Synthesis of Phenanthridines via a Rhodium-Catalyzed C–C Bond Cleavage Reaction of Biphenylene with Nitriles

Aleš Korotvička; David Frejka; Zuzana Hampejsová; Ivana Císařová; Martin Kotora

doi:10.1055/s-0035-1561343

Synthesis, Table of Contents

Synthesis 2016; 48(07): 987-996
DOI: 10.1055/s-0035-1561343

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Synthesis of Phenanthridines via a Rhodium-Catalyzed C–C Bond Cleavage Reaction of Biphenylene with Nitriles

Aleš Korotvička

^aDepartment of Organic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 128 43 Praha 2, Czech Republic Email: kotora@natur.cuni.cz

,

David Frejka

^aDepartment of Organic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 128 43 Praha 2, Czech Republic Email: kotora@natur.cuni.cz

,

Zuzana Hampejsová

^aDepartment of Organic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 128 43 Praha 2, Czech Republic Email: kotora@natur.cuni.cz

,

Ivana Císařová

^bDepartment of Inorganic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 128 43 Praha 2, Czech Republic

,

Martin Kotora*

^aDepartment of Organic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 128 43 Praha 2, Czech Republic Email: kotora@natur.cuni.cz

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Abstract

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Abstract

The reaction of biphenylene with various nitriles in the presence of catalytic amount of [Rh(cod)₂BF₄]/dppe under microwave irradiation afforded 9-substituted phenanthridines. The reaction with alkyl and aromatic nitriles provided the corresponding 9-substituted phenanthridines in 26–79% isolated yields. The reaction was also carried out with cyanopyridines and it provided heterocyclic compounds with the bipyridine and terpyridine scaffold. The synthesized bipyridine and terpyridine were complexed with [Rh(cod)Cl]₂. The former provided a Rh(III) complex in which the cyclooctadiene moiety was oxidized to the tetrahydrofuran ring, whereas the latter gave a structurally fluxional complex (in solution) with only one pyridine ring coordinated to the rhodium atom.

Key words

C–C bond cleavage - rhodium - phenanthridine - catalysis - cycloaddition

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References

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