuncionalización de ureas, alenos y eninos

Abstract

The work presented in this Thesis describes new synthetic methodology promoted by iodinating reagents, to prepare iodinated alkanes, carbon-heteroatom and carbon-carbon bond forming reactions with ureas, allenes and enynes. Chapter 1 focusses on the iodination of saturated hydrocarbons promoted by a mixture of hypervalent iodine compounds and elementary iodine. This activation of C-H bonds is a selective process that occurs under thermal conditions. Chapter 2, divided in three sections, is devoted to the study of the reactivity of bis(pyridine) iodonium tetrafluoroborate reagent (IPy2BF4) towards the functionalization of unsaturated systems. This reagent is an easy and useful alternative to the use of transition metals in these processes. The first part is related to the study of the oxidative intramolecular diamination of alkenes with tethered ureas. The second section reports the results of direct inter and intramolecular 2-iodoallylation of arenes with allenes. This approach makes possible the preparation of some yet unknown basic scaffolds such as 2-iodo-1,4-dihydronaphthalenes. The last part deals with the reactivity of 1,6-enynes with IPy2BF4. The use of this reagent allows the synthesis of five, six and seven member rings depending on the substituents of the starting material.