1. Hydroarylation of Alkynes with Phenols in the Presence of Gallium Complexes of a Labile N-Ligand: Synthesis of Chromenes.
- Author
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Moskalev, Mikhail V., Yakub, Arkadiy M., Morozov, Alexander G., Baranov, Evgenii V., Kazarina, Olga V., and Fedushkin, Igor L.
- Subjects
ALKYNES ,LIGANDS (Chemistry) ,GALLIUM ,OXYGEN ,HETEROCYCLIC compounds - Abstract
In the presence of (dpp-bian)Ga-Ga(dpp-bian) ( 1) and [dpp-bian(Ph)C=C(H)]Ga-Ga[(H)C=C(Ph)dpp-bian] ( 2) {dpp-bian = 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene}, phenylacetylene reacts with 1-naphthol to give 2-(1-phenylvinyl)naphthalen-1-ol ( 3). In solution in the presence of complexes 1 or 2, compound 3 undergoes further dimerization to give 2-[4-methyl-2,4-diphenyl-3,4-dihydro-2 H-benzo[ h]chromen-2-yl]naphthalen-1-ol (C
36 H28 O2 ), whose diastereomers 4 and 5 were isolated in crystalline form. Diastereomer 4 is the kinetically favored product, which, however, undergoes conversion into diastereomer 5 in solution at elevated temperature. The structures of 4 and 5 were determined by single-crystal X-ray analysis. The catalytic activity of complexes 1 and 2 in the hydroarylation reactions of phenylacetylene and some other alkynes with different arenes has been investigated. By the reaction of phenylacetylene with 3,5-di- tert-butylphenol, 5,7-di- tert-butyl-4-methyl-2,4-diphenyl-4 H-chromene ( 7) has been prepared for the first time. [ABSTRACT FROM AUTHOR]- Published
- 2015
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