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Photocatalytic Radical Trifluoromethylation/Cyclization Cascade: Synthesis of CF3-Containing Pyrazolines and Isoxazolines.

Organic letters

Wei Q, Chen JR, Hu XQ, Yang XC, Lu B, Xiao WJ.
PMID: 26332823
Org Lett. 2015 Sep 18;17(18):4464-7. doi: 10.1021/acs.orglett.5b02118. Epub 2015 Sep 02.

A general visible light induced photoredox-catalyzed radical trifluoromethylation/cyclization cascade of β-aryl-β,γ-unsaturated hydrazones and oximes is described. The protocol enables an efficient access to various densely functionalized and biologically important CF3-containing dihydropyrazoles and isoxazolines with generally high yields.

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Wei Q, Chen JR, Hu XQ, et al. Photocatalytic Radical Trifluoromethylation/Cyclization Cascade: Synthesis of CF3-Containing Pyrazolines and Isoxazolines. Org Lett. 2015;17(18):4464-7doi: 10.1021/acs.orglett.5b02118.
Wei, Q., Chen, J. R., Hu, X. Q., Yang, X. C., Lu, B., & Xiao, W. J. (2015). Photocatalytic Radical Trifluoromethylation/Cyclization Cascade: Synthesis of CF3-Containing Pyrazolines and Isoxazolines. Organic letters, 17(18), 4464-7. https://doi.org/10.1021/acs.orglett.5b02118
Wei, Qiang, et al. "Photocatalytic Radical Trifluoromethylation/Cyclization Cascade: Synthesis of CF3-Containing Pyrazolines and Isoxazolines." Organic letters vol. 17,18 (2015): 4464-7. doi: https://doi.org/10.1021/acs.orglett.5b02118
Wei Q, Chen JR, Hu XQ, Yang XC, Lu B, Xiao WJ. Photocatalytic Radical Trifluoromethylation/Cyclization Cascade: Synthesis of CF3-Containing Pyrazolines and Isoxazolines. Org Lett. 2015 Sep 18;17(18):4464-7. doi: 10.1021/acs.orglett.5b02118. Epub 2015 Sep 02. PMID: 26332823.
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On the roles of close shell interactions in the structure of acyl-substituted hydrazones: An experimental and theoretical approach.

Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy

Saeed A, Ifzan Arshad M, Bolte M, Fantoni AC, Delgado Espinoza ZY, Erben MF.
PMID: 26761413
Spectrochim Acta A Mol Biomol Spectrosc. 2016 Mar 15;157:138-145. doi: 10.1016/j.saa.2015.12.026. Epub 2015 Dec 24.

The 2-(phenyl-hydrazono)-succinic acid dimethyl ester compound was synthesized by reacting phenylhydrazine with dimethylacetylene dicarboxylate at room temperature and characterized by elemental analysis, infrared, Raman, (1)H and (13)C NMR spectroscopies and mass spectrometry. Its solid state structure was determined by...

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Saeed A, Ifzan Arshad M, Bolte M, et al. On the roles of close shell interactions in the structure of acyl-substituted hydrazones: An experimental and theoretical approach. Spectrochim Acta A Mol Biomol Spectrosc. 2015;157:138-145doi: 10.1016/j.saa.2015.12.026.
Saeed, A., Ifzan Arshad, M., Bolte, M., Fantoni, A. C., Delgado Espinoza, Z. Y., & Erben, M. F. (2016). On the roles of close shell interactions in the structure of acyl-substituted hydrazones: An experimental and theoretical approach. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 157138-145. https://doi.org/10.1016/j.saa.2015.12.026
Saeed, Aamer, et al. "On the roles of close shell interactions in the structure of acyl-substituted hydrazones: An experimental and theoretical approach." Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy vol. 157 (2016): 138-145. doi: https://doi.org/10.1016/j.saa.2015.12.026
Saeed A, Ifzan Arshad M, Bolte M, Fantoni AC, Delgado Espinoza ZY, Erben MF. On the roles of close shell interactions in the structure of acyl-substituted hydrazones: An experimental and theoretical approach. Spectrochim Acta A Mol Biomol Spectrosc. 2016 Mar 15;157:138-145. doi: 10.1016/j.saa.2015.12.026. Epub 2015 Dec 24. PMID: 26761413.
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1,3-Dipolar cycloadditions of azomethine imines.

Organic & biomolecular chemistry

Nájera C, Sansano JM, Yus M.
PMID: 26140443
Org Biomol Chem. 2015 Aug 28;13(32):8596-636. doi: 10.1039/c5ob01086a. Epub 2015 Jul 03.

Azomethine imines are considered 1,3-dipoles of the aza-allyl type which are transient intermediates and should be generated in situ but can also be stable and isolable compounds. They react with electron-rich and electron-poor olefins as well as with acetylenic...

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Nájera C, Sansano JM, Yus M. 1,3-Dipolar cycloadditions of azomethine imines. Org Biomol Chem. 2015;13(32):8596-636doi: 10.1039/c5ob01086a.
Nájera, C., Sansano, J. M., & Yus, M. (2015). 1,3-Dipolar cycloadditions of azomethine imines. Organic & biomolecular chemistry, 13(32), 8596-636. https://doi.org/10.1039/c5ob01086a
Nájera, Carmen, et al. "1,3-Dipolar cycloadditions of azomethine imines." Organic & biomolecular chemistry vol. 13,32 (2015): 8596-636. doi: https://doi.org/10.1039/c5ob01086a
Nájera C, Sansano JM, Yus M. 1,3-Dipolar cycloadditions of azomethine imines. Org Biomol Chem. 2015 Aug 28;13(32):8596-636. doi: 10.1039/c5ob01086a. Epub 2015 Jul 03. PMID: 26140443.
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A three-membered ring approach to carbonyl olefination.

Nature communications

Niyomchon S, Oppedisano A, Aillard P, Maulide N.
PMID: 29061994
Nat Commun. 2017 Oct 23;8(1):1091. doi: 10.1038/s41467-017-01036-y.

The carbon-carbon double bond, with its diverse and multifaceted reactivity, occupies a prominent position in organic synthesis. Although a variety of simple alkenes are readily available, the mild and chemoselective introduction of a unit of unsaturation into a functionalized...

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Niyomchon S, Oppedisano A, Aillard P, et al. A three-membered ring approach to carbonyl olefination. Nat Commun. 2017;8(1):1091doi: 10.1038/s41467-017-01036-y.
Niyomchon, S., Oppedisano, A., Aillard, P., & Maulide, N. (2017). A three-membered ring approach to carbonyl olefination. Nature communications, 8(1), 1091. https://doi.org/10.1038/s41467-017-01036-y
Niyomchon, Supaporn, et al. "A three-membered ring approach to carbonyl olefination." Nature communications vol. 8,1 (2017): 1091. doi: https://doi.org/10.1038/s41467-017-01036-y
Niyomchon S, Oppedisano A, Aillard P, Maulide N. A three-membered ring approach to carbonyl olefination. Nat Commun. 2017 Oct 23;8(1):1091. doi: 10.1038/s41467-017-01036-y. PMID: 29061994; PMCID: PMC5653658.
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A Novel Anti-Hepatitis C Virus and Antiproliferative Agent Alters Metabolic Networks in HepG2 and Hep3B Cells.

Metabolites

Keogh A, Şenkardeş S, Idle JR, Küçükgüzel ŞG, Beyoğlu D.
PMID: 28574427
Metabolites. 2017 Jun 02;7(2). doi: 10.3390/metabo7020023.

A series of novel diflunisal hydrazide-hydrazones has been reported together with their anti-hepatitis C virus and antiproliferative activities in a number of human hepatoma cell lines. However, the mechanisms underlying the efficacy of these agents remain unclear. It was...

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Keogh A, Şenkardeş S, Idle JR, et al. A Novel Anti-Hepatitis C Virus and Antiproliferative Agent Alters Metabolic Networks in HepG2 and Hep3B Cells. Metabolites. 2017;7(2)doi: 10.3390/metabo7020023.
Keogh, A., Şenkardeş, S., Idle, J. R., Küçükgüzel, �. �. G., & Beyoğlu, D. (2017). A Novel Anti-Hepatitis C Virus and Antiproliferative Agent Alters Metabolic Networks in HepG2 and Hep3B Cells. Metabolites, 7(2), . https://doi.org/10.3390/metabo7020023
Keogh, Adrian, et al. "A Novel Anti-Hepatitis C Virus and Antiproliferative Agent Alters Metabolic Networks in HepG2 and Hep3B Cells." Metabolites vol. 7,2 (2017). doi: https://doi.org/10.3390/metabo7020023
Keogh A, Şenkardeş S, Idle JR, Küçükgüzel ŞG, Beyoğlu D. A Novel Anti-Hepatitis C Virus and Antiproliferative Agent Alters Metabolic Networks in HepG2 and Hep3B Cells. Metabolites. 2017 Jun 02;7(2). doi: 10.3390/metabo7020023. PMID: 28574427; PMCID: PMC5487994.
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Visible-Light Photoredox-Catalyzed C-H Difluoroalkylation of Hydrazones through an Aminyl Radical/Polar Mechanism.

Angewandte Chemie (International ed. in English)

Xu P, Wang G, Zhu Y, Li W, Cheng Y, Li S, Zhu C.
PMID: 26592803
Angew Chem Int Ed Engl. 2016 Feb 18;55(8):2939-43. doi: 10.1002/anie.201508698. Epub 2015 Nov 23.

An unprecedented visible-light-induced direct C-H bond difluoroalkylation of aldehyde-derived hydrazones was developed. This reaction represents a new way to synthesize substituted hydrazones. The salient features of this reaction include difluorinated hydrazone synthesis rather than classical amine synthesis, extremely mild...

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Xu P, Wang G, Zhu Y, et al. Visible-Light Photoredox-Catalyzed C-H Difluoroalkylation of Hydrazones through an Aminyl Radical/Polar Mechanism. Angew Chem Int Ed Engl. 2015;55(8):2939-43doi: 10.1002/anie.201508698.
Xu, P., Wang, G., Zhu, Y., Li, W., Cheng, Y., Li, S., & Zhu, C. (2016). Visible-Light Photoredox-Catalyzed C-H Difluoroalkylation of Hydrazones through an Aminyl Radical/Polar Mechanism. Angewandte Chemie (International ed. in English), 55(8), 2939-43. https://doi.org/10.1002/anie.201508698
Xu, Pan, et al. "Visible-Light Photoredox-Catalyzed C-H Difluoroalkylation of Hydrazones through an Aminyl Radical/Polar Mechanism." Angewandte Chemie (International ed. in English) vol. 55,8 (2016): 2939-43. doi: https://doi.org/10.1002/anie.201508698
Xu P, Wang G, Zhu Y, Li W, Cheng Y, Li S, Zhu C. Visible-Light Photoredox-Catalyzed C-H Difluoroalkylation of Hydrazones through an Aminyl Radical/Polar Mechanism. Angew Chem Int Ed Engl. 2016 Feb 18;55(8):2939-43. doi: 10.1002/anie.201508698. Epub 2015 Nov 23. PMID: 26592803.
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HOF·CH3CN: probably the best oxygen transfer agent organic chemistry has to offer.

Accounts of chemical research

Rozen S.
PMID: 24871453
Acc Chem Res. 2014 Aug 19;47(8):2378-89. doi: 10.1021/ar500107b. Epub 2014 May 28.

The complex HOF·CH3CN is readily obtained by bubbling dilute fluorine into aqueous acetonitrile solution. It does not have to be purified or isolated, and its solution can react as is, after the concentration has been establish by any iodometric...

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Rozen S. HOF·CH3CN: probably the best oxygen transfer agent organic chemistry has to offer. Acc Chem Res. 2014;47(8):2378-89doi: 10.1021/ar500107b.
Rozen, S. (2014). HOF·CH3CN: probably the best oxygen transfer agent organic chemistry has to offer. Accounts of chemical research, 47(8), 2378-89. https://doi.org/10.1021/ar500107b
Rozen, Shlomo. "HOF·CH3CN: probably the best oxygen transfer agent organic chemistry has to offer." Accounts of chemical research vol. 47,8 (2014): 2378-89. doi: https://doi.org/10.1021/ar500107b
Rozen S. HOF·CH3CN: probably the best oxygen transfer agent organic chemistry has to offer. Acc Chem Res. 2014 Aug 19;47(8):2378-89. doi: 10.1021/ar500107b. Epub 2014 May 28. PMID: 24871453.
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Hydrazonyl Radical-Participated Tandem Reaction: A Strategy for the Synthesis of Pyrazoline-Functionalized Oxindoles.

Organic letters

Duan XY, Yang XL, Jia PP, Zhang M, Han B.
PMID: 26641278
Org Lett. 2015 Dec 18;17(24):6022-5. doi: 10.1021/acs.orglett.5b03003. Epub 2015 Dec 07.

An efficient and practical tandem cyclization/addition/cyclization strategy is developed for the initial generated hydrazonyl radicals derived from the oxidation of β,γ-unsaturated hydrazones. By using this protocol, structurally novel pyrazoline-functionalized oxindoles are prepared by the reaction of easily accessible β,γ-unsaturated...

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Duan XY, Yang XL, Jia PP, et al. Hydrazonyl Radical-Participated Tandem Reaction: A Strategy for the Synthesis of Pyrazoline-Functionalized Oxindoles. Org Lett. 2015;17(24):6022-5doi: 10.1021/acs.orglett.5b03003.
Duan, X. Y., Yang, X. L., Jia, P. P., Zhang, M., & Han, B. (2015). Hydrazonyl Radical-Participated Tandem Reaction: A Strategy for the Synthesis of Pyrazoline-Functionalized Oxindoles. Organic letters, 17(24), 6022-5. https://doi.org/10.1021/acs.orglett.5b03003
Duan, Xiao-Yong, et al. "Hydrazonyl Radical-Participated Tandem Reaction: A Strategy for the Synthesis of Pyrazoline-Functionalized Oxindoles." Organic letters vol. 17,24 (2015): 6022-5. doi: https://doi.org/10.1021/acs.orglett.5b03003
Duan XY, Yang XL, Jia PP, Zhang M, Han B. Hydrazonyl Radical-Participated Tandem Reaction: A Strategy for the Synthesis of Pyrazoline-Functionalized Oxindoles. Org Lett. 2015 Dec 18;17(24):6022-5. doi: 10.1021/acs.orglett.5b03003. Epub 2015 Dec 07. PMID: 26641278.
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Diazirines as potent electrophilic nitrogen sources: application to the synthesis of pyrazoles.

Organic letters

Schneider Y, Prévost J, Gobin M, Legault CY.
PMID: 24378081
Org Lett. 2014 Jan 17;16(2):596-9. doi: 10.1021/ol403495e. Epub 2013 Dec 30.

Even after more than 50 years since its discovery, the electrophilic potential of diazirines was never truly exploited. This longstanding limitation has been resolved. N-Monosubstituted diaziridines and hydrazones are obtained by nucleophilic additions. They release, under hydrolysis conditions, the...

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Schneider Y, Prévost J, Gobin M, et al. Diazirines as potent electrophilic nitrogen sources: application to the synthesis of pyrazoles. Org Lett. 2013;16(2):596-9doi: 10.1021/ol403495e.
Schneider, Y., Prévost, J., Gobin, M., & Legault, C. Y. (2014). Diazirines as potent electrophilic nitrogen sources: application to the synthesis of pyrazoles. Organic letters, 16(2), 596-9. https://doi.org/10.1021/ol403495e
Schneider, Yoann, et al. "Diazirines as potent electrophilic nitrogen sources: application to the synthesis of pyrazoles." Organic letters vol. 16,2 (2014): 596-9. doi: https://doi.org/10.1021/ol403495e
Schneider Y, Prévost J, Gobin M, Legault CY. Diazirines as potent electrophilic nitrogen sources: application to the synthesis of pyrazoles. Org Lett. 2014 Jan 17;16(2):596-9. doi: 10.1021/ol403495e. Epub 2013 Dec 30. PMID: 24378081.
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Multicomponent Coupling Reactions of Two N-Tosyl Hydrazones and Elemental Sulfur: Selective Denitrogenation Pathway toward Unsymmetric 2,5-Disubstituted 1,3,4-Thiadiazoles.

Organic letters

Zhou Z, Liu Y, Chen J, Yao E, Cheng J.
PMID: 27684432
Org Lett. 2016 Oct 21;18(20):5268-5271. doi: 10.1021/acs.orglett.6b02583. Epub 2016 Sep 29.

A copper-mediated, three-component reaction between two different N-Ts hydrazones and elemental sulfur was developed, leading to a series of unsymmetric 2,5-disubstituted 1,3,4-thiadiazoles in moderate yields with good functional group compatibility. This procedure features the employment of elemental sulfur and...

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Zhou Z, Liu Y, Chen J, et al. Multicomponent Coupling Reactions of Two N-Tosyl Hydrazones and Elemental Sulfur: Selective Denitrogenation Pathway toward Unsymmetric 2,5-Disubstituted 1,3,4-Thiadiazoles. Org Lett. 2016;18(20):5268-5271doi: 10.1021/acs.orglett.6b02583.
Zhou, Z., Liu, Y., Chen, J., Yao, E., & Cheng, J. (2016). Multicomponent Coupling Reactions of Two N-Tosyl Hydrazones and Elemental Sulfur: Selective Denitrogenation Pathway toward Unsymmetric 2,5-Disubstituted 1,3,4-Thiadiazoles. Organic letters, 18(20), 5268-5271. https://doi.org/10.1021/acs.orglett.6b02583
Zhou, Zhen, et al. "Multicomponent Coupling Reactions of Two N-Tosyl Hydrazones and Elemental Sulfur: Selective Denitrogenation Pathway toward Unsymmetric 2,5-Disubstituted 1,3,4-Thiadiazoles." Organic letters vol. 18,20 (2016): 5268-5271. doi: https://doi.org/10.1021/acs.orglett.6b02583
Zhou Z, Liu Y, Chen J, Yao E, Cheng J. Multicomponent Coupling Reactions of Two N-Tosyl Hydrazones and Elemental Sulfur: Selective Denitrogenation Pathway toward Unsymmetric 2,5-Disubstituted 1,3,4-Thiadiazoles. Org Lett. 2016 Oct 21;18(20):5268-5271. doi: 10.1021/acs.orglett.6b02583. Epub 2016 Sep 29. PMID: 27684432.
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Aqueous Sulfate Separation by Crystallization of Sulfate-Water Clusters.

Angewandte Chemie (International ed. in English)

Custelcean R, Williams NJ, Seipp CA.
PMID: 26252802
Angew Chem Int Ed Engl. 2015 Sep 01;54(36):10525-9. doi: 10.1002/anie.201506314. Epub 2015 Aug 07.

An effective approach to sulfate separation from aqueous solutions is based on the crystallization of extended [SO4(H2O)5(2-)]n sulfate-water clusters with a bis(guanidinium) ligand. The ligand was generated in situ by hydrazone condensation in water, thereby bypassing the need for...

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Custelcean R, Williams NJ, Seipp CA. Aqueous Sulfate Separation by Crystallization of Sulfate-Water Clusters. Angew Chem Int Ed Engl. 2015;54(36):10525-9doi: 10.1002/anie.201506314.
Custelcean, R., Williams, N. J., & Seipp, C. A. (2015). Aqueous Sulfate Separation by Crystallization of Sulfate-Water Clusters. Angewandte Chemie (International ed. in English), 54(36), 10525-9. https://doi.org/10.1002/anie.201506314
Custelcean, Radu, et al. "Aqueous Sulfate Separation by Crystallization of Sulfate-Water Clusters." Angewandte Chemie (International ed. in English) vol. 54,36 (2015): 10525-9. doi: https://doi.org/10.1002/anie.201506314
Custelcean R, Williams NJ, Seipp CA. Aqueous Sulfate Separation by Crystallization of Sulfate-Water Clusters. Angew Chem Int Ed Engl. 2015 Sep 01;54(36):10525-9. doi: 10.1002/anie.201506314. Epub 2015 Aug 07. PMID: 26252802.
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Base-Promoted/Gold-Catalyzed Intramolecular Highly Selective and Controllable Detosylative Cyclization.

Chemistry (Weinheim an der Bergstrasse, Germany)

Zhu C, Qiu L, Xu G, Li J, Sun J.
PMID: 26223908
Chemistry. 2015 Sep 07;21(37):12871-5. doi: 10.1002/chem.201502073. Epub 2015 Jul 29.

A highly selective, controllable and synthetically useful base-promoted intramolecular detosylative cyclization of bis-N-tosylhydrazones has been achieved, affording N-containing heterocycles and cyclic olefins under transition-metal-free or gold-catalyzed procedures, respectively. Moreover, an effective and practical metal-free or gold-catalyzed approach to synthesize...

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Zhu C, Qiu L, Xu G, et al. Base-Promoted/Gold-Catalyzed Intramolecular Highly Selective and Controllable Detosylative Cyclization. Chemistry. 2015;21(37):12871-5doi: 10.1002/chem.201502073.
Zhu, C., Qiu, L., Xu, G., Li, J., & Sun, J. (2015). Base-Promoted/Gold-Catalyzed Intramolecular Highly Selective and Controllable Detosylative Cyclization. Chemistry (Weinheim an der Bergstrasse, Germany), 21(37), 12871-5. https://doi.org/10.1002/chem.201502073
Zhu, Chenghao, et al. "Base-Promoted/Gold-Catalyzed Intramolecular Highly Selective and Controllable Detosylative Cyclization." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,37 (2015): 12871-5. doi: https://doi.org/10.1002/chem.201502073
Zhu C, Qiu L, Xu G, Li J, Sun J. Base-Promoted/Gold-Catalyzed Intramolecular Highly Selective and Controllable Detosylative Cyclization. Chemistry. 2015 Sep 07;21(37):12871-5. doi: 10.1002/chem.201502073. Epub 2015 Jul 29. PMID: 26223908.
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Showing 1 to 12 of 533 entries