Add time:09/06/2019 Source:sciencedirect.com
Novel one-pot homologation reactions of isoquinoline and quinoline with di-tert-butyl-TMP zincate/trimethyl borate are described. 1-tert-Butyl-3,4-dihydroisoquinoline 1 and 1-tert-butylisoquinoline 2 are formed unexpectedly under the presented reaction conditions with relative ease. A reaction mechanism, including 1,2-migration of the tert-butyl group from 1-isoquinolylzincate, is proposed in detail. Migratory aptitudes of other ligands of isoquinolyl zincates are also discussed.
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