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Synfacts 2017; 13(12): 1265
DOI: 10.1055/s-0036-1591701
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed cis-Selective Hydrogenation of Fluoroarenes

Contributor(s):
Hisashi Yamamoto
,
Takahiro Sawano
Wiesenfeldt MP. Nairoukh Z. Li W. Glorius F. * Westfälische Wilhelms-Universität Münster, Germany
Hydrogenation of Fluoroarenes: Direct Access to All-cis-(Multi)fluorinated Cycloalkanes.

Science 2017;
357: 908-912
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Further Information

Publication History

Publication Date:
17 November 2017 (online)

 
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Key words

rhodium catalysis - hydrogenation - stereoselectivity - fluoroarenes - fluorocycloalkanes

Significance

All-cis-polyfluorinated cycloalkanes exhibit attractive electronic properties due to their high dipole moments. However, multistep syntheses from diastereoselectively fluorinated precursors are generally required. The authors report a rhodium/cyclic (alkyl)(amino)(carbene) complex catalyzed cis-selective hydrogenation of fluorinated arenes to provide a variety of highly diastereoselectively fluorinated cycloalkanes.


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Comment

To suppress the formation of hydrodefluorinated byproducts, the choice of a less-polar solvent such as hexane is important.


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