Benign synthesis of indoles from anilines and epoxides: new application for ruthenium pincer catalysts

For the first time, ruthenium pincer complexes such as Ru-MACHO-BH were successfully used as catalysts in the domino-synthesis of indoles from anilines and epoxides. Following previously optimised procedures, a variety of indoles were produced in an atom-efficient manner with water and hydrogen as t...

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Published inChimia Vol. 68; no. 4; p. 231
Main Authors Monney, Angèle, Peña-López, Miguel, Beller, Matthias
Format Journal Article
LanguageEnglish
Published Switzerland Swiss Chemical Society 01.01.2014
Subjects
Alcohol dehydrogenative activation
Anilines and epoxides
Indole synthesis
Ru-macho-bh
Ruthenium pincer catalyst
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Abstract For the first time, ruthenium pincer complexes such as Ru-MACHO-BH were successfully used as catalysts in the domino-synthesis of indoles from anilines and epoxides. Following previously optimised procedures, a variety of indoles were produced in an atom-efficient manner with water and hydrogen as the only stoichiometric side-products. The β-amino alcohol, resulting from the ring-opening of the epoxide with the aniline derivative, undergoes dehydrogenation, followed by condensation with excess aniline and the final intramolecular cyclisation affords the desired indole. Ru-MACHO-BH showed similar catalytic activity than our previously reported in situ prepared catalyst (Ru3(CO)12/dppf) without further optimisation of the reaction conditions.
AbstractList For the first time, ruthenium pincer complexes such as Ru-MACHO-BH were successfully used as catalysts in the domino-synthesis of indoles from anilines and epoxides. Following previously optimised procedures, a variety of indoles were produced in an atom-efficient manner with water and hydrogen as the only stoichiometric side-products. The ?-amino alcohol, resulting from the ring-opening of the epoxide with the aniline derivative, undergoes dehydrogenation, followed by condensation with excess aniline and the final intramolecular cyclisation affords the desired indole. Ru-MACHO-BH showed similar catalytic activity than our previously reported in situ prepared catalyst (Ru3(CO)12/dppf) without further optimisation of the reaction conditions.
For the first time, ruthenium pincer complexes such as Ru-MACHO-BH were successfully used as catalysts in the domino-synthesis of indoles from anilines and epoxides. Following previously optimised procedures, a variety of indoles were produced in an atom-efficient manner with water and hydrogen as the only stoichiometric side-products. The β-amino alcohol, resulting from the ring-opening of the epoxide with the aniline derivative, undergoes dehydrogenation, followed by condensation with excess aniline and the final intramolecular cyclisation affords the desired indole. Ru-MACHO-BH showed similar catalytic activity than our previously reported in situ prepared catalyst (Ru3(CO)12/dppf) without further optimisation of the reaction conditions.
Author Beller, Matthias
Peña-López, Miguel
Monney, Angèle
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  organization: Leibniz-Institut für Katalyse e.V. an der Universität, Rostock, Albert-Einstein-Strasse 29a, D-18059 Rostock, Germany. matthias.beller@catalysis.de
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SubjectTerms Alcohol dehydrogenative activation
Anilines and epoxides
Indole synthesis
Ru-macho-bh
Ruthenium pincer catalyst
Title Benign synthesis of indoles from anilines and epoxides: new application for ruthenium pincer catalysts
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