☆ 4.7 Article

Sulfoximine-Assisted One-Pot Unsymmetrical Multiple Annulation of Arenes: A Combined Experimental and Computational Study

JOURNAL OF ORGANIC CHEMISTRY (2018)

Journal

JOURNAL OF ORGANIC CHEMISTRY

Volume 83, Issue 17, Pages 9667-9681

Publisher

AMER CHEMICAL SOC

DOI: 10.1021/acs.joc.8b01077

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Categories

Chemistry, Organic

Funding

SERB [EMR/2014/385]
CSIR, India

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Abstract

Discussed herein is an unprecedented Ru-catalyzed one-pot unsymmetrical C-H difunctionalization of arenes comprising intramolecular hydroarylation of olefins and intermolecular annulation of alkynes. This unprecedented 2-fold C-H functionalization is validated on the basis of experimental and density functional theory (DFT) study. The transformation readily occurs with the assistance of methyl-phenyl sulfoximine (MPS) directing group in the presence of Ru catalyst forming two C-C and one C-N bonds in a single operation. The overall process is atom economical and step-efficient and provides unusual dihydrofuran-fused isoquinolone heterocycles. Further annulation of NH and the proximal o-C- H-arene of isoquinolone with alkynes build highly conjugated novel polycyclic compounds. Overall, three independent annulations in arene motifs are visualized and thoughtfully executed; finally, S ring-fused structural entities are constructed forming three C-C and two C-N bonds.

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