Sustainable Synthesis of Quinolines and Pyrimidines Catalyzed by Manganese PNP Pincer Complexes

This study represents the first example an environmentally benign, sustainable, and practical synthesis of substituted quinolines and pyrimidines using combinations of 2-aminobenzyl alcohols and alcohols as well as benzamidine and two different alcohols, respectively. These reactions proceed with hi...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2016-12, Vol.138 (48), p.15543-15546
Main Authors: Mastalir, Matthias, Glatz, Mathias, Pittenauer, Ernst, Allmaier, Günter, Kirchner, Karl
Format: Article
Language:English
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Summary:This study represents the first example an environmentally benign, sustainable, and practical synthesis of substituted quinolines and pyrimidines using combinations of 2-aminobenzyl alcohols and alcohols as well as benzamidine and two different alcohols, respectively. These reactions proceed with high atom efficiency via a sequence of dehydrogenation and condensation steps that give rise to selective C–C and C–N bond formations, thereby releasing 2 equiv of hydrogen and water. A hydride Mn­(I) PNP pincer complex recently developed in our laboratory catalyzes this process in a very efficient way. A total of 15 different quinolines and 14 different pyrimidines were synthesized in isolated yields of up to 91 and 90%, respectively.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.6b10433