Synthesis of N-perfluoroalkyl-3,4-disubstituted pyrroles by rhodium-catalyzed transannulation of N-fluoroalkyl-1,2,3-triazoles with terminal alkynes

Synthesis of N-perfluoroalkyl-3,4-disubstituted pyrroles by rhodium-catalyzed transannulation of N-fluoroalkyl-1,2,3-triazoles with terminal alkynes

The rhodium-catalyzed transannulation of N-perfluoroalkyl-1,2,3-triazoles with aromatic and aliphatic terminal alkynes under microwave heating conditions afforded N-perfluoroalkyl-3,4-disubstituted pyrroles (major products) and N-fluoroalkyl-2,4-disubstituted pyrroles (minor products). The observed...

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Main Authors: Olga Bakhanovich, Viktor Khutorianskyi, Vladimir Motornov, Petr Beier
Format: Article
Language:English
Published: Beilstein-Institut 2021-02-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
pyrrole
transannulation
rhodium carbene
triazole
Online Access:https://doi.org/10.3762/bjoc.17.44
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spelling doaj-aea90d4515764276915fae78a1565c352021-03-09T13:46:07ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972021-02-0117150451010.3762/bjoc.17.441860-5397-17-44Synthesis of N-perfluoroalkyl-3,4-disubstituted pyrroles by rhodium-catalyzed transannulation of N-fluoroalkyl-1,2,3-triazoles with terminal alkynesOlga Bakhanovich0Viktor Khutorianskyi1Vladimir Motornov2Petr Beier3Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo náměstí 2, 166 10 Prague 6, Czech RepublicInstitute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo náměstí 2, 166 10 Prague 6, Czech RepublicInstitute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo náměstí 2, 166 10 Prague 6, Czech RepublicInstitute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo náměstí 2, 166 10 Prague 6, Czech RepublicThe rhodium-catalyzed transannulation of N-perfluoroalkyl-1,2,3-triazoles with aromatic and aliphatic terminal alkynes under microwave heating conditions afforded N-perfluoroalkyl-3,4-disubstituted pyrroles (major products) and N-fluoroalkyl-2,4-disubstituted pyrroles (minor products). The observed selectivities in the case of the reactions with aliphatic alkynes were high.https://doi.org/10.3762/bjoc.17.44pyrroletransannulationrhodium carbenetriazole
collection DOAJ
language English
format Article
sources DOAJ
author Olga Bakhanovich
Viktor Khutorianskyi
Vladimir Motornov
Petr Beier
spellingShingle Olga Bakhanovich
Viktor Khutorianskyi
Vladimir Motornov
Petr Beier
Synthesis of N-perfluoroalkyl-3,4-disubstituted pyrroles by rhodium-catalyzed transannulation of N-fluoroalkyl-1,2,3-triazoles with terminal alkynes
Beilstein Journal of Organic Chemistry
pyrrole
transannulation
rhodium carbene
triazole
author_facet Olga Bakhanovich
Viktor Khutorianskyi
Vladimir Motornov
Petr Beier
author_sort Olga Bakhanovich
title Synthesis of N-perfluoroalkyl-3,4-disubstituted pyrroles by rhodium-catalyzed transannulation of N-fluoroalkyl-1,2,3-triazoles with terminal alkynes
title_short Synthesis of N-perfluoroalkyl-3,4-disubstituted pyrroles by rhodium-catalyzed transannulation of N-fluoroalkyl-1,2,3-triazoles with terminal alkynes
title_full Synthesis of N-perfluoroalkyl-3,4-disubstituted pyrroles by rhodium-catalyzed transannulation of N-fluoroalkyl-1,2,3-triazoles with terminal alkynes
title_fullStr Synthesis of N-perfluoroalkyl-3,4-disubstituted pyrroles by rhodium-catalyzed transannulation of N-fluoroalkyl-1,2,3-triazoles with terminal alkynes
title_full_unstemmed Synthesis of N-perfluoroalkyl-3,4-disubstituted pyrroles by rhodium-catalyzed transannulation of N-fluoroalkyl-1,2,3-triazoles with terminal alkynes
title_sort synthesis of n-perfluoroalkyl-3,4-disubstituted pyrroles by rhodium-catalyzed transannulation of n-fluoroalkyl-1,2,3-triazoles with terminal alkynes
publisher Beilstein-Institut
series Beilstein Journal of Organic Chemistry
issn 1860-5397
publishDate 2021-02-01
description The rhodium-catalyzed transannulation of N-perfluoroalkyl-1,2,3-triazoles with aromatic and aliphatic terminal alkynes under microwave heating conditions afforded N-perfluoroalkyl-3,4-disubstituted pyrroles (major products) and N-fluoroalkyl-2,4-disubstituted pyrroles (minor products). The observed selectivities in the case of the reactions with aliphatic alkynes were high.
topic pyrrole
transannulation
rhodium carbene
triazole
url https://doi.org/10.3762/bjoc.17.44
work_keys_str_mv AT olgabakhanovich synthesisofnperfluoroalkyl34disubstitutedpyrrolesbyrhodiumcatalyzedtransannulationofnfluoroalkyl123triazoleswithterminalalkynes
AT viktorkhutorianskyi synthesisofnperfluoroalkyl34disubstitutedpyrrolesbyrhodiumcatalyzedtransannulationofnfluoroalkyl123triazoleswithterminalalkynes
AT vladimirmotornov synthesisofnperfluoroalkyl34disubstitutedpyrrolesbyrhodiumcatalyzedtransannulationofnfluoroalkyl123triazoleswithterminalalkynes
AT petrbeier synthesisofnperfluoroalkyl34disubstitutedpyrrolesbyrhodiumcatalyzedtransannulationofnfluoroalkyl123triazoleswithterminalalkynes
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