| Summary: | A new PdII-catalysed interrupted oxidative-Mizoroki-Heck reaction has been developed. This reaction enables the synthesis of a wide range of polyheterocycles in a single step starting with simple substrates and involves the addition of a tethered diene unit across two joined heterocycles. The reaction has proven to be general for dienes tethered to indoles and pyrroles (in blue) and for 1t-allylcapturing heterocycles such as furan, thiophene and pyrrole (in red). In some cases the non-oxidized variant can be obtained through careful choice of oxidant and reaction conditions The scope and mechanism of this reaction have been explored leading to the proposed mechanism shown below. C-H activation of the first, tethered, heterocycle (in this case pyrrole), leads to migratory insertion of the pendant alkene and rapid capture of the π-allyl system by the second heterocycle (in this case furan). Initial products show complete diastereoselectivity and in some cases can be isolated, or oxidized in situ to fully aromatic systems
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