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.
Heterogenous catalytic method for the synthesis of biquinolines and bipyridines
Aksenov,Goncharov
, p. 1491 - 1492 (2008)
A method has been developed for the synthesis of 2,2′- and 3,3′-biquinolines and of 4,4′-bipyridine based on the coupling of 2- and 3-bromoquinoline or 4-bromopyridine using a Pd/C-hydrazine-KOH catalytic system.
Synthesis and Reaction of 2,2'-Biquinolyl
Wakabayashi, Shoji,Kubo, Yukihiro,Takeda, Takashi,Uenishi, Jun-ichi,Oae, Shigeru
, p. 2338 - 2341 (1989)
A title compound is readily prepared from methyl 2-quinolyl sulfoxide (3) with methylmagnesium bromide in excellent yield and an ipso addition of alkylmagnesium halides to 2,2'-biquinolyl (4) is also described.
First cross-coupling reactions of arylmagnesates: A convenient access to heteroarylquinolines
Dumouchel, Sylvain,Mongin, Florence,Trécourt, Fran?ois,Quéguiner, Guy
, p. 3877 - 3880 (2003)
2-, 3- and 4-Bromoquinolines were converted to the corresponding lithium tri(quinolyl)magnesates at -10°C on treatment with Bu3MgLi in THF. The resulting organomagnesium derivatives were involved in catalyzed cross-coupling reactions with heteroaryl bromides and chlorides to afford functionalized quinolines.
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.
Homocoupling of aryl halides using Nickel(II) complex and zinc in the presence of Et4NI. An efficient method for the synthesis of biaryls and bipyridines
Iyoda,Otsuka,Sato,Nisato,Oda
, p. 80 - 87 (1990)
Reduction of NiX2(PPh3)2 with zinc in the presence of Et4NI gives a nickel catalyst which has been proven to be useful for the coupling of aryl halides. This nickel catalyst can be prepared in THF without an additional triphenylphosphine and is effective for the homocoupling of aryl chlorides, bromides, and iodides to produce biaryls and bipyridines in good yields. The reported new approach provides a simple access to novel derivatives of biaryls and bipyridines.
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
Ruthenium(II) Complexes with Three Different Diimine Ligands
Zelewsky, Alex,Gremaud, Gabriel
, p. 1108 - 1115 (1988)
The synthesis of tris-heteroleptic complexes of Ru(II) with diimine ligands is descriebed.Ten compounds 2 (R=H, CH3; L=2,2'-bipyridine (bpy), 4,4'-dimethyl-2,2'-bipyridine (Me2bpy), 2,2'-bipyrimidine (bpm), 2,2'-biisoquinoline (bii
Highly Ordered Mesoporous Cobalt Oxide as Heterogeneous Catalyst for Aerobic Oxidative Aromatization of N-Heterocycles
Cao, Yue,Wu, Yong,Zhang, Yuanteng,Zhou, Jing,Xiao, Wei,Gu, Dong
, p. 3679 - 3686 (2021/06/18)
N-heterocycles are key structures for many pharmaceutical intermediates. The synthesis of such units normally is conducted under homogeneous catalytic conditions. Among all methods, aerobic oxidative aromatization is one of the most effective. However, in homogeneous conditions, catalysts are difficult to be recycled. Herein, we report a heterogeneous catalytic strategy with a mesoporous cobalt oxide as catalyst. The developed protocol shows a broad applicability for the synthesis of N-heterocycles (32 examples, up to 99 % yield), and the catalyst presents high turnover numbers (7.41) in the absence of any additives. Such a heterogenous approach can be easily scaled up. Furthermore, the catalyst can be recycled by simply filtration and be reused for at least six times without obvious deactivation. Comparative studies reveal that the high surface area of mesoporous cobalt oxide plays an important role on the catalytic reactivity. The outstanding recycling capacity makes the catalyst industrially practical and sustainable for the synthesis of diverse N-heterocycles.
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.
