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Title: The formation of polyheterocycles via palladium-catalysed C-H activation
Author: Cooper, Stephen P.
ISNI:       0000 0004 5923 2236
Awarding Body: University of Bristol
Current Institution: University of Bristol
Date of Award: 2015
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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
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available