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Access to 2-(Het)aryl and 2-Styryl Benzoxazoles via Palladium-Catalyzed Aminocarbonylation of Aryl and Vinyl Bromides

Karoline T. Neumann, Anders T. Lindhardt*, Benny Bang-Andersen and Troels Skrydstrup*

*Interdisciplinary Nanoscience Center (iNANO), Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus C, Denmark, Email: tschem.au.dk, lindhardteng.au.dk

K. T. Neumann, A. T. Lindhardt, B. Bang-Andersen, T. Skrydstrup, Org. Lett., 2015, 17, 2094-2097.

DOI: 10.1021/acs.orglett.5b00642 (free Supporting Information)


Abstract

A sequential one-pot procedure for the synthesis of either 2-(hetero)aryl or 2-styryl benzoxazoles from aryl and vinyl bromides involves an initial aminocarbonylation with 2-aminophenols as nucleophiles followed by an acid mediated ring closure to generate the heterocycle. The methodology displays a broad substrate scope in good yields.

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Key Words

benzoxazoles


ID: J54-Y2015