448211-45-8Relevant academic research and scientific papers
Development and Mechanistic Studies of Iron-Catalyzed Construction of Csp2-B Bonds via C-O Bond Activation
Geng, Shasha,Zhang, Juan,Chen, Shuo,Liu, Zhengli,Zeng, Xiaoqin,He, Yun,Feng, Zhang
, p. 5582 - 5588 (2020/07/08)
Herein we describe an iron-catalyzed borylation of alkenyl and aryl carbamates through the activation of a C-O bond. This protocol exhibits high efficiency, a broad substrate scope, and the late-stage borylation of biorelevant compounds, thus providing potential applications in medicinal chemistry. Moreover, this method enables orthogonal transformations of phenol derivatives and also offers good opportunities for the synthesis of multisubstituted arenes. Preliminary mechanistic studies suggest that a FeII/FeIII catalytic cycle via a radical pathway might be involved in the reaction.
Copper-catalyzed tri- or tetrafunctionalization of alkenylboronic acids to prepare tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles
Bi, Hong-Yan,Li, Cheng-Jing,Liang, Cui,Mo, Dong-Liang,Wei, Cui
, p. 5815 - 5821 (2020/09/21)
We describe a cascade strategy for tri- or tetrafunctionalization of alkenylboronic acids to prepare diverse tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles in good yields withN-hydroxybenzotriazin-4-one (HOOBT) and arylhydrazines as oxygen and nitrogen sources, respectively. Mechanistic studies reveal that the domino reaction undergoes the copper-catalyzed Chan-Lam reaction, [2,3]-rearrangement, nucleophilic substitution, oxidation and sequential [3,3]-rearrangement over five steps in a one-pot reaction. The reaction shows a broad substrate scope and tolerates a wide range of functional groups. More importantly, the reaction is easily performed at gram scales and the product is purified by simple extraction, washing, and recrystallization without flash column chromatography. The present protocol features easily available starting materials, high site-marked functionalization, five-step cascade in one pot, multiple C-C/C-O/C-N bond formation, and diversity of indole motifs.
Interrupted fischer-indole intermediates via oxyarylation of alkenyl boronic acids
Wang, Heng-Yen,Anderson, Laura L.
supporting information, p. 3362 - 3365 (2013/07/26)
The oxyarylation of alkenyl boronic acids with N-arylbenzhydroxamic acids has been achieved under both copper-mediated and copper-catalyzed conditions to provide access to interrupted Fischer-indole intermediates. This transformation is believed to proceed through a copper-promoted C-O bond forming event followed by a [3,3] rearrangement. The scope of the method is described and mechanistic experiments are discussed.
PSiP-pincer type palladium-catalyzed dehydrogenative borylation of alkenes and 1,3-Dienes
Kirai, Naohiro,Iguchi, Shoichiro,Ito, Tatsuyoshi,Takaya, Jun,Iwasawa, Nobuharu
, p. 784 - 799 (2013/08/23)
Dehydrogenative borylation of alkenes and 1,3-dienes was realized by carrying out the reaction in the presence of bis(pinacolato)diboron (B2pin2) and a catalytic amount of PSiP-pincer palladium complex. This protocol has the following notable features. 1)
Pushing the σ-donor strength in iridium pincer complexes: Bis(silylene) and bis(germylene) ligands are stronger donors than bis(phosphorus(III)) ligands
Brueck, Andreas,Gallego, Daniel,Wang, Wenyuan,Irran, Elisabeth,Driess, Matthias,Hartwig, John F.
supporting information, p. 11478 - 11482 (2013/01/15)
Breaking the donor limits: The remarkable coordination chemistry of ECHE (E=Si, Ge) ligands with Group-9 metals (Ir, Rh) and their application in catalytic C-H borylation of arenes was investigated. The spectroscopic and structural features of the first [ECE] iridium complexes show the stronger σ-donating properties of the divalent Si and Ge pincer ligands compared to analogous PIII-based ligands. Copyright
Efficient synthesis of diborylalkenes from alkenes and diboron by a new PSiP-pincer palladium-catalyzed dehydrogenative borylation
Takaya, Jun,Kirai, Naohiro,Iwasawa, Nobuharu
, p. 12980 - 12983 (2011/10/04)
The efficient synthesis of various diborylalkenes such as 1,1-, trans-1,2-, and cyclic 1,2-diborylalkenes from alkenes and diboron was achieved for the first time. Selective preparation of di- and monoborylalkenes was also realized by the appropriate choi
SPIROCYCLIC GPR40 MODULATORS
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Page/Page column 191, (2010/04/30)
The present invention provides compounds useful, for example, for treating metabolic disorders in a subject. Such compounds have the general formula IA, IB, I'A or I'B, where the definitions of the variables are provided herein. The present invention also
Rhodium-catalyzed dehydrogenative borylation of cyclic alkenes
Kondoh, Azusa,Jamison, Timothy F.
supporting information; experimental part, p. 907 - 909 (2010/06/12)
A rhodium-catalyzed dehydrogenative borylation of cyclic alkenes is described. This reaction provides direct access to cyclic 1-alkenylboronic acid pinacol esters, useful intermediates in organic synthesis. Suzuki-Miyaura cross-coupling applications are also presented. The Royal Society of Chemistry 2010.
CONFORMATIONALLY CONSTRAINED CARBOXYLIC ACID DERIVATIVES USEFUL FOR TREATING METABOLIC DISORDERS
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, (2009/10/22)
The present invention provides compounds useful, for example, for treating metabolic disorders in a subject. Such compounds have the general formula I or the general formula III: where the definitions of the variables are provided herein. The present invention also provides compositions that include, and methods for using, the compounds in preparing medicaments and for treating metabolic disorders such as, for example, type II diabetes.
Convenient preparation of cycloalkenyl boronic acid pinacol esters
Rauniyar, Vivek,Zhai, Huimin,Hall, Dennis G.
experimental part, p. 3984 - 3995 (2009/04/11)
A practical method for the preparation of cycloalkenyl boronic acid pinacol esters is described. These important synthetic intermediates are typically made using more expensive methods like transition metal-catalyzed borylation of alkenyl halides or trifl
