Synthesis of Pyridobenzazepines Using a One-Pot Rh/Pd-Catalyzed Process

In recent years, our group has been developing multicatalytic reactions for the synthesis of biologically relevant heterocyclic compounds. An efficient dual-metal catalyzed reaction of electron-deficient o-chlorovinylpyridines with o-aminophenylboronic esters to access pyridobenzazepines is describe...

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Bibliographic Details
Published in:Journal of organic chemistry 2017-06, Vol.82 (12), p.6089-6099
Main Authors: Lam, Heather, Tsoung, Jennifer, Lautens, Mark
Format: Article
Language:English
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Summary:In recent years, our group has been developing multicatalytic reactions for the synthesis of biologically relevant heterocyclic compounds. An efficient dual-metal catalyzed reaction of electron-deficient o-chlorovinylpyridines with o-aminophenylboronic esters to access pyridobenzazepines is described. Combining a RhI-catalyzed arylation followed by a Pd0-catalyzed C–N coupling, in a one-pot procedure, provides a simplified method to access heterocycles without workup and purification after each step. The substrate scope encompasses a variety of N-H and N-alkylated pyridobenzazepine variants with yields up to 93%.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b00568