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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Copper-Catalyzed ortho-Functionalization of Quinoline N-Oxides with Vinyl Arenes
Hu, Hui,Hu, Xiaoping,Liu, Yuanhong
supporting information, p. 18975 - 18979 (2020/08/25)
An efficient copper-catalyzed regioselective C?H alkenylation and borylative alkylation of quinoline N-oxides with vinyl arenes in the presence of pinacol diborane has been developed. The reaction proceeds through the borylcupration of the vinyl arenes followed by nucleophilic attack of the resulting alkyl copper species to the quinoline N-oxides. Benzoquinone and KOtBu were identified as the necessary additives at the second step of the reaction that are crucial for the success of the reaction. A wide range of C2-functionalizaed quinolines were obtained with good functional group tolerance, which may find utilities in pharmaceuticals and synthetic chemistry.
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.