- Metal-Free C?H Borylation of N-Heteroarenes by Boron Trifluoride
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Organoboron compounds are essential reagents in modern C?C coupling reactions. Their synthesis via catalytic C?H borylation by main group elements is emerging as a powerful tool alternative to transition metal based catalysis. Herein, a straightforward metal-free synthesis of aryldifluoroboranes from BF3 and heteroarenes is reported. The reaction is assisted by sterically hindered amines and catalytic amounts of thioureas. According to computational studies the reaction proceeds via frustrated Lewis pair (FLP) mechanism. The obtained aryldifluoroboranes are further stabilized against destructive protodeborylation by converting them to the corresponding air stable tetramethylammonium organotrifluoroborates.
- Iashin, Vladimir,Berta, Dénes,Chernichenko, Konstantin,Nieger, Martin,Moslova, Karina,Pápai, Imre,Repo, Timo
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supporting information
p. 13873 - 13879
(2020/10/02)
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- The palladium-catalyzed direct C3-cyanation of indoles using acetonitrile as the cyanide source
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The ligand-free palladium-catalyzed C3-cyanation of indoles via direct C-H functionalization was achieved. This protocol, utilizing CH3CN as a green and readily available cyanide source, produced the desired products in moderate to good yields through transition-metal-catalyzed C-CN bond cleavage. This journal is
- Feng, Kejun,Li, Qiang,Li, Yuanhua,Liu, Bifu,Liu, Min,Zhou, Yongbo
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supporting information
p. 6108 - 6114
(2020/10/21)
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- Indole-3-carbonitriles as DYRK1A inhibitors by fragment-based drug design
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Dual-specificity tyrosine phosphorylation-regulated kinase 1A (DYRK1A) is a potential drug target because of its role in the development of Down syndrome and Alzheimer's disease. The selective DYRK1A inhibitor 10-iodo-11H-indolo[3, 2-c]quinoline-6-carboxy
- Meine, Rosanna,Becker, Walter,Falke, Hannes,Preu, Lutz,Loa?c, Nadège,Meijer, Laurent,Kunick, Conrad
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- Regiocontrolled Direct C?H Arylation of Indoles at the C4 and C5 Positions
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An effective and practical strategy has been established for the direct and site-selective arylation of indoles at the C4 and C5 positions with the aid of a readily accessible, cheap, and removable pivaloyl directing group at the C3 position. This transfo
- Yang, Youqing,Gao, Pan,Zhao, Yue,Shi, Zhuangzhi
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supporting information
p. 3966 - 3971
(2017/03/27)
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- On water phosphine-free palladium-catalyzed room temperature C-H arylation of indoles
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Get on top of your chemistry! An "on water", palladium-catalyzed, phosphine-free direct C-H arylation of indoles, with iodoarenes at 25-30°C, is disclosed (see scheme; TBDMS=N-tert-butyldimethylsilyl ether; SEM=N-2-(trimethylsilyl)ethoxymethyl; Bn=benzyl, Piv=pivabyl). The mildness of the reaction conditions permits the tolerance of a variety of N1-protected indoles.
- Islam, Saidul,Larrosa, Igor
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supporting information
p. 15093 - 15096
(2013/11/06)
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- Toward the enantioselective total synthesis of lyngbyatoxin A: On the stereocontrolled introduction of the quaternary stereogenic centre
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This paper deals with an approach to the enantioselective total synthesis of Lyngbyatoxin A, with focus on the stereocontrolled introduction of the quaternary stereogenic centre. The key step in the synthesis involves an enantiospecific Lewis-acid mediate
- T?nder, Janne E.,Tanner, David
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p. 6937 - 6945
(2007/10/03)
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- Substituted indole acid derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1)
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This invention provides compounds of the formula: wherein: X is a chemical bond, —CH2— or —C(O)—; R1 is alkyl, cycloalkyl, —CH2-cycloalkyl, pyridinyl, —CH2-pyridinyl, phenyl or benzyl; R2 is H, alkyl, cycloalkyl, —CH2-cycloalkyl, or perfluoroalkyl; R3 is H, halo, alkyl, perfluoroalkyl, alkoxy, cycloalkyl, —CH2-cycloalkyl, —NH2, or —NO2; R4 is optionally substituted phenyl, benzyl, benzyloxy, pyridinyl, or —CH2-pyridinyl, or the salt or ester forms thereof, as well as methods for using the compounds as inhibitors of plasminogen activator inhibitor-1 (PAI-1) and as therapeutic compositions for treating conditions resulting from fibrinolytic disorders such as deep vein thrombosis and coronary heart disease, and pulmonary fibrosis.
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- Radical cyclisation reactions of 7-bromoindoles
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The synthesis and radical cyclisation of 7-bromoindoles carrying an unsaturated N-alkyl group is described.
- Dobbs, Adrian P.,Jones, Keith,Veal, Ken T.
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p. 5379 - 5382
(2007/10/03)
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- Facile synthesis of 2-benzylindoles
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A wide range of 2-Benzylindoles 2 are conveniently and efficiently prepared by heating N-benzylindoles 1 in polyphosphoric acid. Mechanistic studies suggest an intramolecular rearrangement via the corresponding 3- benzyl intermediates.
- Wiedenau, Paul,Blechert, Siegfried
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p. 2033 - 2039
(2007/10/03)
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