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Title: New reactive sites enabled via an allyl-to-allyl 1,4-Rh(III) migration
Author: Korkis, Stamatis E.
ISNI:       0000 0004 7228 5228
Awarding Body: University of Nottingham
Current Institution: University of Nottingham
Date of Award: 2018
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The Rh(III)-catalysed oxidative C–H allylation and homoallylation of N-acetylbenzamides with 1,3-dienes is described. The presence of allylic hydrogens cis to the less substituted alkene of the 1,3-diene is important for the success of these reactions, though not essential. With the assistance of reactions using deuterated 1,3-dienes, a proposed mechanism is provided. The key step is postulated to be the first reported examples of allyl-to-allyl 1,4-Rh(III) migration. Importantly, migration to primary or secondary allylic position results in allylation products, whereas migration to a tertiary position leads to homoallylation. Using 1,4-dienes as the coupling partner, N-tosylbenzamides are homoallylated. Preliminary results indicate a mixture of isomer products, with major isomer resulting from an allyl-to-allyl 1,4-Rh(III) migration.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: QD241 Organic chemistry