119-91-5Relevant articles and documents
Nickel-Catalyzed Electrochemical Reductive Homocouplings of Aryl and Heteroaryl Halides: A Useful Route to Symmetrical Biaryls
Rahil, Rima,Sengmany, Stéphane,Le Gall, Erwan,Léonel, Eric
, p. 146 - 154 (2018)
Due to their widespread presence in functional materials and pharmaceuticals, biaryls are of fundamental importance in organic chemistry. Methods for the synthesis of symmetrical biaryls generally involve both metallic reduction and transition-metal catalysis. In this work, we show that electroreduction can also constitute a very relevant way to achieve the nickel-catalyzed reductive synthesis of symmetrical biaryl compounds. Therefore, it is demonstrated that both aryl and heteroaryl halides undergo reductive coupling to furnish the corresponding symmetrical biaryls in fair to excellent yields. Reactions are performed under very mild conditions thus ensuring important functional group tolerance.
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Gershuns,Pustovar
, (1971)
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Jackson et al.
, p. 1126,1127, 1130, 1131 (1963)
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A [2 + 3] Reductive Cyclodimerization of Quinoline by SmI2
Yella, Ramesh,Gottlieb, Hugo E.,Hoz, Shmaryahu
, p. 8929 - 8932 (2015)
Pyridine and its derivatives are rather difficult to reduce, and the products often undergo a very fast reoxidation to regain aromaticity. The reduction of quinoline by SmI2 results in an instantaneous [2 + 3] cyclization reaction, forming a bridged seven-membered ring within a polycyclic system.
Synthesis and coordination behaviour of aluminate-based quinolyl ligands
Bond, Andrew D.,Colebatch, Annie L.,García-Rodríguez, Raul,Hanf, Schirin,Rincón-Nocito, Marina,Waters, Jessica E.,Wright, Dominic S.
, p. 14551 - 14559 (2021)
The effects of moving the donor N-atom from the 2-position in lithium (2-pyridyl)- and (2-quinolyl)aluminates to the more remote position in (8-quinolyl)aluminates have been investigated by solid-state structural and DFT computational studies of the new c
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Badr,Aly
, p. 3401,3405 (1972)
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Sheinkman et al.
, (1977)
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A Mild Method for Electrochemical Reduction of Heterocyclic N-Oxides
Fukazawa, Yasuaki,Rubtsov, Aleksandr E.,Malkov, Andrei V.
supporting information, p. 3317 - 3319 (2020/05/25)
Deoxygenation of heteroaromatic N-oxides is commonly accomplished using chemical or enzymatic methods. In this work, we report on an expedient protocol for electrochemical reduction of pyridine N-oxide derivatives under mild conditions. A diverse range of mono- and bis N-oxides were converted into the corresponding nitrogen bases in good yields. Importantly, the method is highly selective towards N-oxides and tolerates challenging halo and nitro substituents in the heteroaromatic ring.
Dehydrogenative Synthesis of 2,2′-Bipyridyls through Regioselective Pyridine Dimerization
Yamada, Shuya,Kaneda, Takeshi,Steib, Philip,Murakami, Kei,Itami, Kenichiro
supporting information, p. 8341 - 8345 (2019/04/30)
2,2′-Bipyridyls have been utilized as indispensable ligands in metal-catalyzed reactions. The most streamlined approach for the synthesis of 2,2′-bipyridyls is the dehydrogenative dimerization of unfunctionalized pyridine. Herein, we report on the palladium-catalyzed dehydrogenative synthesis of 2,2′-bipyridyl derivatives. The Pd catalysis effectively works with an AgI salt as the oxidant in the presence of pivalic acid. A variety of pyridines regioselectively react at the C2-positions. This dimerization method is applicable for challenging substrates such as sterically hindered 3-substituted pyridines, where the pyridines regioselectively react at the C2-position. This reaction enables the concise synthesis of twisted 3,3′-disubstituted-2,2′-bipyridyls as an underdeveloped class of ligands.
