77802-22-3Relevant academic research and scientific papers
Stepwise benzylic oxygenation via uranyl-photocatalysis
Hu, Deqing,Jiang, Xuefeng
supporting information, p. 124 - 129 (2022/01/19)
Stepwise oxygenation at the benzylic position (1°, 2°, 3°) of aromatic molecules was comprehensively established under ambient conditions via uranyl photocatalysis to produce carboxylic acids, ketones, and alcohols, respectively. The accuracy of the stepwise oxygenation was ensured by the tunability of catalytic activity in uranyl photocatalysis, which was adjusted by solvents and additives demonstrated through Stern–Volmer analysis. Hydrogen atom transfer between the benzylic position and the uranyl catalyst facilitated oxygenation, further confirmed by kinetic studies. Considerably improved efficiency of flow operation demonstrated the potential for industrial synthetic application.
Erratum: Ruthenium-catalyzed C-H hydroxylation in aqueous acid enables selective functionalization of amine derivatives (Journal of the American Chemical Society (2017) 139:28 (9503-9506) DOI: 10.1021/jacs.7b05469)
Mack, James B.C.,Gipson, John D.,Du Bois,Sigman, Matthew S.
supporting information, p. 3016 - 3016 (2021/03/01)
Page 9504. The structure of product 3cc in Table 2 was found to be mis-assigned. We thank Prof. Phil Baran and Dr. Rafael Navratil for bringing this error to our attention. The correct structure contains an additional benzylic alcohol at the C-9 position of the steroid (3cc′, shown below). With the accompanying change in molecular weight, the isolated yield is 29%. Supporting Information. The incorrect structure and yield also appeared on pages S20 and S84 in the SI. Given this, the HRMS entry on page S20 should read as follows: “HRMS (ESI-TOF) m/z calcd for C19H18F3O5S+ (M-O+Na)+ 415.0822, found 415.0857”. The complete corrected SI is provided here.
Direct α-Arylation of Alcohols with Aryl Halides through a Radical Chain Mechanism
Aoki, Kohei,Yonekura, Kyohei,Ikeda, Yuko,Ueno, Ryota,Shirakawa, Eiji
supporting information, p. 2200 - 2204 (2020/05/05)
Alcohols were found to be arylated directly at their α-C?H bond with aryl halides in the presence of a base and a substoichiometric amount of t-BuOOt-Bu through a homolytic aromatic substitution mechanism. (Figure presented.).
POSITIVE ALLOSTERIC MODULATORS OF THE MUSCARINIC ACETYLCHOLINE RECEPTOR M4
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Paragraph 0446; 0447, (2019/06/14)
Disclosed herein are tricyclic compounds, including thieno[2,3-d:4,5-d′]dipyrimidin-4-amine and pyrido[4′,3′:4,5]thieno[2,3-d]pyrimidin-8-amine compounds, which may be useful as positive allosteric modulators of the muscarinic acetylcholine receptor Msub
POSITIVE ALLOSTERIC MODULATORS OF THE MUSCARINIC ACETYLCHOLINE RECEPTOR M4
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Paragraph 00228-00229, (2019/06/23)
Disclosed herein are tricyclic compounds, including 3-(difluoromethyl)-4-methylpyrimido[4',5':4,5]thieno[2,3-c]pyridazin-8-amine compounds, which may be useful as positive allosteric modulators of the muscarinic acetylcholine receptor M4 (mAChR
Oxidation of Tertiary Aromatic Alcohols to Ketones in Water
Chen, Dengfeng,Zhang, Yuchen,Pan, Xingyu,Wang, Fei,Huang, Shenlin
supporting information, p. 3607 - 3612 (2018/09/18)
A new rosin-based amphiphile enables the oxidation of tertiary aromatic alcohols in water under mild conditions. The oxidation process is mediated by β-scission of alkoxy radicals. Our catalyst system including the surfactant, catalysts, and water can be easily recycled within the same reaction vial. (Figure presented.).
POSITIVE ALLOSTERIC MODULATORS OF THE MUSCARINIC ACETYLCHOLINE RECEPTOR M4
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Paragraph 00238, (2018/05/24)
Disclosed herein are pyrido[3',2':4,5]thieno[2,3-d]pyridazin-8-amine and thieno[2,3-c:4,5-d']dipyridazin-8-amine compounds, which may be useful as positive allosteric modulators of the muscarinic acetylcholine receptor M4 (mAChR M4).
POSITIVE ALLOSTERIC MODULATORS OF THE MUSCARINIC ACETYLCHOLINE RECEPTOR M4
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Paragraph 00220; 00221, (2018/05/24)
Disclosed herein are thieno[2,3-b:5,4-c']dipyridin-8-amine and pyrido[4',3':4,5]thieno[2,3-c]pyridazin-8-amine compounds, which may be useful as positive allosteric modulators of the muscarinic acetylcholine receptor M4 (mAChR M4). A
POSITIVE ALLOSTERIC MODULATORS OF THE MUSCARINIC ACETYLCHOLINE RECEPTOR M4
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Paragraph 00216; 00217, (2018/07/05)
Disclosed herein are 2,4-dimethylquinoline-6-carboxamide compounds and 3,4- dimethylcinnoline-6-carboxamide compounds, which may be useful as positive allosteric modulators of the muscarinic acetylcholine receptor M4(mAChR M4). Also disclosed herein are methods of making the compounds, pharmaceutical compositions comprising the compounds, and methods of treating neurological and psychiatric disorders associated with muscarinic acetylcholine receptor dysfunction using the compounds and compositions.
Ruthenium-Catalyzed C-H Hydroxylation in Aqueous Acid Enables Selective Functionalization of Amine Derivatives
Mack, James B. C.,Gipson, John D.,Du Bois,Sigman, Matthew S.
supporting information, p. 9503 - 9506 (2017/07/24)
The identification, optimization, and evaluation of a new catalytic protocol for sp3 C-H hydroxylation is described. Reactions are performed in aqueous acid using a bis(bipyridine)Ru catalyst to enable oxidation of substrates possessing basic amine functional groups. Tertiary and benzylic C-H hydroxylation is strongly favored over N-oxidation for numerous amine derivatives. With terpene-derived substrates, similar trends in reactivity toward tertiary and benzylic C-H bonds are observed. Hydroxylation of chiral tertiary centers is enantiospecific in spite of the ionizing strength of the reaction medium. Preliminary kinetics experiments show a marked difference in reactivity between isomeric cis- and trans-Ru catalysts suggesting that the catalyst is configurationally stable under the reaction conditions.
