Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
BCSJ Award Article
Scope and Limitations of Supramolecular Autoregulation
Abraham J. P. TeunissenRoy J. C. van der HaasJef A. J. M. VekemansAnja R. A. PalmansE. W. Meijer
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2016 Volume 89 Issue 3 Pages 308-314

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Abstract

Recently, our group has reported on the ureidopyrimidinone (UPy) induced buffering of 2,7-diamido-1,8-naphthyridine (NaPy) and used this phenomenon to regulate the catalysis of the Michael addition of 2,4-pentanedione to trans-β-nitrostyrene. We now show that the observed catalytic activity of NaPy is the result of a strong synergy between NaPy and trace amounts of K2CO3, resulting in a more than 100-fold increase in reaction rate compared to the two compounds separately. By keeping the concentration of K2CO3, as well as NaPy, constant, an improved regulation of the catalytic activity is achieved. We show that the catalytic activity can be precisely regulated in a noncovalent manner via the addition of the UPy motif. Finally, different salts and Michael substrates are screened to assess the selectivity of this catalytic couple and to provide a platform for future research in molecular buffering, regulation, and chemical networks.

We report on the use of 2,7-diamido-1,8-naphthyridine as phase-transfer catalyst for the Michael addition, whose activity can be regulated in a noncovalent manner via the complementary ureidopyrimidinone motif. The influence of this finding on previously reported results is discussed. Fullsize Image
 
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© 2016 The Chemical Society of Japan
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