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Recent advances in [2+2+2] cycloaddition reactions.

Chemical Society reviews

Domínguez G, Pérez-Castells J.
PMID: 21431173
Chem Soc Rev. 2011 Jul;40(7):3430-44. doi: 10.1039/c1cs15029d. Epub 2011 Mar 23.

The [2+2+2] cycloaddition is an elegant, atom-efficient and group tolerant process for the synthesis of carbo- and heterocycles, mostly aromatic, involving the formation of several C-C bonds in a single step. Cyclotrimerisation is catalyzed by a variety of organometallic...

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Domínguez G, Pérez-Castells J. Recent advances in [2+2+2] cycloaddition reactions. Chem Soc Rev. 2011;40(7):3430-44doi: 10.1039/c1cs15029d.
Domínguez, G., & Pérez-Castells, J. (2011). Recent advances in [2+2+2] cycloaddition reactions. Chemical Society reviews, 40(7), 3430-44. https://doi.org/10.1039/c1cs15029d
Domínguez, Gema, and Pérez-Castells, Javier. "Recent advances in [2+2+2] cycloaddition reactions." Chemical Society reviews vol. 40,7 (2011): 3430-44. doi: https://doi.org/10.1039/c1cs15029d
Domínguez G, Pérez-Castells J. Recent advances in [2+2+2] cycloaddition reactions. Chem Soc Rev. 2011 Jul;40(7):3430-44. doi: 10.1039/c1cs15029d. Epub 2011 Mar 23. PMID: 21431173.
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Copper-catalyzed decarboxylative cross-coupling of cinnamic acids and ACCN via single electron transfer.

Organic & biomolecular chemistry

Gao B, Xie Y, Yang L, Huang H.
PMID: 26837658
Org Biomol Chem. 2016 Feb 28;14(8):2399-402. doi: 10.1039/c5ob02677f. Epub 2016 Feb 03.

A novel and convenient method for the synthesis of β,γ-unsaturated nitriles using ACCN (1,1'-azobis(cyclohexane-1-carbonitrile)) as a cyano source was described. This reaction was amenable to a broad range of substrates and provided the desired β,γ-unsaturated nitriles containing an all-carbon...

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Gao B, Xie Y, Yang L, et al. Copper-catalyzed decarboxylative cross-coupling of cinnamic acids and ACCN via single electron transfer. Org Biomol Chem. 2016;14(8):2399-402doi: 10.1039/c5ob02677f.
Gao, B., Xie, Y., Yang, L., & Huang, H. (2016). Copper-catalyzed decarboxylative cross-coupling of cinnamic acids and ACCN via single electron transfer. Organic & biomolecular chemistry, 14(8), 2399-402. https://doi.org/10.1039/c5ob02677f
Gao, Bao, et al. "Copper-catalyzed decarboxylative cross-coupling of cinnamic acids and ACCN via single electron transfer." Organic & biomolecular chemistry vol. 14,8 (2016): 2399-402. doi: https://doi.org/10.1039/c5ob02677f
Gao B, Xie Y, Yang L, Huang H. Copper-catalyzed decarboxylative cross-coupling of cinnamic acids and ACCN via single electron transfer. Org Biomol Chem. 2016 Feb 28;14(8):2399-402. doi: 10.1039/c5ob02677f. Epub 2016 Feb 03. PMID: 26837658.
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Pd-Catalyzed Intramolecular Cyclization via Direct C-H Addition to Nitriles: Skeletal Diverse Synthesis of Fused Polycyclic Indoles.

Organic letters

Wang TT, Zhao L, Zhang YJ, Liao WW.
PMID: 27626643
Org Lett. 2016 Oct 07;18(19):5002-5005. doi: 10.1021/acs.orglett.6b02460. Epub 2016 Sep 14.

The first example of Pd-catalyzed intramolecular C-H addition of indoles bearing cyanohydrin components at the C(3), C(2), and N(1) positions to nitriles is described. A wide range of functionalized partially saturated carbazoles, tetrahydropyrido[1,2-a]indole, and carbazoles can be prepared in...

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Wang TT, Zhao L, Zhang YJ, et al. Pd-Catalyzed Intramolecular Cyclization via Direct C-H Addition to Nitriles: Skeletal Diverse Synthesis of Fused Polycyclic Indoles. Org Lett. 2016;18(19):5002-5005doi: 10.1021/acs.orglett.6b02460.
Wang, T. T., Zhao, L., Zhang, Y. J., & Liao, W. W. (2016). Pd-Catalyzed Intramolecular Cyclization via Direct C-H Addition to Nitriles: Skeletal Diverse Synthesis of Fused Polycyclic Indoles. Organic letters, 18(19), 5002-5005. https://doi.org/10.1021/acs.orglett.6b02460
Wang, Ting-Ting, et al. "Pd-Catalyzed Intramolecular Cyclization via Direct C-H Addition to Nitriles: Skeletal Diverse Synthesis of Fused Polycyclic Indoles." Organic letters vol. 18,19 (2016): 5002-5005. doi: https://doi.org/10.1021/acs.orglett.6b02460
Wang TT, Zhao L, Zhang YJ, Liao WW. Pd-Catalyzed Intramolecular Cyclization via Direct C-H Addition to Nitriles: Skeletal Diverse Synthesis of Fused Polycyclic Indoles. Org Lett. 2016 Oct 07;18(19):5002-5005. doi: 10.1021/acs.orglett.6b02460. Epub 2016 Sep 14. PMID: 27626643.
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Asymmetric Hydrogenation of β-Aryloxy/Alkoxy Cinnamic Nitriles and Esters.

Organic letters

Kong D, Li M, Wang R, Zi G, Hou G.
PMID: 27626807
Org Lett. 2016 Oct 07;18(19):4916-4919. doi: 10.1021/acs.orglett.6b02393. Epub 2016 Sep 14.

A highly efficient and enantioselective hydrogenation of β-aryloxy/alkoxy cinnamic nitriles and esters under mild conditions has been realized by using a rhodium catalyst with a chiral f-spiroPhos ligand. The method provides efficient access to the asymmetric synthesis of a...

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Kong D, Li M, Wang R, et al. Asymmetric Hydrogenation of β-Aryloxy/Alkoxy Cinnamic Nitriles and Esters. Org Lett. 2016;18(19):4916-4919doi: 10.1021/acs.orglett.6b02393.
Kong, D., Li, M., Wang, R., Zi, G., & Hou, G. (2016). Asymmetric Hydrogenation of β-Aryloxy/Alkoxy Cinnamic Nitriles and Esters. Organic letters, 18(19), 4916-4919. https://doi.org/10.1021/acs.orglett.6b02393
Kong, Duanyang, et al. "Asymmetric Hydrogenation of β-Aryloxy/Alkoxy Cinnamic Nitriles and Esters." Organic letters vol. 18,19 (2016): 4916-4919. doi: https://doi.org/10.1021/acs.orglett.6b02393
Kong D, Li M, Wang R, Zi G, Hou G. Asymmetric Hydrogenation of β-Aryloxy/Alkoxy Cinnamic Nitriles and Esters. Org Lett. 2016 Oct 07;18(19):4916-4919. doi: 10.1021/acs.orglett.6b02393. Epub 2016 Sep 14. PMID: 27626807.
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PS-BEMP as a basic catalyst for the phospha-Michael addition to electron-poor alkenes.

Organic & biomolecular chemistry

Strappaveccia G, Bianchi L, Ziarelli S, Santoro S, Lanari D, Pizzo F, Vaccaro L.
PMID: 26974873
Org Biomol Chem. 2016 Apr 14;14(14):3521-5. doi: 10.1039/c6ob00242k. Epub 2016 Mar 14.

PS-BEMP was used as a heterogeneous catalyst for the phospha-Michael addition of phosphorus nucleophiles to a variety of electron-poor alkenes. The addition reactions were generally performed with equimolar amounts of reagents under solvent free conditions. The protocol proved to...

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Strappaveccia G, Bianchi L, Ziarelli S, et al. PS-BEMP as a basic catalyst for the phospha-Michael addition to electron-poor alkenes. Org Biomol Chem. 2016;14(14):3521-5doi: 10.1039/c6ob00242k.
Strappaveccia, G., Bianchi, L., Ziarelli, S., Santoro, S., Lanari, D., Pizzo, F., & Vaccaro, L. (2016). PS-BEMP as a basic catalyst for the phospha-Michael addition to electron-poor alkenes. Organic & biomolecular chemistry, 14(14), 3521-5. https://doi.org/10.1039/c6ob00242k
Strappaveccia, Giacomo, et al. "PS-BEMP as a basic catalyst for the phospha-Michael addition to electron-poor alkenes." Organic & biomolecular chemistry vol. 14,14 (2016): 3521-5. doi: https://doi.org/10.1039/c6ob00242k
Strappaveccia G, Bianchi L, Ziarelli S, Santoro S, Lanari D, Pizzo F, Vaccaro L. PS-BEMP as a basic catalyst for the phospha-Michael addition to electron-poor alkenes. Org Biomol Chem. 2016 Apr 14;14(14):3521-5. doi: 10.1039/c6ob00242k. Epub 2016 Mar 14. PMID: 26974873.
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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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Characterization of Tetracyanopyridine (TCNPy)-Based Magnets: V[TCNPy]2 ⋅z (CH2 Cl2 ) (Tc =111 K) and V[TCNPy]3 ⋅z (CH2 Cl2 ) (Tc =90 K).

Chemistry (Weinheim an der Bergstrasse, Germany)

Hao J, Davidson RA, Kareis CM, Kavand M, van Schooten KJ, Boehme C, Wöß E, Knör G, Miller JS.
PMID: 27529664
Chemistry. 2016 Sep 26;22(40):14273-8. doi: 10.1002/chem.201602385. Epub 2016 Aug 16.

The reaction of 2,3,5,6-tetracyanopyridine (TCNPy) with V(CO)6 in CH2 Cl2 forms new organic-based magnets of V[TCNPy]x ⋅z (CH2 Cl2 ) (x=2, 3) composition. Analysis of the IR spectra suggests that the TCNPy is reduced and coordinated to V(II) sites...

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Hao J, Davidson RA, Kareis CM, et al. Characterization of Tetracyanopyridine (TCNPy)-Based Magnets: V[TCNPy]2 ⋅z (CH2 Cl2 ) (Tc =111 K) and V[TCNPy]3 ⋅z (CH2 Cl2 ) (Tc =90 K). Chemistry. 2016;22(40):14273-8doi: 10.1002/chem.201602385.
Hao, J., Davidson, R. A., Kareis, C. M., Kavand, M., van Schooten, K. J., Boehme, C., Wöß, E., Knör, G., & Miller, J. S. (2016). Characterization of Tetracyanopyridine (TCNPy)-Based Magnets: V[TCNPy]2 ⋅z (CH2 Cl2 ) (Tc =111 K) and V[TCNPy]3 ⋅z (CH2 Cl2 ) (Tc =90 K). Chemistry (Weinheim an der Bergstrasse, Germany), 22(40), 14273-8. https://doi.org/10.1002/chem.201602385
Hao, Jingjun, et al. "Characterization of Tetracyanopyridine (TCNPy)-Based Magnets: V[TCNPy]2 ⋅z (CH2 Cl2 ) (Tc =111 K) and V[TCNPy]3 ⋅z (CH2 Cl2 ) (Tc =90 K)." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,40 (2016): 14273-8. doi: https://doi.org/10.1002/chem.201602385
Hao J, Davidson RA, Kareis CM, Kavand M, van Schooten KJ, Boehme C, Wöß E, Knör G, Miller JS. Characterization of Tetracyanopyridine (TCNPy)-Based Magnets: V[TCNPy]2 ⋅z (CH2 Cl2 ) (Tc =111 K) and V[TCNPy]3 ⋅z (CH2 Cl2 ) (Tc =90 K). Chemistry. 2016 Sep 26;22(40):14273-8. doi: 10.1002/chem.201602385. Epub 2016 Aug 16. PMID: 27529664.
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Diastereoselective Ritter-like Reaction on Cyclic Trifluoromethylated N,O-Acetals Derived from l-Tartaric Acid.

The Journal of organic chemistry

Ben Jamaa A, Grellepois F.
PMID: 28885838
J Org Chem. 2017 Oct 06;82(19):10360-10375. doi: 10.1021/acs.joc.7b01814. Epub 2017 Sep 08.

Despite the presence of the highly electron-withdrawing fluorinated substituent, cyclic α-trifluoromethylated N-acyliminium ions were successfully generated from fluorinated O-acetyl-N,O-acetal l-tartaric acid derivatives. The addition of nitriles on these intermediates occurred with high to excellent syn diastereoselectivity and led, in...

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Ben Jamaa A, Grellepois F. Diastereoselective Ritter-like Reaction on Cyclic Trifluoromethylated N,O-Acetals Derived from l-Tartaric Acid. J Org Chem. 2017;82(19):10360-10375doi: 10.1021/acs.joc.7b01814.
Ben Jamaa, A., & Grellepois, F. (2017). Diastereoselective Ritter-like Reaction on Cyclic Trifluoromethylated N,O-Acetals Derived from l-Tartaric Acid. The Journal of organic chemistry, 82(19), 10360-10375. https://doi.org/10.1021/acs.joc.7b01814
Ben Jamaa, Abdelkhalek, and Grellepois, Fabienne. "Diastereoselective Ritter-like Reaction on Cyclic Trifluoromethylated N,O-Acetals Derived from l-Tartaric Acid." The Journal of organic chemistry vol. 82,19 (2017): 10360-10375. doi: https://doi.org/10.1021/acs.joc.7b01814
Ben Jamaa A, Grellepois F. Diastereoselective Ritter-like Reaction on Cyclic Trifluoromethylated N,O-Acetals Derived from l-Tartaric Acid. J Org Chem. 2017 Oct 06;82(19):10360-10375. doi: 10.1021/acs.joc.7b01814. Epub 2017 Sep 08. PMID: 28885838.
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Sequential Oxidative α-Cyanation/Anti-Markovnikov Hydroalkoxylation of Allylamines.

Organic letters

Wagner A, Hampel N, Zipse H, Ofial AR.
PMID: 26372780
Org Lett. 2015 Oct 02;17(19):4770-3. doi: 10.1021/acs.orglett.5b02319.

Iron-catalyzed oxidative α-cyanations at tertiary allylamines in the allylic position are followed by anti-Markovnikov additions of alcohols across the vinylic CC double bonds of the initially generated α-amino nitriles. These consecutive reactions generate 2-amino-4-alkoxybutanenitriles from three reactants (allylamines, trimethylsilyl...

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Wagner A, Hampel N, Zipse H, et al. Sequential Oxidative α-Cyanation/Anti-Markovnikov Hydroalkoxylation of Allylamines. Org Lett. 2015;17(19):4770-3doi: 10.1021/acs.orglett.5b02319.
Wagner, A., Hampel, N., Zipse, H., & Ofial, A. R. (2015). Sequential Oxidative α-Cyanation/Anti-Markovnikov Hydroalkoxylation of Allylamines. Organic letters, 17(19), 4770-3. https://doi.org/10.1021/acs.orglett.5b02319
Wagner, Alexander, et al. "Sequential Oxidative α-Cyanation/Anti-Markovnikov Hydroalkoxylation of Allylamines." Organic letters vol. 17,19 (2015): 4770-3. doi: https://doi.org/10.1021/acs.orglett.5b02319
Wagner A, Hampel N, Zipse H, Ofial AR. Sequential Oxidative α-Cyanation/Anti-Markovnikov Hydroalkoxylation of Allylamines. Org Lett. 2015 Oct 02;17(19):4770-3. doi: 10.1021/acs.orglett.5b02319. PMID: 26372780.
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Organic Covalent Patterning of Nanostructured Graphene with Selectivity at the Atomic Level.

Nano letters

Navarro JJ, Leret S, Calleja F, Stradi D, Black A, Bernardo-Gavito R, Garnica M, Granados D, Vázquez de Parga AL, Pérez EM, Miranda R.
PMID: 26624843
Nano Lett. 2016 Jan 13;16(1):355-61. doi: 10.1021/acs.nanolett.5b03928. Epub 2015 Dec 02.

Organic covalent functionalization of graphene with long-range periodicity is highly desirable-it is anticipated to provide control over its electronic, optical, or magnetic properties-and remarkably challenging. In this work we describe a method for the covalent modification of graphene with...

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Navarro JJ, Leret S, Calleja F, et al. Organic Covalent Patterning of Nanostructured Graphene with Selectivity at the Atomic Level. Nano Lett. 2015;16(1):355-61doi: 10.1021/acs.nanolett.5b03928.
Navarro, J. J., Leret, S., Calleja, F., Stradi, D., Black, A., Bernardo-Gavito, R., Garnica, M., Granados, D., Vázquez de Parga, A. L., Pérez, E. M., & Miranda, R. (2016). Organic Covalent Patterning of Nanostructured Graphene with Selectivity at the Atomic Level. Nano letters, 16(1), 355-61. https://doi.org/10.1021/acs.nanolett.5b03928
Navarro, Juan Jesús, et al. "Organic Covalent Patterning of Nanostructured Graphene with Selectivity at the Atomic Level." Nano letters vol. 16,1 (2016): 355-61. doi: https://doi.org/10.1021/acs.nanolett.5b03928
Navarro JJ, Leret S, Calleja F, Stradi D, Black A, Bernardo-Gavito R, Garnica M, Granados D, Vázquez de Parga AL, Pérez EM, Miranda R. Organic Covalent Patterning of Nanostructured Graphene with Selectivity at the Atomic Level. Nano Lett. 2016 Jan 13;16(1):355-61. doi: 10.1021/acs.nanolett.5b03928. Epub 2015 Dec 02. PMID: 26624843.
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A versatile tripodal Cu(I) reagent for C-N bond construction via nitrene-transfer chemistry: catalytic perspectives and mechanistic insights on C-H aminations/amidinations and olefin aziridinations.

Journal of the American Chemical Society

Bagchi V, Paraskevopoulou P, Das P, Chi L, Wang Q, Choudhury A, Mathieson JS, Cronin L, Pardue DB, Cundari TR, Mitrikas G, Sanakis Y, Stavropoulos P.
PMID: 25025754
J Am Chem Soc. 2014 Aug 13;136(32):11362-81. doi: 10.1021/ja503869j. Epub 2014 Aug 05.

A Cu(I) catalyst (1), supported by a framework of strongly basic guanidinato moieties, mediates nitrene-transfer from PhI═NR sources to a wide variety of aliphatic hydrocarbons (C-H amination or amidination in the presence of nitriles) and olefins (aziridination). Product profiles...

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Bagchi V, Paraskevopoulou P, Das P, et al. A versatile tripodal Cu(I) reagent for C-N bond construction via nitrene-transfer chemistry: catalytic perspectives and mechanistic insights on C-H aminations/amidinations and olefin aziridinations. J Am Chem Soc. 2014;136(32):11362-81doi: 10.1021/ja503869j.
Bagchi, V., Paraskevopoulou, P., Das, P., Chi, L., Wang, Q., Choudhury, A., Mathieson, J. S., Cronin, L., Pardue, D. B., Cundari, T. R., Mitrikas, G., Sanakis, Y., & Stavropoulos, P. (2014). A versatile tripodal Cu(I) reagent for C-N bond construction via nitrene-transfer chemistry: catalytic perspectives and mechanistic insights on C-H aminations/amidinations and olefin aziridinations. Journal of the American Chemical Society, 136(32), 11362-81. https://doi.org/10.1021/ja503869j
Bagchi, Vivek, et al. "A versatile tripodal Cu(I) reagent for C-N bond construction via nitrene-transfer chemistry: catalytic perspectives and mechanistic insights on C-H aminations/amidinations and olefin aziridinations." Journal of the American Chemical Society vol. 136,32 (2014): 11362-81. doi: https://doi.org/10.1021/ja503869j
Bagchi V, Paraskevopoulou P, Das P, Chi L, Wang Q, Choudhury A, Mathieson JS, Cronin L, Pardue DB, Cundari TR, Mitrikas G, Sanakis Y, Stavropoulos P. A versatile tripodal Cu(I) reagent for C-N bond construction via nitrene-transfer chemistry: catalytic perspectives and mechanistic insights on C-H aminations/amidinations and olefin aziridinations. J Am Chem Soc. 2014 Aug 13;136(32):11362-81. doi: 10.1021/ja503869j. Epub 2014 Aug 05. PMID: 25025754.
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Activation of alcohols with carbon dioxide: intermolecular allylation of weakly acidic pronucleophiles.

Organic letters

Lang SB, Locascio TM, Tunge JA.
PMID: 25089846
Org Lett. 2014 Aug 15;16(16):4308-11. doi: 10.1021/ol502023d. Epub 2014 Aug 04.

The direct coupling of allyl alcohols with nitroalkanes, nitriles, and aldehydes using catalytic Pd(PPh3)4 has been accomplished via activation of C-OH bonds with CO2. The in situ formation of carbonates from alcohols and CO2 facilitates oxidative addition to Pd...

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Lang SB, Locascio TM, Tunge JA. Activation of alcohols with carbon dioxide: intermolecular allylation of weakly acidic pronucleophiles. Org Lett. 2014;16(16):4308-11doi: 10.1021/ol502023d.
Lang, S. B., Locascio, T. M., & Tunge, J. A. (2014). Activation of alcohols with carbon dioxide: intermolecular allylation of weakly acidic pronucleophiles. Organic letters, 16(16), 4308-11. https://doi.org/10.1021/ol502023d
Lang, Simon B, et al. "Activation of alcohols with carbon dioxide: intermolecular allylation of weakly acidic pronucleophiles." Organic letters vol. 16,16 (2014): 4308-11. doi: https://doi.org/10.1021/ol502023d
Lang SB, Locascio TM, Tunge JA. Activation of alcohols with carbon dioxide: intermolecular allylation of weakly acidic pronucleophiles. Org Lett. 2014 Aug 15;16(16):4308-11. doi: 10.1021/ol502023d. Epub 2014 Aug 04. PMID: 25089846; PMCID: PMC4136682.
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