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Synthesis 2018; 50(07): 1555-1559
DOI: 10.1055/s-0036-1591881
paper
© Georg Thieme Verlag Stuttgart · New York

Direct and Stereoselective Iron-Catalyzed Amidation of Binor-S with Alkyl and Aryl Cyanides in Water

Ravil I. Khusnutdinov*
Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa, 450075, Russian Federation   Email: khusnutdinovri47@gmail.com
,
Tatyana M. Egorova
Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa, 450075, Russian Federation   Email: khusnutdinovri47@gmail.com
,
Leonard M. Khalilov
Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa, 450075, Russian Federation   Email: khusnutdinovri47@gmail.com
,
Ekaterina S. Meshcheriakova
Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa, 450075, Russian Federation   Email: khusnutdinovri47@gmail.com
,
Usein M. Dzhemilev
Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa, 450075, Russian Federation   Email: khusnutdinovri47@gmail.com
› Author AffiliationsThe work was financially supported by the Russian Foundation for Basic Research.
Further Information

Publication History

Received: 10 November 2017

Accepted after revision: 01 December 2017

Publication Date:
11 January 2018 (online)

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Abstract

The amidation of heptacyclo[8.4.0.02,12.03,8.04,6.05,9.011,13]tetra­decane (binor-S) with aceto-, propio-, valero-, and benzonitrile was performed in the presence of water and FeCl3·6H2O as catalyst to give the corresponding 10-exo-amidohexacyclo[9.2.1.02,7.03,5.04,8.09,13]tetradecanes. Hydrolysis of 10-exo-acetamidohexacyclo[9.2.1.02,7.03,5.04,8.09,13]tetra­decane with sodium hydroxide in n-butanol afforded 10-exo-aminohexacyclo[9.2.1.02,7.03,5.04,8.09,13]tetradecane in quantitative yield.

Key words

amidation - binor-S - organic nitriles - water - iron catalysts

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591881.
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