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Synfacts 2011(6): 0653-0653
DOI: 10.1055/s-0030-1260362
DOI: 10.1055/s-0030-1260362
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Ni-Catalyzed Alkyne Cycloaddition to Give Boronic Esters
Contributor(s):Paul Knochel, Andreas K. SteibA.-L. Auvinet, J. P. A. Harrity*
University of Sheffield, UK
A Nickel-Catalyzed Benzannulation Approach to Aromatic Boronic Esters
Angew. Chem. Int. Ed. 2011, 50: 2769-2772
University of Sheffield, UK
A Nickel-Catalyzed Benzannulation Approach to Aromatic Boronic Esters
Angew. Chem. Int. Ed. 2011, 50: 2769-2772
Further Information
Publication History
Publication Date:
19 May 2011 (online)
Key words
benzannulation - aromatic boronic esters - nickel
Significance
A new nickel-catalyzed benzannulation of cyclobutenones with alkynylboronates to yield aromatic boronic esters has been disclosed. Furthermore, a one-pot cycloaddition-coupling protocol has been developed, whereby the nickel catalyst performs firstly the benzannulation and afterwards the cross-coupling.
Comment
Alkynylboronates bearing sp³-based substituents show high selectivity for isomer A, whereas those bearing sp²-based substituents mainly favor isomer B.