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

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