The Application of [Bis(trifluoroacetoxy)iodo]benzene (PIFA) in the Synthesis of Nitrogen-Containing Heterocycles

Direct oxidation of suitably functionalized amides by application of the hypervalent iodine reagent PIFA [bis(trifluoroacet­oxy)iodo]benzene allows straightforward access to a variety of nitrogen-containing heterocycles. Comprehensive results from our group on the scope and limitations of such transformations will be highlighted. 1 Introduction 2 PIFA-Mediated Electrophilic Aromatic Amidation 3 PIFA-Mediated Olefin Amidation 4 PIFA-Mediated Alkyne Amidation 5 PIFA-Mediated Alkyne N–N and N–S Bond Formation 6 Synthetic Applications of PIFA-Mediated Heterocyclization Reactions 6.1 Synthesis of Pyrazoloquinolinones 6.2 Synthesis of Pyrrolobenzodiazepine DC-81 ( 17 ) 6.3 Synthesis of Pyrrolobenzodiazepines 71 and 77 6.4 Formal Synthesis of (±)-Clausenamide 6.5 Synthesis of Polyhydroxylated Indolizidines 7 Conclusions