33757-48-1Relevant articles and documents
Site-specific: Ortho metallation via C-H bond activation and syntheses of ruthenium(III) organometallics: Studies on nitric oxide (NO) reactivity and photorelease of coordinated NO
Kumar, Rajan,Kumar, Sushil,Bala, Manju,Ratnam, Anand,Singh,Ghosh, Kaushik
, p. 72096 - 72106 (2016)
A new family of σ-aryl ruthenium(iii) complexes [Ru(L1-4)(PPh3)2Cl] (1-4) (where L1H2 = N-(quinolin-8-yl)benzamide for 1, L2H2 = 4-chloro-N-(quinolin-8-yl)benzamide for 2, L3H2 = 4-nitro-N-(quinolin-8-yl)benzamide for 3, L4H2 = 3-nitro-N-(quinolin-8-yl)benzamide for 4 and H = dissociable protons) derived from bidentate ligands having amide bonds was synthesized through C-H bond activation. These organometallic ruthenium(iii) complexes were treated with nitric oxide (NO) to afford the nitrosyl complexes [Ru(NO2L1-4)(PPh3)2(NO)](ClO4) (1a-4a) (where NO2L1H2 = N-(5-nitroquinolin-8-yl)benzamide for 1a, NO2L2H2 = 4-chloro-N-(5-nitroquinolin-8-yl)benzamide for 2a, NO2L3H2 = 4-nitro-N-(5-nitroquinolin-8-yl)benzamide for 3a, NO2L4H2 = 3-nitro-N-(5-nitroquinolin-8-yl)benzamide for 4a and H = dissociable protons). All ruthenium complexes were characterized by various spectroscopic techniques. An X-ray crystallographic study afforded the molecular structure of complex 4a and the site-specific orthometallation was scrutinized. The coordinated NO molecule was found to be photolabile under visible and UV light.
Palladium-Catalyzed ortho-Selective C-H Chlorination of Benzamide Derivatives under Anodic Oxidation Conditions
Konishi, Miki,Tsuchida, Kazuya,Sano, Katsuya,Kochi, Takuya,Kakiuchi, Fumitoshi
, p. 8716 - 8724 (2017)
The palladium-catalyzed ortho-selective chlorination of N-quinolinylbenzamide derivatives with hydrochloric acid was achieved under anodic oxidation conditions. The use of 5,7-dichloro-8-quinolinyl group as directing group was effective for the selective
Erratum: Catalytically Relevant Intermediates in the Ni-Catalyzed C(sp2)-H and C(sp3)-H Functionalization of Aminoquinoline Substrates (J. Am. Chem. Soc. (2019) 141:43 (17382-17387) DOI: 10.1021/jacs.9b09109)
Bour, James R.,Kampf, Jeff W.,Roy, Pronay,Sanford, Melanie S.
supporting information, p. 14021 - 14021 (2021/09/08)
Further analysis of our data revealed that the thermolysis ofNi(III) complex 4b does not lead to C(sp3)-N bondformingreductive elimination to form ?-lactam 3b-H. As such, our claim that this is “the first directly observable example of C(sp3)-N coupling from an isolated NiIII center” is incorrect. Equation 6 should be modified as follows: As a consequence, the statement in the Abstract that “a NiIII s-alkyl analogue underwent C(sp3)-N bond-forming reductive elimination at 140 °C in DMF to afford a ?-lactam product” is also incorrect. The TOC graphic should also be corrected as follows: After the discovery of this major error, we went back and carefully repeated all of the synthesis and reactivity experiments described in the Article to ensure their accuracy and reproducibility. This has led to changes in the yields and in some cases solvent and reaction time for many of the reactions reported therein. The Supporting Information has been updated with revised procedures and spectra as well as updated yields. In addition, we have included in the revised Supporting Information a copy of an updated manuscript with each change highlighted to clearly indicate these revisions. Unlike the error in eq 6, none of these additional changes alters our key conclusions from the original manuscript.FF
C-5 selective chlorination of 8-aminoquinoline amides using dichloromethane
Lin, Xinxin,Zeng, Cuilian,Liu, Chengkou,Fang, Zheng,Guo, Kai
supporting information, p. 1352 - 1357 (2021/02/26)
An oxidant-free electrochemical regioselective chlorination of 8-aminoquinoline amides at ambient temperature in batch and continuous-flow was achieved. Inert DCM was used as the chlorinating reagent. Owing to the continuous-flow setup, the reaction scale
Aryne Multicomponent Reactions by Directed C?H Activation
Sunnam, Sunil Kumar,Belani, Jitendra D.
supporting information, p. 8846 - 8850 (2021/05/31)
Arylation via ortho C?H activation by the aid of directing groups has been explored recently by many researchers. Herein, a palladium-catalyzed C?H arylation using 8-aminoquinoline as a bidentate directing group has been developed. The reaction furnishes only C?H arylation, unlike previous methods where cyclization to corresponding isoquinolones is observed. More interestingly, sequential C?H functionalization was observed when methylacrylate and acrylonitrile was added; this led to C?H olefination with the aryl group, which was installed from the aryne precursor.
