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Pd-catalyzed amination as an alternative to nucleophilic aromatic substitution for the synthesis of N-alkyltacrines and analogues.

ABSTRACT: A reliable Pd-catalyzed amination protocol is described for the synthesis of N-alkyltacrines and analogues. The Josiphos ligand CyPFtBu was found to provide optimum yields: 16 examples are given. Compared to the typical high-temperature nucleophilic aromatic substitution (NAS) routes, Pd-catalyzed aminations proceed at significantly lower reaction temperatures, and enable the synthesis of otherwise inaccessible products.

SUBMITTER: Ma M

PROVIDER: S-EPMC3030130 | biostudies-literature | 2011 Feb

REPOSITORIES: biostudies-literature

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Pd-catalyzed amination as an alternative to nucleophilic aromatic substitution for the synthesis of N-alkyltacrines and analogues.

Ma Ming M Mehta Jimit J Williams Larry D LD Carlier Paul R PR

Tetrahedron letters 20110201 8

A reliable Pd-catalyzed amination protocol is described for the synthesis of N-alkyltacrines and analogues. The Josiphos ligand CyPFtBu was found to provide optimum yields: 16 examples are given. Compared to the typical high-temperature nucleophilic aromatic substitution (NAS) routes, Pd-catalyzed aminations proceed at significantly lower reaction temperatures, and enable the synthesis of otherwise inaccessible products. ...[more]

PMID: 21286231

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