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

Abstract

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

Key words

heterocycles - hypervalent iodine - olefin amidation - alkyne amidation - aromatic amidation

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