Regioselective magnesiation of N-heterocyclic molecules: securing insecure cyclic anions by a β-diketiminate-magnesium clamp

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Davin, Laia and McLellan, Ross and Hernán-Gómez, Alberto and Clegg, Bill and Kennedy, A R and Stepek, Iain and Mertens, Maria and Hevia, Eva (2017) Regioselective magnesiation of N-heterocyclic molecules: securing insecure cyclic anions by a β-diketiminate-magnesium clamp. Chemical Communications. ISSN 1359-7345 (https://doi.org/10.1039/C6CC09675A)

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Abstract

Using a specially designed magnesium metallating manifold, combining kinetically activated TMP amide base with a sterically amplified β-diketiminate ligand, this study has established a new regioselective strategy for magnesiation of challenging N-heterocyclic molecules. The broad scope of the approach is illustrated through reactions of pyrazine, triazoles and substituted pyridines through isolation and structural elucidation of their magnesiated intermediates.

ORCID iDs

Davin, Laia ORCID logoORCID: https://orcid.org/0000-0002-7927-4930, McLellan, Ross ORCID logoORCID: https://orcid.org/0000-0001-9700-0258, Hernán-Gómez, Alberto ORCID logoORCID: https://orcid.org/0000-0001-8150-7249, Clegg, Bill, Kennedy, A R ORCID logoORCID: https://orcid.org/0000-0003-3652-6015, Stepek, Iain, Mertens, Maria and Hevia, Eva ORCID logoORCID: https://orcid.org/0000-0002-3998-7506;
CORE (COnnecting REpositories)