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Direct C-H alkylation and indole formation of anilines with diazo compounds under rhodium catalysis.

Chemical communications (Cambridge, England)

Mishra NK, Choi M, Jo H, Oh Y, Sharma S, Han SH, Jeong T, Han S, Lee SY, Kim IS.
PMID: 26458276
Chem Commun (Camb). 2015 Dec 18;51(97):17229-32. doi: 10.1039/c5cc07767b.

The rhodium(III)-catalyzed direct functionalization of aniline C-H bonds with α-diazo compounds is described. These transformations provide a facile construction of ortho-alkylated anilines with diazo malonates or highly substituted indoles with diazo acetoacetates.

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Mishra NK, Choi M, Jo H, et al. Direct C-H alkylation and indole formation of anilines with diazo compounds under rhodium catalysis. Chem Commun (Camb). 2015;51(97):17229-32doi: 10.1039/c5cc07767b.
Mishra, N. K., Choi, M., Jo, H., Oh, Y., Sharma, S., Han, S. H., Jeong, T., Han, S., Lee, S. Y., & Kim, I. S. (2015). Direct C-H alkylation and indole formation of anilines with diazo compounds under rhodium catalysis. Chemical communications (Cambridge, England), 51(97), 17229-32. https://doi.org/10.1039/c5cc07767b
Mishra, Neeraj Kumar, et al. "Direct C-H alkylation and indole formation of anilines with diazo compounds under rhodium catalysis." Chemical communications (Cambridge, England) vol. 51,97 (2015): 17229-32. doi: https://doi.org/10.1039/c5cc07767b
Mishra NK, Choi M, Jo H, Oh Y, Sharma S, Han SH, Jeong T, Han S, Lee SY, Kim IS. Direct C-H alkylation and indole formation of anilines with diazo compounds under rhodium catalysis. Chem Commun (Camb). 2015 Dec 18;51(97):17229-32. doi: 10.1039/c5cc07767b. PMID: 26458276.
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Synthesis of a bulky and electron-rich derivative of SEGPhos and its application in Ru-catalyzed enantioselective hydrogenation of beta-ketoesters.

The Journal of organic chemistry

Wan X, Sun Y, Luo Y, Li D, Zhang Z.
PMID: 15675874
J Org Chem. 2005 Feb 04;70(3):1070-2. doi: 10.1021/jo048466d.

The synthesis and resolution of a bulky and electron-rich derivative of SEGPhos and its application in Ru-catalyzed asymmetric hydrogenation reaction of beta-ketoesters are reported. Up to 99.5% ee was achieved. Under solvent-free reaction conditions, acetoacetates could be reduced with...

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Wan X, Sun Y, Luo Y, et al. Synthesis of a bulky and electron-rich derivative of SEGPhos and its application in Ru-catalyzed enantioselective hydrogenation of beta-ketoesters. J Org Chem. 2005;70(3):1070-2doi: 10.1021/jo048466d.
Wan, X., Sun, Y., Luo, Y., Li, D., & Zhang, Z. (2005). Synthesis of a bulky and electron-rich derivative of SEGPhos and its application in Ru-catalyzed enantioselective hydrogenation of beta-ketoesters. The Journal of organic chemistry, 70(3), 1070-2. https://doi.org/10.1021/jo048466d
Wan, Xiaobing, et al. "Synthesis of a bulky and electron-rich derivative of SEGPhos and its application in Ru-catalyzed enantioselective hydrogenation of beta-ketoesters." The Journal of organic chemistry vol. 70,3 (2005): 1070-2. doi: https://doi.org/10.1021/jo048466d
Wan X, Sun Y, Luo Y, Li D, Zhang Z. Synthesis of a bulky and electron-rich derivative of SEGPhos and its application in Ru-catalyzed enantioselective hydrogenation of beta-ketoesters. J Org Chem. 2005 Feb 04;70(3):1070-2. doi: 10.1021/jo048466d. PMID: 15675874.
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Organocatalytic Asymmetric Biginelli-like Reaction Involving Isatin.

The Journal of organic chemistry

Stucchi M, Lesma G, Meneghetti F, Rainoldi G, Sacchetti A, Silvani A.
PMID: 26836474
J Org Chem. 2016 Mar 04;81(5):1877-84. doi: 10.1021/acs.joc.5b02680. Epub 2016 Feb 12.

The first asymmetric, Brønsted acid catalyzed Biginelli-like reaction of a ketone has been developed, employing N-substituted isatins as carbonyl substrates, and urea and alkyl acetoacetates as further components. BINOL-derived phosphoric acid catalysts have been used to achieve the synthesis...

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Stucchi M, Lesma G, Meneghetti F, et al. Organocatalytic Asymmetric Biginelli-like Reaction Involving Isatin. J Org Chem. 2016;81(5):1877-84doi: 10.1021/acs.joc.5b02680.
Stucchi, M., Lesma, G., Meneghetti, F., Rainoldi, G., Sacchetti, A., & Silvani, A. (2016). Organocatalytic Asymmetric Biginelli-like Reaction Involving Isatin. The Journal of organic chemistry, 81(5), 1877-84. https://doi.org/10.1021/acs.joc.5b02680
Stucchi, Mattia, et al. "Organocatalytic Asymmetric Biginelli-like Reaction Involving Isatin." The Journal of organic chemistry vol. 81,5 (2016): 1877-84. doi: https://doi.org/10.1021/acs.joc.5b02680
Stucchi M, Lesma G, Meneghetti F, Rainoldi G, Sacchetti A, Silvani A. Organocatalytic Asymmetric Biginelli-like Reaction Involving Isatin. J Org Chem. 2016 Mar 04;81(5):1877-84. doi: 10.1021/acs.joc.5b02680. Epub 2016 Feb 12. PMID: 26836474.
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Organocatalysis by Networks of Cooperative Hydrogen Bonds: Enantioselective Direct Mannich Addition to Preformed Arylideneureas.

Angewandte Chemie (International ed. in English)

Lillo VJ, Mansilla J, Saá JM.
PMID: 26918408
Angew Chem Int Ed Engl. 2016 Mar 18;55(13):4312-6. doi: 10.1002/anie.201511555. Epub 2016 Feb 25.

The concept of noncovalent organocatalysis by means of networks of cooperative hydrogen bonds (NCHB organocatalysis) has been explored. Arylideneureas were chosen as ideal substrates because of their powerful donor-acceptor properties. We have examined their uncatalyzed, direct Mannich reaction with...

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Lillo VJ, Mansilla J, Saá JM. Organocatalysis by Networks of Cooperative Hydrogen Bonds: Enantioselective Direct Mannich Addition to Preformed Arylideneureas. Angew Chem Int Ed Engl. 2016;55(13):4312-6doi: 10.1002/anie.201511555.
Lillo, V. J., Mansilla, J., & Saá, J. M. (2016). Organocatalysis by Networks of Cooperative Hydrogen Bonds: Enantioselective Direct Mannich Addition to Preformed Arylideneureas. Angewandte Chemie (International ed. in English), 55(13), 4312-6. https://doi.org/10.1002/anie.201511555
Lillo, Victor J, et al. "Organocatalysis by Networks of Cooperative Hydrogen Bonds: Enantioselective Direct Mannich Addition to Preformed Arylideneureas." Angewandte Chemie (International ed. in English) vol. 55,13 (2016): 4312-6. doi: https://doi.org/10.1002/anie.201511555
Lillo VJ, Mansilla J, Saá JM. Organocatalysis by Networks of Cooperative Hydrogen Bonds: Enantioselective Direct Mannich Addition to Preformed Arylideneureas. Angew Chem Int Ed Engl. 2016 Mar 18;55(13):4312-6. doi: 10.1002/anie.201511555. Epub 2016 Feb 25. PMID: 26918408.
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Synthesis of Mono- and Bis(fluoroalkyl)pyrimidines from FARs, Fluorinated Acetoacetates, and Malononitrile Provides Easy Access to Novel High-Value Pyrimidine Scaffolds.

Chemistry (Weinheim an der Bergstrasse, Germany)

Schmitt E, Commare B, Panossian A, Vors JP, Pazenok S, Leroux FR.
PMID: 28992385
Chemistry. 2018 Jan 26;24(6):1311-1316. doi: 10.1002/chem.201703982. Epub 2017 Nov 23.

A new strategy was developed using fluorinated acetoacetates, malononitrile, and fluoroalkyl amino reagents (FARs) to access unprecedented 4,6-bis(fluoroalkyl)pyrimidine-5-carboxylates, their carboxylic acid analogues, and 4-amino-6-(fluoroalkyl)pyrimidine-5-carbonitriles. An efficient cyclization step using suitable amidines was developed under microwave irradiation, providing the desired...

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Schmitt E, Commare B, Panossian A, et al. Synthesis of Mono- and Bis(fluoroalkyl)pyrimidines from FARs, Fluorinated Acetoacetates, and Malononitrile Provides Easy Access to Novel High-Value Pyrimidine Scaffolds. Chemistry. 2017;24(6):1311-1316doi: 10.1002/chem.201703982.
Schmitt, E., Commare, B., Panossian, A., Vors, J. P., Pazenok, S., & Leroux, F. R. (2018). Synthesis of Mono- and Bis(fluoroalkyl)pyrimidines from FARs, Fluorinated Acetoacetates, and Malononitrile Provides Easy Access to Novel High-Value Pyrimidine Scaffolds. Chemistry (Weinheim an der Bergstrasse, Germany), 24(6), 1311-1316. https://doi.org/10.1002/chem.201703982
Schmitt, Etienne, et al. "Synthesis of Mono- and Bis(fluoroalkyl)pyrimidines from FARs, Fluorinated Acetoacetates, and Malononitrile Provides Easy Access to Novel High-Value Pyrimidine Scaffolds." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 24,6 (2018): 1311-1316. doi: https://doi.org/10.1002/chem.201703982
Schmitt E, Commare B, Panossian A, Vors JP, Pazenok S, Leroux FR. Synthesis of Mono- and Bis(fluoroalkyl)pyrimidines from FARs, Fluorinated Acetoacetates, and Malononitrile Provides Easy Access to Novel High-Value Pyrimidine Scaffolds. Chemistry. 2018 Jan 26;24(6):1311-1316. doi: 10.1002/chem.201703982. Epub 2017 Nov 23. PMID: 28992385.
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Organocatalytic cascade reactions based on push-pull dienamine platform: synthesis of highly substituted anilines.

The Journal of organic chemistry

Ramachary DB, Ramakumar K, Narayana VV.
PMID: 17288390
J Org Chem. 2007 Feb 16;72(4):1458-63. doi: 10.1021/jo0623639.

A practical and novel one-pot organocatalytic selective process for the cascade synthesis of highly substituted o-hydroxydiarylamines and o-pyrrolidin-1-yldiarylamines is reported. Direct combination of amine-catalyzed cascade Knoevenagel/Michael/aldol condensation/decarboxylation and cascade enamine amination/isoaromatization of alkyl acetoacetates, aldehydes, and nitrosoarenes furnished the...

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Ramachary DB, Ramakumar K, Narayana VV. Organocatalytic cascade reactions based on push-pull dienamine platform: synthesis of highly substituted anilines. J Org Chem. 2007;72(4):1458-63doi: 10.1021/jo0623639.
Ramachary, D. B., Ramakumar, K., & Narayana, V. V. (2007). Organocatalytic cascade reactions based on push-pull dienamine platform: synthesis of highly substituted anilines. The Journal of organic chemistry, 72(4), 1458-63. https://doi.org/10.1021/jo0623639
Ramachary, Dhevalapally B, et al. "Organocatalytic cascade reactions based on push-pull dienamine platform: synthesis of highly substituted anilines." The Journal of organic chemistry vol. 72,4 (2007): 1458-63. doi: https://doi.org/10.1021/jo0623639
Ramachary DB, Ramakumar K, Narayana VV. Organocatalytic cascade reactions based on push-pull dienamine platform: synthesis of highly substituted anilines. J Org Chem. 2007 Feb 16;72(4):1458-63. doi: 10.1021/jo0623639. PMID: 17288390.
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Showing 1 to 6 of 6 entries