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Ruthenium-catalyzed oxidative coupling/cyclization of isoquinolones with alkynes through C-H/N-H activation: mechanism study and synthesis of dibenzo[a,g]quinolizin-8-one derivatives.
Chemistry. 2012 Oct 01; 18(40):12873-9.C

Abstract

The mechanism of [{RuCl(2)(p-cymene)}(2)]-catalyzed oxidative annulations of isoquinolones with alkynes was investigated in detail. The first step is an acetate-assisted C-H bond activation process to form cyclometalated compounds. Subsequent mono-alkyne insertion of the Ru-C bonds of the cyclometalated compounds then takes place. Finally, oxidative coupling of the C-N bond of the insertion compounds occurs to afford Ru(0) sandwich complexes that undergo oxidation to regenerate the catalytically active Ru(II) complex with the copper oxidant and release the desired dibenzo[a,g]quinolizin-8-one derivatives. All of the relevant intermediates were fully characterized and determined by single crystal X-ray diffraction analysis. The [{RuCl(2)(p-cymene)}(2)]-catalyzed C-H bond functionalization of isoquinolones with alkynes to synthesize dibenzo[a,g]quinolizin-8-one derivatives through C-H/N-H activation was also demonstrated.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Li B
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, PR China. nklibin@nankai.edu.cn
Feng H
No affiliation info available
Wang N
No affiliation info available
Ma J
No affiliation info available
Song H
No affiliation info available
Xu S
No affiliation info available
Wang B
No affiliation info available

MeSH

AlkynesCatalysisCrystallography, X-RayCyclizationIsoquinolinesMolecular StructureOrganometallic CompoundsOxidation-ReductionQuinolizinesRuthenium

Pub Type(s)

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

Language

eng

PubMed ID

22930580

Citation

Li, Bin, et al. "Ruthenium-catalyzed Oxidative Coupling/cyclization of Isoquinolones With Alkynes Through C-H/N-H Activation: Mechanism Study and Synthesis of Dibenzo[a,g]quinolizin-8-one Derivatives." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 18, no. 40, 2012, pp. 12873-9.
Li B, Feng H, Wang N, et al. Ruthenium-catalyzed oxidative coupling/cyclization of isoquinolones with alkynes through C-H/N-H activation: mechanism study and synthesis of dibenzo[a,g]quinolizin-8-one derivatives. Chemistry. 2012;18(40):12873-9.
Li, B., Feng, H., Wang, N., Ma, J., Song, H., Xu, S., & Wang, B. (2012). Ruthenium-catalyzed oxidative coupling/cyclization of isoquinolones with alkynes through C-H/N-H activation: mechanism study and synthesis of dibenzo[a,g]quinolizin-8-one derivatives. Chemistry (Weinheim an Der Bergstrasse, Germany), 18(40), 12873-9. https://doi.org/10.1002/chem.201201862
Li B, et al. Ruthenium-catalyzed Oxidative Coupling/cyclization of Isoquinolones With Alkynes Through C-H/N-H Activation: Mechanism Study and Synthesis of Dibenzo[a,g]quinolizin-8-one Derivatives. Chemistry. 2012 Oct 1;18(40):12873-9. PubMed PMID: 22930580.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Ruthenium-catalyzed oxidative coupling/cyclization of isoquinolones with alkynes through C-H/N-H activation: mechanism study and synthesis of dibenzo[a,g]quinolizin-8-one derivatives. AU - Li,Bin, AU - Feng,Huiliang, AU - Wang,Nuancheng, AU - Ma,Jianfeng, AU - Song,Haibin, AU - Xu,Shansheng, AU - Wang,Baiquan, Y1 - 2012/08/28/ PY - 2012/05/28/received PY - 2012/8/30/entrez PY - 2012/8/30/pubmed PY - 2013/4/6/medline SP - 12873 EP - 9 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 18 IS - 40 N2 - The mechanism of [{RuCl(2)(p-cymene)}(2)]-catalyzed oxidative annulations of isoquinolones with alkynes was investigated in detail. The first step is an acetate-assisted C-H bond activation process to form cyclometalated compounds. Subsequent mono-alkyne insertion of the Ru-C bonds of the cyclometalated compounds then takes place. Finally, oxidative coupling of the C-N bond of the insertion compounds occurs to afford Ru(0) sandwich complexes that undergo oxidation to regenerate the catalytically active Ru(II) complex with the copper oxidant and release the desired dibenzo[a,g]quinolizin-8-one derivatives. All of the relevant intermediates were fully characterized and determined by single crystal X-ray diffraction analysis. The [{RuCl(2)(p-cymene)}(2)]-catalyzed C-H bond functionalization of isoquinolones with alkynes to synthesize dibenzo[a,g]quinolizin-8-one derivatives through C-H/N-H activation was also demonstrated. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/22930580/Ruthenium_catalyzed_oxidative_coupling/cyclization_of_isoquinolones_with_alkynes_through_C_H/N_H_activation:_mechanism_study_and_synthesis_of_dibenzo[ag]quinolizin_8_one_derivatives_ DB - PRIME DP - Unbound Medicine ER -