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Synthesis 2009(21): 3533-3556  
DOI: 10.1055/s-0029-1218153
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Chroman-2-ones by Reduction of Coumarins

Volodymyr Semeniuchenko*a,b, Ulrich Grotha, Volodymyr Khilyab
a Fachbereich Chemie und Konstanz Research School Chemical Biology der Universität Konstanz, Fach M-720, Universitätsst. 10, 78457 Konstanz, Germany
Fax: +49(7531)884155; e-Mail: Ulrich.groth@uni-konstanz.de;
b Department of Chemistry, National Taras Shevchenko University, Volodymyrska str. 62, 01033 Kyiv-33, Ukraine
e-Mail: chem_vova@mail.univ.kiev.ua;
Further Information

Publication History

Received 26 May 2009
Publication Date:
07 October 2009 (online)

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Abstract

The scientific literature detailing the synthesis of chroman-2-ones by hydrogenation/reduction of the corresponding coumarins is reviewed. The following methods are described: hydrogenation on palladium, platinum, nickel, catalytic transfer hydrogenation, homogeneous hydrogenation, reduction by complex hydrides, reduction by metals, and electrochemical reduction. For each appropriate reaction, the yield, duration and some additional information is given (if available). Moreover, many exceptions and interesting transformations are described.

1 Introduction

2 Hydrogenation of Coumarins

3 Transfer Hydrogenation of Coumarins

4 Reduction of Coumarins with Metals

5 Reduction of Coumarins with Complex Hydrides

6 Homogeneous Hydrogenation of Coumarins

7 Electrochemical Reduction

8 Other Methods of Coumarin Reduction

9 Conclusion

Key words

heterocycles - reduction - heterogeneous catalysis - homogeneous catalysis - hydrogen transfer