Trimethyl borate (cas 121-43-7)-induced one-pot homologation reactions of isoquinoline with di-tert-butyl-TMP zincate

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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