Modular o-Quinone Catalyst System for Dehydrogenation of Tetrahydroquinolines under Ambient Conditions
Author(s) -
Alison E. Wendlandt,
Shan S. Stahl
Publication year - 2014
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/ja506546w
Subject(s) - dehydrogenation , chemistry , catalysis , quinone , combinatorial chemistry , pharmacophore , organic chemistry , stereochemistry
Quinolines are common pharmacophores present in numerous FDA-approved pharmaceuticals and other bioactive compounds. Here, we report the design and development of new o-quinone-based catalysts for the oxidative dehydrogenation of tetrahydroquinolines to afford quinolines. Use of a Co(salophen) cocatalyst allows the reaction to proceed efficiently with ambient air at room temperature. The utility of the catalytic method is demonstrated in the preparation of a number of medicinally relevant quinolines.
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