Journal
PURE AND APPLIED CHEMISTRY
Volume 86, Issue 3, Pages 419-424Publisher
WALTER DE GRUYTER GMBH
DOI: 10.1515/pac-2014-5005
Keywords
alkylation; C-H functionalization; cobalt; imines
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A cobalt-N-heterocyclic carbene catalyst allows ortho-alkylation of aromatic imines with unactivated primary and secondary alkyl chlorides and bromides under room-temperature conditions. The scope of the reaction encompasses or complements that of cobalt-catalyzed ortho-alkylation reactions with olefins as alkylating agents that we developed previously. Stereochemical outcomes of secondary alkylation reactions suggest that the reaction involves single-electron transfer from a cobalt species to the alkyl halide to generate the corresponding alkyl radical. A cycloalkylated product obtained by this method can be transformed into unique spirocycles through manipulation of the directing group and the cycloalkyl groups.
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