Alkynylboronic Esters as Efficient Dienophiles in Cobalt-Catalyzed Diels-Alder Reactions

Gerhard Hilt*, Konstantin I. Smolko

*Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße, 35043 Marburg, Deutschland, Email: hiltchemie.uni-marburg.de

G. Hilt, K. I. Smolko, Angew. Chem. Int. Ed., 2003, 42, 2795-2797.

DOI: 10.1002/anie.200351404

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Abstract

The cobalt-catalyzed Diels-Alder reaction of alkynyl pinacol boronic esters with various dienes generates cycloadducts in very good regioselectivity. A reaction sequence (Diels-Alder reaction, Suzuki coupling, DDQ oxidation) was successfully performed as a one pot operation without isolation of the intermediates.

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Regioselective Cobalt-Catalyzed Diels-Alder Reaction towards 1,3-Disubstituted and 1,2,3-Trisubstituted Benzene Derivatives

G. Hilt, M. Danz, Synthesis, 2008, 2257-2263.

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Key Words

alkynes, boron compounds, Diels-Alder Reaction, dihydroaromatic compounds, arenes, Suzuki reaction, vinylboronates, DDQ

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ID: J06-Y2003-110