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

被引：10

作者：

Korotvicka, Ales ^{[1
]}

Frejka, David ^{[1
]}

Hampejsova, Zuzana ^{[1
]}

Cisarova, Ivana ^{[2
]}

Kotora, Martin ^{[1
]}

机构：

[1] Charles Univ Prague, Dept Organ Chem, Fac Sci, Hlavova 8, Prague 12843 2, Czech Republic

[2] Charles Univ Prague, Dept Inorgan Chem, Fac Sci, Hlavova 8, Prague 12843 2, Czech Republic

来源：

SYNTHESIS-STUTTGART | 2016年 / 48卷 / 07期

关键词：

C-C bond cleavage; rhodium; phenanthridine; catalysis; cycloaddition; CARBON-CARBON BOND; ATROPOISOMERIC BIPYRIDINE N; N'-DIOXIDES; PYRIDINE N-OXIDES; ENANTIOSELECTIVE ALLYLATION; ASYMMETRIC ALLYLATION; AROMATIC-ALDEHYDES; PALLADIUM CATALYSIS; NICKEL(0) COMPLEXES; OLEFIN-OXYGENATION; OXIDATIVE ADDITION;

D O I：

10.1055/s-0035-1561343

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of biphenylene with various nitriles in the presence of catalytic amount of [Rh(cod)(2)BF4]/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.

引用

页码：987 / 996

页数：10

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