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Rhodium(III)-Catalyzed Direct Coupling of Quinoline-8-Carbaldehydes with (Het)Arylboronic Acids for the Synthesis of 8-Aryloylquinolines.
J Org Chem. 2020 08 07; 85(15):10271-10282.JO

Abstract

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 commercially available starting materials. Scale-up of the reaction and subsequent synthesis of tubulin polymerization inhibitor demonstrated its utilities. A plausible mechanism was proposed on the basis of the fact that a stable cycloacylrhodium intermediate complex could be used as catalyst, and the complex reacted stoichiometrically with (het)arylboronic acids.

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Authors+Show Affiliations

State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, People's Republic of China.

State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, People's Republic of China.

State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, People's Republic of China.

State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, People's Republic of China.

State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, People's Republic of China.

State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, People's Republic of China.

State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, People's Republic of China. Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, People's Republic of China.

MeSH

Boronic AcidsCatalysisKetonesQuinolinesRhodium

Pub Type(s)

Journal Article

Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

32664730

Citation

Lyu, Xue-Li, et al. "Rhodium(III)-Catalyzed Direct Coupling of Quinoline-8-Carbaldehydes With (Het)Arylboronic Acids for the Synthesis of 8-Aryloylquinolines." The Journal of Organic Chemistry, vol. 85, no. 15, 2020, pp. 10271-10282.

Lyu XL, Huang SS, Huang YQ, et al. Rhodium(III)-Catalyzed Direct Coupling of Quinoline-8-Carbaldehydes with (Het)Arylboronic Acids for the Synthesis of 8-Aryloylquinolines. J Org Chem. 2020;85(15):10271-10282.

Lyu, X. L., Huang, S. S., Huang, Y. Q., Li, Y. Q., Song, H. J., Liu, Y. X., & Wang, Q. M. (2020). Rhodium(III)-Catalyzed Direct Coupling of Quinoline-8-Carbaldehydes with (Het)Arylboronic Acids for the Synthesis of 8-Aryloylquinolines. The Journal of Organic Chemistry, 85(15), 10271-10282. https://doi.org/10.1021/acs.joc.0c01490

Lyu XL, et al. Rhodium(III)-Catalyzed Direct Coupling of Quinoline-8-Carbaldehydes With (Het)Arylboronic Acids for the Synthesis of 8-Aryloylquinolines. J Org Chem. 2020 08 7;85(15):10271-10282. PubMed PMID: 32664730.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Rhodium(III)-Catalyzed Direct Coupling of Quinoline-8-Carbaldehydes with (Het)Arylboronic Acids for the Synthesis of 8-Aryloylquinolines. AU - Lyu,Xue-Li, AU - Huang,Shi-Sheng, AU - Huang,Yuan-Qiong, AU - Li,Yong-Qiang, AU - Song,Hong-Jian, AU - Liu,Yu-Xiu, AU - Wang,Qing-Min, Y1 - 2020/07/28/ PY - 2020/7/16/pubmed PY - 2021/6/24/medline PY - 2020/7/16/entrez SP - 10271 EP - 10282 JF - The Journal of organic chemistry JO - J Org Chem VL - 85 IS - 15 N2 - 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 commercially available starting materials. Scale-up of the reaction and subsequent synthesis of tubulin polymerization inhibitor demonstrated its utilities. A plausible mechanism was proposed on the basis of the fact that a stable cycloacylrhodium intermediate complex could be used as catalyst, and the complex reacted stoichiometrically with (het)arylboronic acids. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/32664730/Rhodium_III__Catalyzed_Direct_Coupling_of_Quinoline_8_Carbaldehydes_with__Het_Arylboronic_Acids_for_the_Synthesis_of_8_Aryloylquinolines_ DB - PRIME DP - Unbound Medicine ER -