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Synthesis of Arylamines via Aminium Radicals.

Angewandte Chemie (International ed. in English)

Svejstrup TD, Ruffoni A, Juliá F, Aubert VM, Leonori D.
PMID: 28967171
Angew Chem Int Ed Engl. 2017 Nov 20;56(47):14948-14952. doi: 10.1002/anie.201708693. Epub 2017 Oct 24.

Arylamines constitute the core structure of many therapeutic agents, agrochemicals, and organic materials. The development of methods for the efficient and selective construction of these structural motifs from simple building blocks is desirable but still challenging. We demonstrate that...

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Svejstrup TD, Ruffoni A, Juliá F, et al. Synthesis of Arylamines via Aminium Radicals. Angew Chem Int Ed Engl. 2017;56(47):14948-14952doi: 10.1002/anie.201708693.
Svejstrup, T. D., Ruffoni, A., Juliá, F., Aubert, V. M., & Leonori, D. (2017). Synthesis of Arylamines via Aminium Radicals. Angewandte Chemie (International ed. in English), 56(47), 14948-14952. https://doi.org/10.1002/anie.201708693
Svejstrup, Thomas D, et al. "Synthesis of Arylamines via Aminium Radicals." Angewandte Chemie (International ed. in English) vol. 56,47 (2017): 14948-14952. doi: https://doi.org/10.1002/anie.201708693
Svejstrup TD, Ruffoni A, Juliá F, Aubert VM, Leonori D. Synthesis of Arylamines via Aminium Radicals. Angew Chem Int Ed Engl. 2017 Nov 20;56(47):14948-14952. doi: 10.1002/anie.201708693. Epub 2017 Oct 24. PMID: 28967171; PMCID: PMC5698739.
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Brønsted Acid Catalyzed Nitrile Synthesis from Aldehydes Using Oximes via Transoximation at Ambient Temperature.

Organic letters

Hyodo K, Togashi K, Oishi N, Hasegawa G, Uchida K.
PMID: 28513166
Org Lett. 2017 Jun 02;19(11):3005-3008. doi: 10.1021/acs.orglett.7b01263. Epub 2017 May 17.

The Brønsted acid-catalyzed synthesis of nitriles is described via transoximation under mild conditions using an O-protected oxime as a more stable equivalent of explosive O-protected hydroxylamines. The nitrile was generated via an O-protected aldoxime produced from the aldehyde and...

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Hyodo K, Togashi K, Oishi N, et al. Brønsted Acid Catalyzed Nitrile Synthesis from Aldehydes Using Oximes via Transoximation at Ambient Temperature. Org Lett. 2017;19(11):3005-3008doi: 10.1021/acs.orglett.7b01263.
Hyodo, K., Togashi, K., Oishi, N., Hasegawa, G., & Uchida, K. (2017). Brønsted Acid Catalyzed Nitrile Synthesis from Aldehydes Using Oximes via Transoximation at Ambient Temperature. Organic letters, 19(11), 3005-3008. https://doi.org/10.1021/acs.orglett.7b01263
Hyodo, Kengo, et al. "Brønsted Acid Catalyzed Nitrile Synthesis from Aldehydes Using Oximes via Transoximation at Ambient Temperature." Organic letters vol. 19,11 (2017): 3005-3008. doi: https://doi.org/10.1021/acs.orglett.7b01263
Hyodo K, Togashi K, Oishi N, Hasegawa G, Uchida K. Brønsted Acid Catalyzed Nitrile Synthesis from Aldehydes Using Oximes via Transoximation at Ambient Temperature. Org Lett. 2017 Jun 02;19(11):3005-3008. doi: 10.1021/acs.orglett.7b01263. Epub 2017 May 17. PMID: 28513166.
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Fe-catalyzed synthesis of substituted N-aryl oxazolidines.

Organic & biomolecular chemistry

Murru S, Lott CS, McGough B, Bernard DM, Srivastava RS.
PMID: 27001918
Org Biomol Chem. 2016 Apr 12;14(15):3681-5. doi: 10.1039/c6ob00185h.

A novel iron-catalyzed synthesis of substituted N-aryl oxazolidines was developed via C-N bond formation and methylenation. The reaction of aryl hydroxylamines with allyl alcohols, in the presence of formaldehyde or its equivalents, afforded variety of oxazolidine heterocycles in very...

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Murru S, Lott CS, McGough B, et al. Fe-catalyzed synthesis of substituted N-aryl oxazolidines. Org Biomol Chem. 2016;14(15):3681-5doi: 10.1039/c6ob00185h.
Murru, S., Lott, C. S., McGough, B., Bernard, D. M., & Srivastava, R. S. (2016). Fe-catalyzed synthesis of substituted N-aryl oxazolidines. Organic & biomolecular chemistry, 14(15), 3681-5. https://doi.org/10.1039/c6ob00185h
Murru, Siva, et al. "Fe-catalyzed synthesis of substituted N-aryl oxazolidines." Organic & biomolecular chemistry vol. 14,15 (2016): 3681-5. doi: https://doi.org/10.1039/c6ob00185h
Murru S, Lott CS, McGough B, Bernard DM, Srivastava RS. Fe-catalyzed synthesis of substituted N-aryl oxazolidines. Org Biomol Chem. 2016 Apr 12;14(15):3681-5. doi: 10.1039/c6ob00185h. PMID: 27001918.
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Dehydrogenative TEMPO-Mediated Formation of Unstable Nitrones: Easy Access to N-Carbamoyl Isoxazolines.

Chemistry (Weinheim an der Bergstrasse, Germany)

Gini A, Segler M, Kellner D, Mancheño OG.
PMID: 26212677
Chemistry. 2015 Aug 17;21(34):12053-60. doi: 10.1002/chem.201501314. Epub 2015 Jul 17.

N-carbamoyl nitrones represent an important class of reagents for the synthesis of a variety of natural and biologically active compounds. These compounds are generally converted into valuable 4-isoxazolines upon cyclization reaction with dipolarophiles. However, these types of N-protected nitrones...

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Gini A, Segler M, Kellner D, et al. Dehydrogenative TEMPO-Mediated Formation of Unstable Nitrones: Easy Access to N-Carbamoyl Isoxazolines. Chemistry. 2015;21(34):12053-60doi: 10.1002/chem.201501314.
Gini, A., Segler, M., Kellner, D., & Mancheño, O. G. (2015). Dehydrogenative TEMPO-Mediated Formation of Unstable Nitrones: Easy Access to N-Carbamoyl Isoxazolines. Chemistry (Weinheim an der Bergstrasse, Germany), 21(34), 12053-60. https://doi.org/10.1002/chem.201501314
Gini, Andrea, et al. "Dehydrogenative TEMPO-Mediated Formation of Unstable Nitrones: Easy Access to N-Carbamoyl Isoxazolines." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,34 (2015): 12053-60. doi: https://doi.org/10.1002/chem.201501314
Gini A, Segler M, Kellner D, Mancheño OG. Dehydrogenative TEMPO-Mediated Formation of Unstable Nitrones: Easy Access to N-Carbamoyl Isoxazolines. Chemistry. 2015 Aug 17;21(34):12053-60. doi: 10.1002/chem.201501314. Epub 2015 Jul 17. PMID: 26212677.
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Organocatalyzed Multicomponent Synthesis of Isoxazolidin-5-ones.

Organic letters

Berini C, Sebban M, Oulyadi H, Sanselme M, Levacher V, Brière JF.
PMID: 26488447
Org Lett. 2015 Nov 06;17(21):5408-11. doi: 10.1021/acs.orglett.5b02755. Epub 2015 Oct 21.

An unprecedented multicomponent organocatalyzed Knoevenagel-aza-Michael-cyclocondensation reaction between Meldrum's acid, hydroxylamines, and aldehydes afforded a straightforward entry to a large array of racemic and syn-diastereoenriched isoxazolidinones as synthetically useful scaffolds. This process revealed a markedly facile aza-Michael-cyclocondensation sequence as a...

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Berini C, Sebban M, Oulyadi H, et al. Organocatalyzed Multicomponent Synthesis of Isoxazolidin-5-ones. Org Lett. 2015;17(21):5408-11doi: 10.1021/acs.orglett.5b02755.
Berini, C., Sebban, M., Oulyadi, H., Sanselme, M., Levacher, V., & Brière, J. F. (2015). Organocatalyzed Multicomponent Synthesis of Isoxazolidin-5-ones. Organic letters, 17(21), 5408-11. https://doi.org/10.1021/acs.orglett.5b02755
Berini, Christophe, et al. "Organocatalyzed Multicomponent Synthesis of Isoxazolidin-5-ones." Organic letters vol. 17,21 (2015): 5408-11. doi: https://doi.org/10.1021/acs.orglett.5b02755
Berini C, Sebban M, Oulyadi H, Sanselme M, Levacher V, Brière JF. Organocatalyzed Multicomponent Synthesis of Isoxazolidin-5-ones. Org Lett. 2015 Nov 06;17(21):5408-11. doi: 10.1021/acs.orglett.5b02755. Epub 2015 Oct 21. PMID: 26488447.
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Synthesis of chemically and configurationally stable monofluoro acylboronates: effect of ligand structure on their formation, properties, and reactivities.

Journal of the American Chemical Society

Noda H, Bode JW.
PMID: 25723308
J Am Chem Soc. 2015 Mar 25;137(11):3958-66. doi: 10.1021/jacs.5b00822. Epub 2015 Mar 13.

The recent disclosures of two classes of acylborons, potassium acyltrifluoroborates (KATs) and N-methyliminodiacetyl (MIDA) acylboronates, demonstrated that certain acylboron species can be both remarkably stable and uniquely reactive. Here we report new classes of ligands for acylboronates that have...

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Noda H, Bode JW. Synthesis of chemically and configurationally stable monofluoro acylboronates: effect of ligand structure on their formation, properties, and reactivities. J Am Chem Soc. 2015;137(11):3958-66doi: 10.1021/jacs.5b00822.
Noda, H., & Bode, J. W. (2015). Synthesis of chemically and configurationally stable monofluoro acylboronates: effect of ligand structure on their formation, properties, and reactivities. Journal of the American Chemical Society, 137(11), 3958-66. https://doi.org/10.1021/jacs.5b00822
Noda, Hidetoshi, and Bode, Jeffrey W. "Synthesis of chemically and configurationally stable monofluoro acylboronates: effect of ligand structure on their formation, properties, and reactivities." Journal of the American Chemical Society vol. 137,11 (2015): 3958-66. doi: https://doi.org/10.1021/jacs.5b00822
Noda H, Bode JW. Synthesis of chemically and configurationally stable monofluoro acylboronates: effect of ligand structure on their formation, properties, and reactivities. J Am Chem Soc. 2015 Mar 25;137(11):3958-66. doi: 10.1021/jacs.5b00822. Epub 2015 Mar 13. PMID: 25723308.
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Importance of π-stacking interactions in the hydrogen atom transfer reactions from activated phenols to short-lived N-oxyl radicals.

The Journal of organic chemistry

Mazzonna M, Bietti M, DiLabio GA, Lanzalunga O, Salamone M.
PMID: 24784172
J Org Chem. 2014 Jun 06;79(11):5209-18. doi: 10.1021/jo500789v. Epub 2014 May 09.

A kinetic study of the hydrogen atom transfer from activated phenols (2,6-dimethyl- and 2,6-di-tert-butyl-4-substituted phenols, 2,2,5,7,8-pentamethylchroman-6-ol, caffeic acid, and (+)-cathechin) to a series of N-oxyl radical (4-substituted phthalimide-N-oxyl radicals (4-X-PINO), 6-substituted benzotriazole-N-oxyl radicals (6-Y-BTNO), 3-quinazolin-4-one-N-oxyl radical (QONO), and 3-benzotriazin-4-one-N-oxyl...

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Mazzonna M, Bietti M, DiLabio GA, et al. Importance of π-stacking interactions in the hydrogen atom transfer reactions from activated phenols to short-lived N-oxyl radicals. J Org Chem. 2014;79(11):5209-18doi: 10.1021/jo500789v.
Mazzonna, M., Bietti, M., DiLabio, G. A., Lanzalunga, O., & Salamone, M. (2014). Importance of π-stacking interactions in the hydrogen atom transfer reactions from activated phenols to short-lived N-oxyl radicals. The Journal of organic chemistry, 79(11), 5209-18. https://doi.org/10.1021/jo500789v
Mazzonna, Marco, et al. "Importance of π-stacking interactions in the hydrogen atom transfer reactions from activated phenols to short-lived N-oxyl radicals." The Journal of organic chemistry vol. 79,11 (2014): 5209-18. doi: https://doi.org/10.1021/jo500789v
Mazzonna M, Bietti M, DiLabio GA, Lanzalunga O, Salamone M. Importance of π-stacking interactions in the hydrogen atom transfer reactions from activated phenols to short-lived N-oxyl radicals. J Org Chem. 2014 Jun 06;79(11):5209-18. doi: 10.1021/jo500789v. Epub 2014 May 09. PMID: 24784172.
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Convenient preparation of O-linked polymer-bound N-substituted hydroxylamines, intermediates for synthesis of N-substituted hydroxamic acids.

Organic letters

Robinson DE, Holladay MW.
PMID: 10964363
Org Lett. 2000 Sep 07;2(18):2777-9. doi: 10.1021/ol006152g.

[reaction: see text] An efficient procedure for preparation of O-linked polymer-bound N-substituted hydroxylamines by reduction of resin-bound oximes with borane.pyridine complex in the presence of dichloroacetic acid is reported. Other reducing systems commonly used for imine or oxime reduction...

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Robinson DE, Holladay MW. Convenient preparation of O-linked polymer-bound N-substituted hydroxylamines, intermediates for synthesis of N-substituted hydroxamic acids. Org Lett. 2000;2(18):2777-9doi: 10.1021/ol006152g.
Robinson, D. E., & Holladay, M. W. (2000). Convenient preparation of O-linked polymer-bound N-substituted hydroxylamines, intermediates for synthesis of N-substituted hydroxamic acids. Organic letters, 2(18), 2777-9. https://doi.org/10.1021/ol006152g
Robinson, D E, and Holladay, M W. "Convenient preparation of O-linked polymer-bound N-substituted hydroxylamines, intermediates for synthesis of N-substituted hydroxamic acids." Organic letters vol. 2,18 (2000): 2777-9. doi: https://doi.org/10.1021/ol006152g
Robinson DE, Holladay MW. Convenient preparation of O-linked polymer-bound N-substituted hydroxylamines, intermediates for synthesis of N-substituted hydroxamic acids. Org Lett. 2000 Sep 07;2(18):2777-9. doi: 10.1021/ol006152g. PMID: 10964363.
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The kinetics and mechanism of the ferrate(VI) oxidation of hydroxylamines.

Inorganic chemistry

Johnson MD, Hornstein BJ.
PMID: 14552644
Inorg Chem. 2003 Oct 20;42(21):6923-8. doi: 10.1021/ic020705x.

Aqueous solutions of potassium ferrate(VI) cleanly and rapidly oxidize hydroxylamine to nitrous oxide, N-methylhydroxylamine to nitrosomethane, N-phenylhydroxylamine to nitrosobenzene, and O-methylhydroxylamine to methanol and nitrogen. The kinetics show first-order behavior with respect to each reactant and a two term...

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Johnson MD, Hornstein BJ. The kinetics and mechanism of the ferrate(VI) oxidation of hydroxylamines. Inorg Chem. 2003;42(21):6923-8doi: 10.1021/ic020705x.
Johnson, M. D., & Hornstein, B. J. (2003). The kinetics and mechanism of the ferrate(VI) oxidation of hydroxylamines. Inorganic chemistry, 42(21), 6923-8. https://doi.org/10.1021/ic020705x
Johnson, Michael D, and Hornstein, Brooks J. "The kinetics and mechanism of the ferrate(VI) oxidation of hydroxylamines." Inorganic chemistry vol. 42,21 (2003): 6923-8. doi: https://doi.org/10.1021/ic020705x
Johnson MD, Hornstein BJ. The kinetics and mechanism of the ferrate(VI) oxidation of hydroxylamines. Inorg Chem. 2003 Oct 20;42(21):6923-8. doi: 10.1021/ic020705x. PMID: 14552644.
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Nucleophilic attack by oxyanions on a phosphate monoester dianion: the positive effect of a cationic general Acid.

Journal of the American Chemical Society

Kirby AJ, Lima MF, da Silva D, Nome F.
PMID: 14759187
J Am Chem Soc. 2004 Feb 11;126(5):1350-1. doi: 10.1021/ja038428w.

The two negative charges on a phosphate monoester RO-PO32- at neutral pH provide a considerable electrostatic barrier toward reactions with nucleophilic reagents with a negative charge on the attacking atom. Electrostatic repulsion disappears when the hydrolysis of an aryl...

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Kirby AJ, Lima MF, da Silva D, et al. Nucleophilic attack by oxyanions on a phosphate monoester dianion: the positive effect of a cationic general Acid. J Am Chem Soc. 2004;126(5):1350-1doi: 10.1021/ja038428w.
Kirby, A. J., Lima, M. F., da Silva, D., & Nome, F. (2004). Nucleophilic attack by oxyanions on a phosphate monoester dianion: the positive effect of a cationic general Acid. Journal of the American Chemical Society, 126(5), 1350-1. https://doi.org/10.1021/ja038428w
Kirby, Anthony J, et al. "Nucleophilic attack by oxyanions on a phosphate monoester dianion: the positive effect of a cationic general Acid." Journal of the American Chemical Society vol. 126,5 (2004): 1350-1. doi: https://doi.org/10.1021/ja038428w
Kirby AJ, Lima MF, da Silva D, Nome F. Nucleophilic attack by oxyanions on a phosphate monoester dianion: the positive effect of a cationic general Acid. J Am Chem Soc. 2004 Feb 11;126(5):1350-1. doi: 10.1021/ja038428w. PMID: 14759187.
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O-Protected 3-hydroxy-oxazolidin-2,4-diones: novel precursors in the synthesis of alpha-hydroxyhydroxamic acids.

Organic & biomolecular chemistry

Kurz T, Widyan K.
PMID: 15254629
Org Biomol Chem. 2004 Jul 21;2(14):2023-7. doi: 10.1039/b404950k. Epub 2004 Jun 21.

O-Protected 3-hydroxyoxazolidin-2,4-diones have been prepared in a novel one-pot reaction by subsequent treatment of cyanohydrins with 1,1'-carbonyldiimidazole and O-protected hydroxylamines followed by acidic hydrolysis of the intermediate 4-imino-oxazolidin-2-ones. Decarbonylation of O-protected 3-hydroxyoxazolidin-2,4-diones by catalytic amounts of sodium methoxide, lithium...

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Kurz T, Widyan K. O-Protected 3-hydroxy-oxazolidin-2,4-diones: novel precursors in the synthesis of alpha-hydroxyhydroxamic acids. Org Biomol Chem. 2004;2(14):2023-7doi: 10.1039/b404950k.
Kurz, T., & Widyan, K. (2004). O-Protected 3-hydroxy-oxazolidin-2,4-diones: novel precursors in the synthesis of alpha-hydroxyhydroxamic acids. Organic & biomolecular chemistry, 2(14), 2023-7. https://doi.org/10.1039/b404950k
Kurz, Thomas, and Widyan, Khalid. "O-Protected 3-hydroxy-oxazolidin-2,4-diones: novel precursors in the synthesis of alpha-hydroxyhydroxamic acids." Organic & biomolecular chemistry vol. 2,14 (2004): 2023-7. doi: https://doi.org/10.1039/b404950k
Kurz T, Widyan K. O-Protected 3-hydroxy-oxazolidin-2,4-diones: novel precursors in the synthesis of alpha-hydroxyhydroxamic acids. Org Biomol Chem. 2004 Jul 21;2(14):2023-7. doi: 10.1039/b404950k. Epub 2004 Jun 21. PMID: 15254629.
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Enantioselective addition of vinylzinc reagents to 3,4-dihydroisoquinoline N-oxide.

Organic letters

Wang S, Seto CT.
PMID: 16928053
Org Lett. 2006 Aug 31;8(18):3979-82. doi: 10.1021/ol0614525.

Ligand 2a promotes the enantioselective addition of vinylzinc reagents to 3,4-dihydroisoquinoline N-oxide to yield chiral allylic hydroxylamines. With 0.1 equiv of the ligand, the product is obtained in up to 84% ee, whereas with 1.2 equiv of the ligand,...

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Wang S, Seto CT. Enantioselective addition of vinylzinc reagents to 3,4-dihydroisoquinoline N-oxide. Org Lett. 2006;8(18):3979-82doi: 10.1021/ol0614525.
Wang, S., & Seto, C. T. (2006). Enantioselective addition of vinylzinc reagents to 3,4-dihydroisoquinoline N-oxide. Organic letters, 8(18), 3979-82. https://doi.org/10.1021/ol0614525
Wang, Sa, and Seto, Christopher T. "Enantioselective addition of vinylzinc reagents to 3,4-dihydroisoquinoline N-oxide." Organic letters vol. 8,18 (2006): 3979-82. doi: https://doi.org/10.1021/ol0614525
Wang S, Seto CT. Enantioselective addition of vinylzinc reagents to 3,4-dihydroisoquinoline N-oxide. Org Lett. 2006 Aug 31;8(18):3979-82. doi: 10.1021/ol0614525. PMID: 16928053.
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Showing 1 to 12 of 176 entries