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Amine Directed Pd(II)-Catalyzed C-H Activation-Intramolecular Amination of N-Het(aryl)/Acyl Enaminonitriles and Enaminones: An Approach towards Multisubstituted Indoles and Heterofused Pyrroles.

The Journal of organic chemistry

Yugandar S, Konda S, Ila H.
PMID: 26842134
J Org Chem. 2016 Mar 04;81(5):2035-52. doi: 10.1021/acs.joc.5b02902. Epub 2016 Feb 18.

An efficient route to multisubstituted indoles has been developed through intramolecular oxidative C-H activation-amination of readily available 2-(het)aryl-3-(het)aryl/alkyl-3-(het)aryl/acylaminoacrylonitrile/enaminone precursors in the presence of either palladium acetate/cupric acetate catalytic system under oxygen atmosphere or palladium acetate/silver carbonate in the presence...

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Yugandar S, Konda S, Ila H. Amine Directed Pd(II)-Catalyzed C-H Activation-Intramolecular Amination of N-Het(aryl)/Acyl Enaminonitriles and Enaminones: An Approach towards Multisubstituted Indoles and Heterofused Pyrroles. J Org Chem. 2016;81(5):2035-52doi: 10.1021/acs.joc.5b02902.
Yugandar, S., Konda, S., & Ila, H. (2016). Amine Directed Pd(II)-Catalyzed C-H Activation-Intramolecular Amination of N-Het(aryl)/Acyl Enaminonitriles and Enaminones: An Approach towards Multisubstituted Indoles and Heterofused Pyrroles. The Journal of organic chemistry, 81(5), 2035-52. https://doi.org/10.1021/acs.joc.5b02902
Yugandar, Somaraju, et al. "Amine Directed Pd(II)-Catalyzed C-H Activation-Intramolecular Amination of N-Het(aryl)/Acyl Enaminonitriles and Enaminones: An Approach towards Multisubstituted Indoles and Heterofused Pyrroles." The Journal of organic chemistry vol. 81,5 (2016): 2035-52. doi: https://doi.org/10.1021/acs.joc.5b02902
Yugandar S, Konda S, Ila H. Amine Directed Pd(II)-Catalyzed C-H Activation-Intramolecular Amination of N-Het(aryl)/Acyl Enaminonitriles and Enaminones: An Approach towards Multisubstituted Indoles and Heterofused Pyrroles. J Org Chem. 2016 Mar 04;81(5):2035-52. doi: 10.1021/acs.joc.5b02902. Epub 2016 Feb 18. PMID: 26842134.
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From unsuccessful H2-activation with FLPs containing B(Ohfip)3 to a systematic evaluation of the Lewis acidity of 33 Lewis acids based on fluoride, chloride, hydride and methyl ion affinities.

Dalton transactions (Cambridge, England : 2003)

Böhrer H, Trapp N, Himmel D, Schleep M, Krossing I.
PMID: 25803574
Dalton Trans. 2015 Apr 28;44(16):7489-99. doi: 10.1039/c4dt02822h.

The possibility of obtaining frustrated Lewis pairs (FLPs) suitable for H2-activation based on the Lewis acid B(Ohfip)3 1 (Ohfip = OC(H)(CF3)2) was investigated. In this context, the crystal structure of 1 as well as the crystal structure of the...

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Böhrer H, Trapp N, Himmel D, et al. From unsuccessful H2-activation with FLPs containing B(Ohfip)3 to a systematic evaluation of the Lewis acidity of 33 Lewis acids based on fluoride, chloride, hydride and methyl ion affinities. Dalton Trans. 2015;44(16):7489-99doi: 10.1039/c4dt02822h.
Böhrer, H., Trapp, N., Himmel, D., Schleep, M., & Krossing, I. (2015). From unsuccessful H2-activation with FLPs containing B(Ohfip)3 to a systematic evaluation of the Lewis acidity of 33 Lewis acids based on fluoride, chloride, hydride and methyl ion affinities. Dalton transactions (Cambridge, England : 2003), 44(16), 7489-99. https://doi.org/10.1039/c4dt02822h
Böhrer, Hannes, et al. "From unsuccessful H2-activation with FLPs containing B(Ohfip)3 to a systematic evaluation of the Lewis acidity of 33 Lewis acids based on fluoride, chloride, hydride and methyl ion affinities." Dalton transactions (Cambridge, England : 2003) vol. 44,16 (2015): 7489-99. doi: https://doi.org/10.1039/c4dt02822h
Böhrer H, Trapp N, Himmel D, Schleep M, Krossing I. From unsuccessful H2-activation with FLPs containing B(Ohfip)3 to a systematic evaluation of the Lewis acidity of 33 Lewis acids based on fluoride, chloride, hydride and methyl ion affinities. Dalton Trans. 2015 Apr 28;44(16):7489-99. doi: 10.1039/c4dt02822h. PMID: 25803574.
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Pyrrolo[2,3-c]pyridines as Imaging Agents for Neurofibrilary Tangles.

ACS medicinal chemistry letters

Blass B.
PMID: 27190589
ACS Med Chem Lett. 2016 Mar 14;7(5):444-6. doi: 10.1021/acsmedchemlett.6b00078. eCollection 2016 May 12.

No abstract available.

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Blass B. Pyrrolo[2,3-c]pyridines as Imaging Agents for Neurofibrilary Tangles. ACS Med Chem Lett. 2016;7(5):444-6doi: 10.1021/acsmedchemlett.6b00078.
Blass, B. (2016). Pyrrolo[2,3-c]pyridines as Imaging Agents for Neurofibrilary Tangles. ACS medicinal chemistry letters, 7(5), 444-6. https://doi.org/10.1021/acsmedchemlett.6b00078
Blass, Benjamin. "Pyrrolo[2,3-c]pyridines as Imaging Agents for Neurofibrilary Tangles." ACS medicinal chemistry letters vol. 7,5 (2016): 444-6. doi: https://doi.org/10.1021/acsmedchemlett.6b00078
Blass B. Pyrrolo[2,3-c]pyridines as Imaging Agents for Neurofibrilary Tangles. ACS Med Chem Lett. 2016 Mar 14;7(5):444-6. doi: 10.1021/acsmedchemlett.6b00078. eCollection 2016 May 12. PMID: 27190589; PMCID: PMC4867488.
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Trivalent Zirconium and Hafnium Metal-Organic Frameworks for Catalytic 1,4-Dearomative Additions of Pyridines and Quinolines.

Journal of the American Chemical Society

Ji P, Feng X, Veroneau SS, Song Y, Lin W.
PMID: 29041776
J Am Chem Soc. 2017 Nov 08;139(44):15600-15603. doi: 10.1021/jacs.7b09093. Epub 2017 Oct 25.

We report the quantitative conversion of [M

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Ji P, Feng X, Veroneau SS, et al. Trivalent Zirconium and Hafnium Metal-Organic Frameworks for Catalytic 1,4-Dearomative Additions of Pyridines and Quinolines. J Am Chem Soc. 2017;139(44):15600-15603doi: 10.1021/jacs.7b09093.
Ji, P., Feng, X., Veroneau, S. S., Song, Y., & Lin, W. (2017). Trivalent Zirconium and Hafnium Metal-Organic Frameworks for Catalytic 1,4-Dearomative Additions of Pyridines and Quinolines. Journal of the American Chemical Society, 139(44), 15600-15603. https://doi.org/10.1021/jacs.7b09093
Ji, Pengfei, et al. "Trivalent Zirconium and Hafnium Metal-Organic Frameworks for Catalytic 1,4-Dearomative Additions of Pyridines and Quinolines." Journal of the American Chemical Society vol. 139,44 (2017): 15600-15603. doi: https://doi.org/10.1021/jacs.7b09093
Ji P, Feng X, Veroneau SS, Song Y, Lin W. Trivalent Zirconium and Hafnium Metal-Organic Frameworks for Catalytic 1,4-Dearomative Additions of Pyridines and Quinolines. J Am Chem Soc. 2017 Nov 08;139(44):15600-15603. doi: 10.1021/jacs.7b09093. Epub 2017 Oct 25. PMID: 29041776.
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Rhodium-Catalyzed Atroposelective [2 + 2 + 2] Cycloaddition of Ortho-Substituted Phenyl Diynes with Nitriles: Effect of Ortho Substituents on Regio- and Enantioselectivity.

Organic letters

Kashima K, Teraoka K, Uekusa H, Shibata Y, Tanaka K.
PMID: 27074498
Org Lett. 2016 May 06;18(9):2170-3. doi: 10.1021/acs.orglett.6b00791. Epub 2016 Apr 13.

Axially chiral 3-(2-halophenyl)pyridines were successfully synthesized in high yields with excellent enantioselectivity by the cationic rhodium(I)/(S)-H8-BINAP complex-catalyzed atroposelective [2 + 2 + 2] cycloaddition of (o-halophenyl)diynes with nitriles. Interestingly, regio- and enantioselectivity highly depend on ortho substituents on the...

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Kashima K, Teraoka K, Uekusa H, et al. Rhodium-Catalyzed Atroposelective [2 + 2 + 2] Cycloaddition of Ortho-Substituted Phenyl Diynes with Nitriles: Effect of Ortho Substituents on Regio- and Enantioselectivity. Org Lett. 2016;18(9):2170-3doi: 10.1021/acs.orglett.6b00791.
Kashima, K., Teraoka, K., Uekusa, H., Shibata, Y., & Tanaka, K. (2016). Rhodium-Catalyzed Atroposelective [2 + 2 + 2] Cycloaddition of Ortho-Substituted Phenyl Diynes with Nitriles: Effect of Ortho Substituents on Regio- and Enantioselectivity. Organic letters, 18(9), 2170-3. https://doi.org/10.1021/acs.orglett.6b00791
Kashima, Kenichi, et al. "Rhodium-Catalyzed Atroposelective [2 + 2 + 2] Cycloaddition of Ortho-Substituted Phenyl Diynes with Nitriles: Effect of Ortho Substituents on Regio- and Enantioselectivity." Organic letters vol. 18,9 (2016): 2170-3. doi: https://doi.org/10.1021/acs.orglett.6b00791
Kashima K, Teraoka K, Uekusa H, Shibata Y, Tanaka K. Rhodium-Catalyzed Atroposelective [2 + 2 + 2] Cycloaddition of Ortho-Substituted Phenyl Diynes with Nitriles: Effect of Ortho Substituents on Regio- and Enantioselectivity. Org Lett. 2016 May 06;18(9):2170-3. doi: 10.1021/acs.orglett.6b00791. Epub 2016 Apr 13. PMID: 27074498.
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Structures, Lewis Acidities, Electrophilicities, and Protecting Group Abilities of Phenylfluorenylium and Tritylium Ions.

Chemistry (Weinheim an der Bergstrasse, Germany)

Follet E, Mayer P, Berionni G.
PMID: 27723164
Chemistry. 2017 Jan 12;23(3):623-630. doi: 10.1002/chem.201603963. Epub 2016 Dec 05.

The isolation, characterization, and the first X-ray structures of a fluorenylium ion and its Lewis adducts with nitrogen- and phosphorus-centered Lewis bases are reported. Kinetics of the reactions of a series of fluorenylium ions with reference π-, σ-, and...

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Follet E, Mayer P, Berionni G. Structures, Lewis Acidities, Electrophilicities, and Protecting Group Abilities of Phenylfluorenylium and Tritylium Ions. Chemistry. 2016;23(3):623-630doi: 10.1002/chem.201603963.
Follet, E., Mayer, P., & Berionni, G. (2017). Structures, Lewis Acidities, Electrophilicities, and Protecting Group Abilities of Phenylfluorenylium and Tritylium Ions. Chemistry (Weinheim an der Bergstrasse, Germany), 23(3), 623-630. https://doi.org/10.1002/chem.201603963
Follet, Elsa, et al. "Structures, Lewis Acidities, Electrophilicities, and Protecting Group Abilities of Phenylfluorenylium and Tritylium Ions." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 23,3 (2017): 623-630. doi: https://doi.org/10.1002/chem.201603963
Follet E, Mayer P, Berionni G. Structures, Lewis Acidities, Electrophilicities, and Protecting Group Abilities of Phenylfluorenylium and Tritylium Ions. Chemistry. 2017 Jan 12;23(3):623-630. doi: 10.1002/chem.201603963. Epub 2016 Dec 05. PMID: 27723164.
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Stereospecific Allylic Functionalization: The Reactions of Allylboronate Complexes with Electrophiles.

Journal of the American Chemical Society

García-Ruiz C, Chen JL, Sandford C, Feeney K, Lorenzo P, Berionni G, Mayr H, Aggarwal VK.
PMID: 29028321
J Am Chem Soc. 2017 Nov 01;139(43):15324-15327. doi: 10.1021/jacs.7b10240. Epub 2017 Oct 20.

Allylboronic esters react readily with carbonyls and imines (π-electrophiles), but are unreactive toward a range of other electrophiles. By addition of an aryllithium, the corresponding allylboronate complexes display enhanced nucleophilicity, enabling addition to a range of electrophiles (tropylium, benzodithiolylium,...

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García-Ruiz C, Chen JL, Sandford C, et al. Stereospecific Allylic Functionalization: The Reactions of Allylboronate Complexes with Electrophiles. J Am Chem Soc. 2017;139(43):15324-15327doi: 10.1021/jacs.7b10240.
García-Ruiz, C., Chen, J. L., Sandford, C., Feeney, K., Lorenzo, P., Berionni, G., Mayr, H., & Aggarwal, V. K. (2017). Stereospecific Allylic Functionalization: The Reactions of Allylboronate Complexes with Electrophiles. Journal of the American Chemical Society, 139(43), 15324-15327. https://doi.org/10.1021/jacs.7b10240
García-Ruiz, Cristina, et al. "Stereospecific Allylic Functionalization: The Reactions of Allylboronate Complexes with Electrophiles." Journal of the American Chemical Society vol. 139,43 (2017): 15324-15327. doi: https://doi.org/10.1021/jacs.7b10240
García-Ruiz C, Chen JL, Sandford C, Feeney K, Lorenzo P, Berionni G, Mayr H, Aggarwal VK. Stereospecific Allylic Functionalization: The Reactions of Allylboronate Complexes with Electrophiles. J Am Chem Soc. 2017 Nov 01;139(43):15324-15327. doi: 10.1021/jacs.7b10240. Epub 2017 Oct 20. PMID: 29028321; PMCID: PMC5682599.
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Rhodium-Catalyzed Direct Bis-cyanation of Arylimidazo[1,2-α]pyridine via Double C-H Activation.

The Journal of organic chemistry

Zhu X, Shen XJ, Tian ZY, Lu S, Tian LL, Liu WB, Song B, Hao XQ.
PMID: 28581299
J Org Chem. 2017 Jun 16;82(12):6022-6031. doi: 10.1021/acs.joc.6b03036. Epub 2017 Jun 05.

An efficient Cp*Rh(III)-catalyzed selective bis-cyanation of arylimidazo[1,2-α]pyridines with N-cyano-N-phenyl-p-methylbenzenesulfonamide via N-directed ortho double C-H activation has been developed. The reaction proceeds with broad functional group tolerance to furnish various cyanated imidazopyridines in high yields. The current methodology exhibits unique...

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Zhu X, Shen XJ, Tian ZY, et al. Rhodium-Catalyzed Direct Bis-cyanation of Arylimidazo[1,2-α]pyridine via Double C-H Activation. J Org Chem. 2017;82(12):6022-6031doi: 10.1021/acs.joc.6b03036.
Zhu, X., Shen, X. J., Tian, Z. Y., Lu, S., Tian, L. L., Liu, W. B., Song, B., & Hao, X. Q. (2017). Rhodium-Catalyzed Direct Bis-cyanation of Arylimidazo[1,2-α]pyridine via Double C-H Activation. The Journal of organic chemistry, 82(12), 6022-6031. https://doi.org/10.1021/acs.joc.6b03036
Zhu, Xinju, et al. "Rhodium-Catalyzed Direct Bis-cyanation of Arylimidazo[1,2-α]pyridine via Double C-H Activation." The Journal of organic chemistry vol. 82,12 (2017): 6022-6031. doi: https://doi.org/10.1021/acs.joc.6b03036
Zhu X, Shen XJ, Tian ZY, Lu S, Tian LL, Liu WB, Song B, Hao XQ. Rhodium-Catalyzed Direct Bis-cyanation of Arylimidazo[1,2-α]pyridine via Double C-H Activation. J Org Chem. 2017 Jun 16;82(12):6022-6031. doi: 10.1021/acs.joc.6b03036. Epub 2017 Jun 05. PMID: 28581299.
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Triazole-Based Anion-Binding Catalysis for the Enantioselective Dearomatization of N-Heteroarenes with Phosphorus Nucleophiles.

Chemistry (Weinheim an der Bergstrasse, Germany)

Fischer T, Duong QN, García Mancheño O.
PMID: 28111819
Chemistry. 2017 May 02;23(25):5983-5987. doi: 10.1002/chem.201605660. Epub 2017 Feb 16.

The first enantioselective synthesis of chiral heterocyclic α-amino phosphonates by nucleophilic dearomatization of quinolines and pyridines using an anion-binding organocatalysis approach is described. Chiral tetrakistriazoles were employed as efficient hydrogen-bond donor catalysts by forming a chiral close ion-pair with...

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Fischer T, Duong QN, García Mancheño O. Triazole-Based Anion-Binding Catalysis for the Enantioselective Dearomatization of N-Heteroarenes with Phosphorus Nucleophiles. Chemistry. 2017;23(25):5983-5987doi: 10.1002/chem.201605660.
Fischer, T., Duong, Q. N., & García Mancheño, O. (2017). Triazole-Based Anion-Binding Catalysis for the Enantioselective Dearomatization of N-Heteroarenes with Phosphorus Nucleophiles. Chemistry (Weinheim an der Bergstrasse, Germany), 23(25), 5983-5987. https://doi.org/10.1002/chem.201605660
Fischer, Theresa, et al. "Triazole-Based Anion-Binding Catalysis for the Enantioselective Dearomatization of N-Heteroarenes with Phosphorus Nucleophiles." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 23,25 (2017): 5983-5987. doi: https://doi.org/10.1002/chem.201605660
Fischer T, Duong QN, García Mancheño O. Triazole-Based Anion-Binding Catalysis for the Enantioselective Dearomatization of N-Heteroarenes with Phosphorus Nucleophiles. Chemistry. 2017 May 02;23(25):5983-5987. doi: 10.1002/chem.201605660. Epub 2017 Feb 16. PMID: 28111819.
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Functional conjugated pyridines via main-group element tuning.

Chemical communications (Cambridge, England)

Stolar M, Baumgartner T.
PMID: 29517790
Chem Commun (Camb). 2018 Mar 29;54(27):3311-3322. doi: 10.1039/c8cc00373d.

Pyridine-based materials have seen widespread attention for the development of n-type organic materials. In recent years, the incorporation of main-group elements has also explored significant advantages for the development and tunability of organic conjugated materials. The unique chemical and...

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Stolar M, Baumgartner T. Functional conjugated pyridines via main-group element tuning. Chem Commun (Camb). 2018;54(27):3311-3322doi: 10.1039/c8cc00373d.
Stolar, M., & Baumgartner, T. (2018). Functional conjugated pyridines via main-group element tuning. Chemical communications (Cambridge, England), 54(27), 3311-3322. https://doi.org/10.1039/c8cc00373d
Stolar, Monika, and Baumgartner, Thomas. "Functional conjugated pyridines via main-group element tuning." Chemical communications (Cambridge, England) vol. 54,27 (2018): 3311-3322. doi: https://doi.org/10.1039/c8cc00373d
Stolar M, Baumgartner T. Functional conjugated pyridines via main-group element tuning. Chem Commun (Camb). 2018 Mar 29;54(27):3311-3322. doi: 10.1039/c8cc00373d. PMID: 29517790.
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Vertically-expanded imidazo[1,2-a]pyridines and imidazo[1,5-a]pyridine via dehydrogenative coupling.

Organic & biomolecular chemistry

Firmansyah D, Banasiewicz M, Gryko DT.
PMID: 25452099
Org Biomol Chem. 2015 Feb 07;13(5):1367-74. doi: 10.1039/c4ob02383h.

The anion-radical coupling of structurally diverse series of aromatic compounds possessing biaryl linkages led to seven fused, polycyclic heterocycles in reasonable yields. The yield of the key step (K, toluene, O2) depends on both electronic and steric factors. The...

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Firmansyah D, Banasiewicz M, Gryko DT. Vertically-expanded imidazo[1,2-a]pyridines and imidazo[1,5-a]pyridine via dehydrogenative coupling. Org Biomol Chem. 2015;13(5):1367-74doi: 10.1039/c4ob02383h.
Firmansyah, D., Banasiewicz, M., & Gryko, D. T. (2015). Vertically-expanded imidazo[1,2-a]pyridines and imidazo[1,5-a]pyridine via dehydrogenative coupling. Organic & biomolecular chemistry, 13(5), 1367-74. https://doi.org/10.1039/c4ob02383h
Firmansyah, Dikhi, et al. "Vertically-expanded imidazo[1,2-a]pyridines and imidazo[1,5-a]pyridine via dehydrogenative coupling." Organic & biomolecular chemistry vol. 13,5 (2015): 1367-74. doi: https://doi.org/10.1039/c4ob02383h
Firmansyah D, Banasiewicz M, Gryko DT. Vertically-expanded imidazo[1,2-a]pyridines and imidazo[1,5-a]pyridine via dehydrogenative coupling. Org Biomol Chem. 2015 Feb 07;13(5):1367-74. doi: 10.1039/c4ob02383h. PMID: 25452099.
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Au-catalyzed ring-opening reactions of 2-(1-alkynyl-cyclopropyl)pyridines with nucleophiles.

Organic & biomolecular chemistry

Liu RR, Ye SC, Lu CJ, Xiang B, Gao J, Jia YX.
PMID: 25832795
Org Biomol Chem. 2015 May 07;13(17):4855-8. doi: 10.1039/c5ob00523j.

A novel method for the C-C bond cleavage of cyclopropanes was developed by gold-catalyzed cycloisomerization of 2-(1-alkynyl-cyclopropyl)pyridine with nucleophiles, which provides efficient access to structurally diverse indolizines under mild conditions. A series of N-, C- and O-based nucleophiles were...

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Liu RR, Ye SC, Lu CJ, et al. Au-catalyzed ring-opening reactions of 2-(1-alkynyl-cyclopropyl)pyridines with nucleophiles. Org Biomol Chem. 2015;13(17):4855-8doi: 10.1039/c5ob00523j.
Liu, R. R., Ye, S. C., Lu, C. J., Xiang, B., Gao, J., & Jia, Y. X. (2015). Au-catalyzed ring-opening reactions of 2-(1-alkynyl-cyclopropyl)pyridines with nucleophiles. Organic & biomolecular chemistry, 13(17), 4855-8. https://doi.org/10.1039/c5ob00523j
Liu, Ren-Rong, et al. "Au-catalyzed ring-opening reactions of 2-(1-alkynyl-cyclopropyl)pyridines with nucleophiles." Organic & biomolecular chemistry vol. 13,17 (2015): 4855-8. doi: https://doi.org/10.1039/c5ob00523j
Liu RR, Ye SC, Lu CJ, Xiang B, Gao J, Jia YX. Au-catalyzed ring-opening reactions of 2-(1-alkynyl-cyclopropyl)pyridines with nucleophiles. Org Biomol Chem. 2015 May 07;13(17):4855-8. doi: 10.1039/c5ob00523j. PMID: 25832795.
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