Comparison of Imine to Olefin Insertion Reactions: Generation of Five- and Six-Membered Lactams via a Nickel-Mediated CO, Olefin, CO, Imine Insertion Cascade

Davis, Jason L.; Arndtsen, Bruce A.

doi:10.1021/om1011566

Cited by 9 publications

(2 citation statements)

References 45 publications

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“…Nickel bipyridine complexes have played a significant role in synthetic chemistry. Much of the fundamental information regarding reductive elimination processes, − redox events, ,,− insertion reactions, − polymer synthesis, − and electrocatalytic couplings − using nickel comes from studies initiated with complexes bearing the bipyridine ligand. With the explosion of interest in synthesizing organic molecules bearing perfluoroalkyl functional groups, − we became interested in preparing nickel bipyridine complexes bearing two perfluoroalkyl ligands in order to compare and contrast the reactivity with that known for nickel bipyridine dialkyl complexes.…”

Section: Introductionmentioning

confidence: 99%

Linear Bis(perfluoroalkyl) Complexes of Nickel Bipyridine

et al. 2012

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Section: Introductionmentioning

confidence: 99%

Linear Bis(perfluoroalkyl) Complexes of Nickel Bipyridine

et al. 2012

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“…Those are probably due to the morphological difference of each cavity of the host CDs. Partly, primary amines at Et‐β‐CD can undergo nucleophilic addition with ketones of QUE to give carbinolamines which then dehydrate to result in substituted imines, and the possibility of imine formation can be proved by 1 H, 13 C‐HMBC, NMR, FT‐IR, and Raman spectroscopy . However, the major component in solution is attributed to the complex as shown in cross peaks between B ring of QUE and inner cavity of Et‐β‐CD (Figure ), and it is accordance with the molecular modeling data of the complex in Figure .…”

Section: Resultsmentioning

confidence: 99%

Enhancement of Solubility and Bioavailability of Quercetin by Inclusion Complexation with the Cavity of Mono‐6‐deoxy‐6‐aminoethylamino‐β‐cyclodextrin

Park

Choi

Cho

et al. 2017

Bulletin Korean Chem Soc

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Quercetin (QUE) has a wide range of health benefits; however, its application is limited due to its low solubility. We synthesized mono-6-deoxy-6-aminoethylamino-β-cyclodextrin (Et-β-CD) to overcome this limitation. The solubility of QUE was increased 35.1-fold compared with QUE, by its complexation with Et-β-CD. Changes in physicochemical properties following successful complexation were investigated using field emission scanning electron microscope, differential scanning calorimetry, and Fourier transform infrared spectroscopy. The complexation behavior of QUE and Et-β-CD in aqueous solution was monitored by 1 H nuclear magnetic resonance (NMR), 2D rotating frame nuclear overhauser, and diffusion-ordered spectroscopy. The molecular docking simulation showed that the oblong shaped QUE is suitable for the formation of a stable complex with a characteristic cavity of Et-β-CD. Furthermore, the antioxidant activity and photostability of QUE was also improved after its complexation with Et-β-CD. From these results, we suggest that the characteristic elliptical cavity of Et-β-CD can be utilized for other hardly soluble drug molecules, which can expand the development of drug delivery systems.

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Forming Benzylic Iodides via a Nickel Catalyzed Diastereoselective Dearomative Carboiodination Reaction of Indoles

et al. 2019

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Ad iastereoselective dearomative carboiodination reaction is reported. We report an ovel metal-catalyzed approach to install reactive secondary benzylic iodides. Utilizing the unique reactivity of nickel, we have expanded the carboiodination reaction to non-activated aromatic double bonds forming ap reviously unattainable class of iodides.W e also report ab roadly applicable method to avoid the use of ametallic reducing agent by utilizing an alkylphosphite as the ligand. The reaction is thought to proceed through as yn intramolecular carbonickelation across a2 -substituted indole followed by ad iastereoretentive reductive elimination of the carbonÀiodine bond. The complex iodinated indolines generated in the reaction were obtained in moderate to good yields and good to excellent diastereoselectivity.T he products were easily functionalized by av ariety of synthetic methods.

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Comparison of Imine to Olefin Insertion Reactions: Generation of Five- and Six-Membered Lactams via a Nickel-Mediated CO, Olefin, CO, Imine Insertion Cascade

Cited by 9 publications

References 45 publications

Linear Bis(perfluoroalkyl) Complexes of Nickel Bipyridine

Linear Bis(perfluoroalkyl) Complexes of Nickel Bipyridine

Enhancement of Solubility and Bioavailability of Quercetin by Inclusion Complexation with the Cavity of Mono‐6‐deoxy‐6‐aminoethylamino‐β‐cyclodextrin

Forming Benzylic Iodides via a Nickel Catalyzed Diastereoselective Dearomative Carboiodination Reaction of Indoles

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