863487-46-1Relevant articles and documents
Convenient synthesis of quinolines from α-2-nitroaryl alcohols and alcohols via a ruthenium-catalyzed hydrogen transfer strategy
Xie, Feng,Zhang, Min,Chen, Mengmeng,Lv, Wan,Jiang, Huanfeng
, p. 349 - 353 (2015)
A new and straightforward method for convenient synthesis of quinolines via a ruthenium-catalyzed hydrogen-transfer strategy has been demonstrated. By employing a commercially available ruthenium catalyst system, different α-2-nitroaryl alcohols were efficiently converted in combination with a variety of alcohols into various substituted products in reasonable to good yields upon isolation. The synthetic protocol is operationally simple with a broad substrate scope, and there is no need for the use of specialized reducing agents, making it a practical approach for versatile preparation of various quinoline derivatives.
Practical Ni-Catalyzed Cross-Coupling of Unsaturated Zinc Pivalates with Unsaturated Nonaflates and Triflates
Hofmayer, Maximilian S.,Lutter, Ferdinand H.,Grokenberger, Lucie,Hammann, Jeffrey M.,Knochel, Paul
supporting information, p. 36 - 39 (2019/01/04)
A practical nickel-catalyzed cross-coupling of (hetero)aryl or alkynylzinc pivalates with various unsaturated nonaflates or triflates is described. Organozinc pivalates allow these cross-couplings to take place with high yields and a low catalyst loading (0.5 mol %). Couplings with (E)- and (Z)-alkenyl triflates proceed with retention of configuration.
Nickel complexes supported by quinoline-based ligands: Synthesis, characterization and catalysis in the cross-coupling of arylzinc reagents and aryl chlorides or aryltrimethylammonium salts
Zhang, Qiang,Zhang, Xue-Qi,Wang, Zhong-Xia
, p. 10453 - 10464,12 (2020/08/31)
Lithium and nickel complexes bearing quinoline-based ligands have been synthesized and characterized. Reaction of 8-azidoquinoline with Ph 2PNHR (R = p-MeC6H4, But) affords N-(8-quinolyl)iminophosphoranes RNHP(Ph2)N(8-C9H 6N) (1a, R = p-MeC6H4; 1b, R = But. C9H6N = quinolyl)). Reaction of 1a with (DME)NiCl 2 generates a nickel complex [NiCl2{N(8-C 9H6N)P(Ph2)NH(p-MeC6H4)}] (2a). Treatment of 1b with (DME)NiCl2 and following with NaH produces [NiCl{(1,2-C6H4)P(Ph)(NHBut)N(8-C 9H6N)}] (4). Complex 4 was also obtained by reaction of (DME)NiCl2 with [Li{(1,2-C6H4)P(Ph)(NHBu t)N(8-C9H6N)}] (5) prepared through lithiation of 1b. Reaction of 2-PyCH2P(Ph2)N(8-C9H 6N) (6, Py = pyridyl) and PhNC(Ph)CH2P(Ph 2)N(8-C9H6N) (8), respectively, with (DME)NiCl2 yields two five-coordinate N,N,N-chelate nickel complexes, [NiCl2{2-PyCH2P(Ph2)N(8-C9H 6N)}] (7) and [NiCl2{PhNC(Ph)CH2P(Ph 2)N(8-C9H6N)}] (9). Similar reaction between Ph2PCH2P(Ph2)N(8-C9H6N) (10) and (DME)NiCl2 results in five-coordinate N,N,P-chelate nickel complex [NiCl2{Ph2PCH2P(Ph2)N(8- C9H6N)}] (11). Treatment of [(8-C9H 6N)NP(Ph2)]2CH2 (12) [prepared from (Ph2P)2CH2 and 2 equiv. of 8-azidoquinoline] with LiBun and (DME)NiCl2 successively affords [NiCl{(8-C9H6N)NP(Ph2)}2CH] (13). The new compounds were characterized by 1H, 13C and 31P NMR spectroscopy (for the diamagnetic compounds), IR spectroscopy (for the nickel complexes) and elemental analysis. Complexes 2a, 4, 7, 9, 11 and 13 were also characterized by single-crystal X-ray diffraction techniques. The nickel complexes were evaluated for the catalysis in the cross-coupling reactions of arylzinc reagents with aryl chlorides and aryltrimethylammonium salts. Complex 7 exhibits the highest activity among the complexes in catalyzing the reactions of arylzinc reagents with either aryl chlorides or aryltrimethylammonium bromides.
