54885-04-0Relevant articles and documents
Rhodium(III)-catalyzed C-C and C-O coupling of quinoline N-oxides with alkynes: Combination of C-H activation with o-atom transfer
Zhang, Xueyun,Qi, Zisong,Li, Xingwei
, p. 10794 - 10798 (2014)
[CpRhIII]-catalyzed C-H activation of arenes assisted by an oxidizing N-O or N-N directing group has allowed the construction of a number of hetercycles. In contrast, a polar N-O bond is well-known to undergo O-atom transfer (OAT) to alkynes. Despite the liability of N-O bonds in both C-H activation and OAT, these two important areas evolved separately. In this report, [CpRhIII] catalysts integrate both areas in an efficient redox-neutral coupling of quinoline N-oxides with alkynes to afford α-(8-quinolyl)acetophenones. In this process the N-O bond acts as both a directing group for C-H activation and as an O-atom donor. A chance meeting: A rhodium(III)-catalyzed redox-neutral coupling of quinoline N-oxides with alkynes has been realized, thus leading to the synthesis of α-substituted acetophenones. This system integrates C-H activation with O-atom transfer.
Cooperative catalysis by Ru and Pd for the direct coupling of a chelating aldehyde with iodoarenes or organostannanes
Ko, Sangwon,Kang, Byungman,Chang, Sukbok
, p. 455 - 457 (2005)
(Chemical Equation Presented) Two is better than one: The combination of two metallic catalyst systems effects transformations that are difficult to carry out with any single-catafyst systems. This is demonstrated by the coupling of 8-quinolinecarboxaldeh
Pd(II)-Catalyzed Arylation/Oxidation of Benzylic C-H of 8-Methylquinolines: Access to 8-Benzoylquinolines
Wang, Wenrong,Fu, Xiaoqing,Cai, Yuchen,Cheng, Li,Yao, Changsheng,Wang, Xiangshan,Li, Tuan-Jie
, p. 15423 - 15432 (2021/10/20)
An efficient access to 8-benzoylquinoline was developed by a sequential arylation/oxidation of 8-methylquinolines with aryl iodides in the presence of Pd(OAc)2. This transformation demonstrates good tolerance of a wide range of functional groups on aryl iodides, providing good to excellent yields of 8-benzoylquinolines.
Synthesis method of phenyl(quinolin-8-yl)-one derivative
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Paragraph 0009-0010; 0027-0028, (2021/08/07)
A synthesis method of a phenyl(quinolin-8-yl)-one derivative comprises the following steps: by taking 8-methylquinoline or substituted 8-methylquinoline and aryl iodide as raw materials, Ag2CO3 as an additive, KOAc as alkali and Pd(OAc)2 as a catalyst, reacting the raw materials in a solution formed by mixing hexafluoroisopropanol and glacial acetic acid according to a volume ratio of 3: 7, sealing a tube at 130 DEG C, and reacting for 24 hours to generate the target product. The synthesis process route is simple, and the highest yield reaches 87%.
Rhodium(III)-Catalyzed Direct Coupling of Quinoline-8-Carbaldehydes with (Het)Arylboronic Acids for the Synthesis of 8-Aryloylquinolines
Lyu, Xue-Li,Huang, Shi-Sheng,Huang, Yuan-Qiong,Li, Yong-Qiang,Song, Hong-Jian,Liu, Yu-Xiu,Wang, Qing-Min
, p. 10271 - 10282 (2020/09/03)
Herein, we describe a method for the synthesis of aryl-(het)aryl ketones by Rh(III)-catalyzed direct coupling between quinoline-8-carbaldehydes and (het)arylboronic acids. The method has a broad substrate scope, a high functional group tolerance, and uses
Oxidative coupling of Michael acceptors with aryl nucleophiles produced through rhodium-catalyzed C-C bond activation
Gregerson, Caroline E.,Trentadue, Kathryn N.,Phipps, Erik J. T.,Kirsch, Janelle K.,Reed, Katherine M.,Dyke, Gabriella D.,Jansen, Jacob H.,Otteman, Christian B.,Stachowski, Jessica L.,Johnson, Jeffrey B.
supporting information, p. 5944 - 5948 (2017/07/25)
Utilizing rhodium catalysis, aryl nucleophiles generated via carbon-carbon single bond activation successfully undergo oxidative coupling with Michael acceptors. The reaction scope encompasses a broad range of nucleophiles generated from quinolinyl ketones as well as a series of electron deficient terminal alkenes, illustrating the broad potential of intersecting carbon-carbon bond activation with synthetically useful coupling methodologies. The demonstrated oxidative coupling produces a range of cinnamyl derivatives, several of which are challenging to prepare via conventional routes.
Rhodium-Catalyzed Interconversion of Quinolinyl Ketones with Boronic Acids via C-C Bond Activation
Dennis, Joseph M.,Compagner, Chad T.,Dorn, Stanna K.,Johnson, Jeffrey B.
supporting information, p. 3334 - 3337 (2016/07/26)
A rhodium-catalyzed cross-coupling of aryl and aliphatic quinolinyl ketones with boronic acids has been developed. Proceeding via quinoline-directed carbon-carbon σ bond activation, the transformation demonstrates tolerance of a range of functional groups
Iridium- and rhodium-catalyzed C-H activation and formyl arylation of benzaldehydes under chelation-assistance
Yang, Xifa,Wang, He,Zhou, Xukai,Li, Xingwei
supporting information, p. 5233 - 5237 (2016/07/06)
Mild and efficient synthesis of benzophenones via Ir(iii)- and Rh(iii)-catalyzed, directing group-assisted formyl C-H arylation of benzaldehydes has been achieved using diaryliodonium salts, in which Rh(iii) and Ir(iii) catalysts exhibited a complementary
Catalytic formation of ketones from unactivated esters through rhodium chelation-assisted C-O bond activation
Wang, Jingjing,Zuo, Sujing,Chen, Weiqiang,Zhang, Xinrui,Tan, Kaixin,Tian, Yun,Wang, Jianhui
, p. 8217 - 8231 (2013/09/24)
A new method for building aryl aryl ketones containing heterocyclic rings through chelation-assisted C-O bond activation catalyzed by a rhodium complex has been developed. In this reaction, methyl quinoline-8-carboxylate, methyl quinoxaline-5-carboxylate, and their derivatives were reacted with an excess amount of a substituted phenyl boronic acid in the presence of a rhodium(I) complex to give substituted phenyl(quinolin-8-yl)methanone, phenylquinoxalin-5- ylmethanone, and their derivatives in medium to high yields. The current method offers a highly favorable synthetic pathway to efficiently build related drugs with an 8-benzoylquinoline core structure. This method may prove especially valuable for medicinal chemists for the late-stage introduction of versatile ketone moieties into complex scaffolds for diversity-oriented synthetic strategies.
Direct exchange of a ketone methyl or aryl group to another aryl group through ciC bond activation assisted by rhodium chelation
Wang, Jingjing,Chen, Weiqiang,Zuo, Sujing,Liu, Lu,Zhang, Xinrui,Wang, Jianhui
supporting information, p. 12334 - 12338 (2013/02/23)
Swapped: Commercially available quinolinone derivatives (1 or 2, see scheme) were reacted with arylboronic acids in the presence of a RhI complex to give aryl(quinolin-8-yl)methanone products 3 in medium to good yields. A mechanism that involves the in situ oxidation of RhI to RhIII by O2 in the presence of CuI was proposed. Copyright
