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Domino Oxidative [Pd]-Catalysis: One-Pot Synthesis of Fluorenones Starting from Simple Benzylamines and Iodo Arenes
D. Ravi Kumar,
Published in American Chemical Society
2015
Volume: 17
   
Issue: 23
Pages: 5894 - 5897
Abstract
A domino [Pd]-catalysis for the efficient synthesis of fluorenones is presented. The overall reaction proceeds through the formation of a five membered Pd(II)-cycle via a highly regioselective ortho C(sp2)-H activation(s) of simple benzylamine that combines with external iodo arenes to give ortho arylated products. Significantly, the reaction further activates the C(sp3)-H and C(sp2)-H (intramolecular oxidative Heck coupling) bonds to give tricyclic imine systems. Then the usual water workup affords the fused tricyclic ketones (fluorenones). Remarkably, this one-pot operation enabled the effective construction of two C-C to three C-C bonds © 2015 American Chemical Society.
About the journal
JournalData powered by TypesetOrganic Letters
PublisherData powered by TypesetAmerican Chemical Society
ISSN15237060