Chemoselective Copper-Catalyzed Ullmann-Type Coupling of Oxazolidinones with Bromoiodoarenes.

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Abstract

We describe the highly selective copper-catalyzed Ullmann-type coupling of bromoiodoarenes with oxazolidinones. 3,4,7,8-Tetramethyl-1,10-phenanthroline (Me4Phen) was identified as an optimal ligand promoting the desired C-N bond formation, while minimizing the competitive bromo-iodo exchange pathway that leads to formation of iodo-substituted and bis-coupled side products. The developed method is highly selective with a >98:2 ratio of the bromo- vs iodo-substituted compounds obtained in the isolated products.

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Journal

Journal ID (iso-abbrev): Org. Lett.

Title: Organic letters

Publisher: American Chemical Society (ACS)

ISSN (Electronic): 1523-7052

ISSN (Print): 1523-7052

Publication date (Electronic): May 22 2017

Affiliations

[1 ] Department of Small Molecule Process Chemistry, Genentech, Inc. , South San Francisco, California 94080, United States.

Article

DOI: 10.1021/acs.orglett.7b01304

PubMed ID: 28530104

SO-VID: a92c5e03-c3ed-4952-a12e-454303c829c7

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