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Copper-Catalyzed Cyanation of N-Tosylhydrazones with Thiocyanate Salt as the "CN" Source.

The Journal of organic chemistry

Huang Y, Yu Y, Zhu Z, Zhu C, Cen J, Li X, Wu W, Jiang H.
PMID: 28656758
J Org Chem. 2017 Jul 21;82(14):7621-7627. doi: 10.1021/acs.joc.7b00836. Epub 2017 Jul 10.

A novel protocol for the synthesis of α-aryl nitriles has been successfully achieved via a copper-catalyzed cyanation of N-tosylhydrazones employing thiocyanate as the source of cyanide. The features of this method include a convenient operation, readily available substrates, low-toxicity...

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Huang Y, Yu Y, Zhu Z, et al. Copper-Catalyzed Cyanation of N-Tosylhydrazones with Thiocyanate Salt as the "CN" Source. J Org Chem. 2017;82(14):7621-7627doi: 10.1021/acs.joc.7b00836.
Huang, Y., Yu, Y., Zhu, Z., Zhu, C., Cen, J., Li, X., Wu, W., & Jiang, H. (2017). Copper-Catalyzed Cyanation of N-Tosylhydrazones with Thiocyanate Salt as the "CN" Source. The Journal of organic chemistry, 82(14), 7621-7627. https://doi.org/10.1021/acs.joc.7b00836
Huang, Yubing, et al. "Copper-Catalyzed Cyanation of N-Tosylhydrazones with Thiocyanate Salt as the "CN" Source." The Journal of organic chemistry vol. 82,14 (2017): 7621-7627. doi: https://doi.org/10.1021/acs.joc.7b00836
Huang Y, Yu Y, Zhu Z, Zhu C, Cen J, Li X, Wu W, Jiang H. Copper-Catalyzed Cyanation of N-Tosylhydrazones with Thiocyanate Salt as the "CN" Source. J Org Chem. 2017 Jul 21;82(14):7621-7627. doi: 10.1021/acs.joc.7b00836. Epub 2017 Jul 10. PMID: 28656758.
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Catalytic Enantioselective Reaction of α-Phenylthioacetonitriles with Imines Using Chiral Bis(imidazoline)-Palladium Catalysts.

Chemistry (Weinheim an der Bergstrasse, Germany)

Kondo M, Kobayashi N, Hatanaka T, Funahashi Y, Nakamura S.
PMID: 25965425
Chemistry. 2015 Jun 15;21(25):9066-70. doi: 10.1002/chem.201501351. Epub 2015 May 12.

The catalytic enantioselective reaction of α-phenylthioacetonitriles with imines has been developed. The reaction of various imines proceeds in good yields and diastereo- and enantioselectivities in the presence of chiral bis(imidazoline)-palladium catalysts. The obtained products can be converted into β-aminonitrile...

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Kondo M, Kobayashi N, Hatanaka T, et al. Catalytic Enantioselective Reaction of α-Phenylthioacetonitriles with Imines Using Chiral Bis(imidazoline)-Palladium Catalysts. Chemistry. 2015;21(25):9066-70doi: 10.1002/chem.201501351.
Kondo, M., Kobayashi, N., Hatanaka, T., Funahashi, Y., & Nakamura, S. (2015). Catalytic Enantioselective Reaction of α-Phenylthioacetonitriles with Imines Using Chiral Bis(imidazoline)-Palladium Catalysts. Chemistry (Weinheim an der Bergstrasse, Germany), 21(25), 9066-70. https://doi.org/10.1002/chem.201501351
Kondo, Masaru, et al. "Catalytic Enantioselective Reaction of α-Phenylthioacetonitriles with Imines Using Chiral Bis(imidazoline)-Palladium Catalysts." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,25 (2015): 9066-70. doi: https://doi.org/10.1002/chem.201501351
Kondo M, Kobayashi N, Hatanaka T, Funahashi Y, Nakamura S. Catalytic Enantioselective Reaction of α-Phenylthioacetonitriles with Imines Using Chiral Bis(imidazoline)-Palladium Catalysts. Chemistry. 2015 Jun 15;21(25):9066-70. doi: 10.1002/chem.201501351. Epub 2015 May 12. PMID: 25965425.
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N-Heterocyclic Carbene-Catalyzed Diastereoselective Vinylogous Michael Addition Reaction of γ-Substituted Deconjugated Butenolides.

The Journal of organic chemistry

Guo H, Xing F, Du GF, Huang KW, Dai B, He L.
PMID: 26569552
J Org Chem. 2015 Dec 18;80(24):12606-13. doi: 10.1021/acs.joc.5b01845. Epub 2015 Nov 30.

An efficient N-heterocyclic carbene (NHC)-catalyzed vinylogous Michael addition of deconjugated butenolides was developed. In the presence of 5 mol % of the NHC catalyst, both γ-alkyl- and aryl-substituted deconjugated butenolides undergo vinylogous Michael addition with various α, β-unsaturated ketones,...

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Guo H, Xing F, Du GF, et al. N-Heterocyclic Carbene-Catalyzed Diastereoselective Vinylogous Michael Addition Reaction of γ-Substituted Deconjugated Butenolides. J Org Chem. 2015;80(24):12606-13doi: 10.1021/acs.joc.5b01845.
Guo, H., Xing, F., Du, G. F., Huang, K. W., Dai, B., & He, L. (2015). N-Heterocyclic Carbene-Catalyzed Diastereoselective Vinylogous Michael Addition Reaction of γ-Substituted Deconjugated Butenolides. The Journal of organic chemistry, 80(24), 12606-13. https://doi.org/10.1021/acs.joc.5b01845
Guo, Hao, et al. "N-Heterocyclic Carbene-Catalyzed Diastereoselective Vinylogous Michael Addition Reaction of γ-Substituted Deconjugated Butenolides." The Journal of organic chemistry vol. 80,24 (2015): 12606-13. doi: https://doi.org/10.1021/acs.joc.5b01845
Guo H, Xing F, Du GF, Huang KW, Dai B, He L. N-Heterocyclic Carbene-Catalyzed Diastereoselective Vinylogous Michael Addition Reaction of γ-Substituted Deconjugated Butenolides. J Org Chem. 2015 Dec 18;80(24):12606-13. doi: 10.1021/acs.joc.5b01845. Epub 2015 Nov 30. PMID: 26569552.
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Coupling of platinated triguanides with platinum-activated nitriles as a novel strategy for generation of dimetallic systems.

Dalton transactions (Cambridge, England : 2003)

Serebryanskaya TV, Novikov AS, Gushchin PV, Zolotarev AA, Gurzhiy VV, Kukushkin VY.
PMID: 25720690
Dalton Trans. 2015 Apr 07;44(13):6003-11. doi: 10.1039/c4dt03870c.

One of two Pt(IV)-activated propanenitriles in trans-[PtCl4(EtCN)2] is involved in platinum(IV)-mediated nitrile-imine coupling with the platinum(II)-based metallacycles [PtCl2{NH=C(NR2)N(Ph)C(=NH)N(Ph)C(NR2)=NH}] [R2 = Me2 (1a), C5H10 (1b)] yielding diplatinum products, whose structures depend on molar ratios between the reactants. At a 1...

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Serebryanskaya TV, Novikov AS, Gushchin PV, et al. Coupling of platinated triguanides with platinum-activated nitriles as a novel strategy for generation of dimetallic systems. Dalton Trans. 2015;44(13):6003-11doi: 10.1039/c4dt03870c.
Serebryanskaya, T. V., Novikov, A. S., Gushchin, P. V., Zolotarev, A. A., Gurzhiy, V. V., & Kukushkin, V. Y. (2015). Coupling of platinated triguanides with platinum-activated nitriles as a novel strategy for generation of dimetallic systems. Dalton transactions (Cambridge, England : 2003), 44(13), 6003-11. https://doi.org/10.1039/c4dt03870c
Serebryanskaya, Tatiyana V, et al. "Coupling of platinated triguanides with platinum-activated nitriles as a novel strategy for generation of dimetallic systems." Dalton transactions (Cambridge, England : 2003) vol. 44,13 (2015): 6003-11. doi: https://doi.org/10.1039/c4dt03870c
Serebryanskaya TV, Novikov AS, Gushchin PV, Zolotarev AA, Gurzhiy VV, Kukushkin VY. Coupling of platinated triguanides with platinum-activated nitriles as a novel strategy for generation of dimetallic systems. Dalton Trans. 2015 Apr 07;44(13):6003-11. doi: 10.1039/c4dt03870c. PMID: 25720690.
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An efficient ruthenium(IV) catalyst for the selective hydration of nitriles to amides in water under mild conditions.

Chemical communications (Cambridge, England)

Tomás-Mendivil E, Suárez FJ, Díez J, Cadierno V.
PMID: 25019325
Chem Commun (Camb). 2014 Sep 04;50(68):9661-4. doi: 10.1039/c4cc04058a.

A Ru(IV) catalyst able to promote the selective hydration of nitriles to amides in water, at low metal loadings and under mild conditions, is presented.

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Tomás-Mendivil E, Suárez FJ, Díez J, et al. An efficient ruthenium(IV) catalyst for the selective hydration of nitriles to amides in water under mild conditions. Chem Commun (Camb). 2014;50(68):9661-4doi: 10.1039/c4cc04058a.
Tomás-Mendivil, E., Suárez, F. J., Díez, J., & Cadierno, V. (2014). An efficient ruthenium(IV) catalyst for the selective hydration of nitriles to amides in water under mild conditions. Chemical communications (Cambridge, England), 50(68), 9661-4. https://doi.org/10.1039/c4cc04058a
Tomás-Mendivil, Eder, et al. "An efficient ruthenium(IV) catalyst for the selective hydration of nitriles to amides in water under mild conditions." Chemical communications (Cambridge, England) vol. 50,68 (2014): 9661-4. doi: https://doi.org/10.1039/c4cc04058a
Tomás-Mendivil E, Suárez FJ, Díez J, Cadierno V. An efficient ruthenium(IV) catalyst for the selective hydration of nitriles to amides in water under mild conditions. Chem Commun (Camb). 2014 Sep 04;50(68):9661-4. doi: 10.1039/c4cc04058a. PMID: 25019325.
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A radical anti-Markovnikov addition of alkyl nitriles to simple alkenes via selective sp(3) C-H bond functionalization.

Chemical communications (Cambridge, England)

Li Z, Xiao Y, Liu ZQ.
PMID: 25997410
Chem Commun (Camb). 2015 Jun 21;51(49):9969-71. doi: 10.1039/c5cc02968f.

An efficient hydrocyanoalkylation of unactivated alkenes with alkyl nitriles was developed. Through this free-radical-initiated selective activation of the α-C(sp(3))-H bond of acetonitriles, an anti-Markovnikov addition of an α-cyano C-centered radical to olefins has been achieved, which allows a facile...

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Li Z, Xiao Y, Liu ZQ. A radical anti-Markovnikov addition of alkyl nitriles to simple alkenes via selective sp(3) C-H bond functionalization. Chem Commun (Camb). 2015;51(49):9969-71doi: 10.1039/c5cc02968f.
Li, Z., Xiao, Y., & Liu, Z. Q. (2015). A radical anti-Markovnikov addition of alkyl nitriles to simple alkenes via selective sp(3) C-H bond functionalization. Chemical communications (Cambridge, England), 51(49), 9969-71. https://doi.org/10.1039/c5cc02968f
Li, Zejiang, et al. "A radical anti-Markovnikov addition of alkyl nitriles to simple alkenes via selective sp(3) C-H bond functionalization." Chemical communications (Cambridge, England) vol. 51,49 (2015): 9969-71. doi: https://doi.org/10.1039/c5cc02968f
Li Z, Xiao Y, Liu ZQ. A radical anti-Markovnikov addition of alkyl nitriles to simple alkenes via selective sp(3) C-H bond functionalization. Chem Commun (Camb). 2015 Jun 21;51(49):9969-71. doi: 10.1039/c5cc02968f. PMID: 25997410.
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Arylthio-metal exchange of α-arylthioalkanenitriles.

Organic letters

Nath D, Skilbeck MC, Coldham I, Fleming FF.
PMID: 24328754
Org Lett. 2014 Jan 03;16(1):62-5. doi: 10.1021/ol403020s. Epub 2013 Dec 12.

The addition of BuLi, Bu3MgLi, Et2ZnBuLi, or Me2CuLi to α-arylthioalkanenitriles triggers an arylthio-metal exchange. NMR spectroscopic analyses implicate organometallic attack on sulfur forming a three-coordinate sulfidate as the key intermediate. Electrophilic trapping affords tertiary and quaternary nitriles in high...

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Nath D, Skilbeck MC, Coldham I, et al. Arylthio-metal exchange of α-arylthioalkanenitriles. Org Lett. 2013;16(1):62-5doi: 10.1021/ol403020s.
Nath, D., Skilbeck, M. C., Coldham, I., & Fleming, F. F. (2014). Arylthio-metal exchange of α-arylthioalkanenitriles. Organic letters, 16(1), 62-5. https://doi.org/10.1021/ol403020s
Nath, Dinesh, et al. "Arylthio-metal exchange of α-arylthioalkanenitriles." Organic letters vol. 16,1 (2014): 62-5. doi: https://doi.org/10.1021/ol403020s
Nath D, Skilbeck MC, Coldham I, Fleming FF. Arylthio-metal exchange of α-arylthioalkanenitriles. Org Lett. 2014 Jan 03;16(1):62-5. doi: 10.1021/ol403020s. Epub 2013 Dec 12. PMID: 24328754.
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Transition-Metal-Free Deacylative Cleavage of Unstrained C(sp(3))-C(sp(2)) Bonds: Cyanide-Free Access to Aryl and Aliphatic Nitriles from Ketones and Aldehydes.

Organic letters

Ge JJ, Yao CZ, Wang MM, Zheng HX, Kang YB, Li Y.
PMID: 26704699
Org Lett. 2016 Jan 15;18(2):228-31. doi: 10.1021/acs.orglett.5b03367. Epub 2015 Dec 24.

A transition-metal-free deacylative C(sp(3))-C(sp(2)) bond cleavage for the synthetically practical oxidative amination of ketones and aldehydes to nitriles is first described, using cheap and commercially abundant NaNO2 as the oxidant and the nitrogen source. Various nitriles bearing aryl, heteroaryl,...

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Ge JJ, Yao CZ, Wang MM, et al. Transition-Metal-Free Deacylative Cleavage of Unstrained C(sp(3))-C(sp(2)) Bonds: Cyanide-Free Access to Aryl and Aliphatic Nitriles from Ketones and Aldehydes. Org Lett. 2015;18(2):228-31doi: 10.1021/acs.orglett.5b03367.
Ge, J. J., Yao, C. Z., Wang, M. M., Zheng, H. X., Kang, Y. B., & Li, Y. (2016). Transition-Metal-Free Deacylative Cleavage of Unstrained C(sp(3))-C(sp(2)) Bonds: Cyanide-Free Access to Aryl and Aliphatic Nitriles from Ketones and Aldehydes. Organic letters, 18(2), 228-31. https://doi.org/10.1021/acs.orglett.5b03367
Ge, Jing-Jie, et al. "Transition-Metal-Free Deacylative Cleavage of Unstrained C(sp(3))-C(sp(2)) Bonds: Cyanide-Free Access to Aryl and Aliphatic Nitriles from Ketones and Aldehydes." Organic letters vol. 18,2 (2016): 228-31. doi: https://doi.org/10.1021/acs.orglett.5b03367
Ge JJ, Yao CZ, Wang MM, Zheng HX, Kang YB, Li Y. Transition-Metal-Free Deacylative Cleavage of Unstrained C(sp(3))-C(sp(2)) Bonds: Cyanide-Free Access to Aryl and Aliphatic Nitriles from Ketones and Aldehydes. Org Lett. 2016 Jan 15;18(2):228-31. doi: 10.1021/acs.orglett.5b03367. Epub 2015 Dec 24. PMID: 26704699.
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Can Nitriles Be Stronger Bases Than Proton Sponges in the Gas Phase? A Computational Analysis.

The journal of physical chemistry. A

Raczyńska ED, Makowski M, Maria PC, Gal JF.
PMID: 26111259
J Phys Chem A. 2015 Jul 23;119(29):8225-36. doi: 10.1021/acs.jpca.5b04617. Epub 2015 Jul 09.

DFT calculations have been performed for a series of push-pull nitriles [(R2N)n(X═Y)iC≡N, where i = 0, 1, or 2, n = 1, 2, or 3, R2N = H2N, Me2N, or C4H8N, X = CH, N, or P, Y =...

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Raczyńska ED, Makowski M, Maria PC, et al. Can Nitriles Be Stronger Bases Than Proton Sponges in the Gas Phase? A Computational Analysis. J Phys Chem A. 2015;119(29):8225-36doi: 10.1021/acs.jpca.5b04617.
Raczyńska, E. D., Makowski, M., Maria, P. C., & Gal, J. F. (2015). Can Nitriles Be Stronger Bases Than Proton Sponges in the Gas Phase? A Computational Analysis. The journal of physical chemistry. A, 119(29), 8225-36. https://doi.org/10.1021/acs.jpca.5b04617
Raczyńska, Ewa D, et al. "Can Nitriles Be Stronger Bases Than Proton Sponges in the Gas Phase? A Computational Analysis." The journal of physical chemistry. A vol. 119,29 (2015): 8225-36. doi: https://doi.org/10.1021/acs.jpca.5b04617
Raczyńska ED, Makowski M, Maria PC, Gal JF. Can Nitriles Be Stronger Bases Than Proton Sponges in the Gas Phase? A Computational Analysis. J Phys Chem A. 2015 Jul 23;119(29):8225-36. doi: 10.1021/acs.jpca.5b04617. Epub 2015 Jul 09. PMID: 26111259.
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Spectroscopic and Computational Studies of Nitrile Hydratase: Insights into Geometric and Electronic Structure and the Mechanism of Amide Synthesis.

Chemical science

Light KM, Yamanaka Y, Odaka M, Solomon EI.
PMID: 26508996
Chem Sci. 2015 Nov 01;6(11):6280-6294. doi: 10.1039/C5SC02012C. Epub 2015 Jul 30.

Nitrile hydratases (NHases) are mononuclear nonheme enzymes that catalyze the hydration of nitriles to amides. NHase is unusual in that it utilizes a low-spin (LS) Fe

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Light KM, Yamanaka Y, Odaka M, et al. Spectroscopic and Computational Studies of Nitrile Hydratase: Insights into Geometric and Electronic Structure and the Mechanism of Amide Synthesis. Chem Sci. 2015;6(11):6280-6294doi: 10.1039/C5SC02012C.
Light, K. M., Yamanaka, Y., Odaka, M., & Solomon, E. I. (2015). Spectroscopic and Computational Studies of Nitrile Hydratase: Insights into Geometric and Electronic Structure and the Mechanism of Amide Synthesis. Chemical science, 6(11), 6280-6294. https://doi.org/10.1039/C5SC02012C
Light, Kenneth M, et al. "Spectroscopic and Computational Studies of Nitrile Hydratase: Insights into Geometric and Electronic Structure and the Mechanism of Amide Synthesis." Chemical science vol. 6,11 (2015): 6280-6294. doi: https://doi.org/10.1039/C5SC02012C
Light KM, Yamanaka Y, Odaka M, Solomon EI. Spectroscopic and Computational Studies of Nitrile Hydratase: Insights into Geometric and Electronic Structure and the Mechanism of Amide Synthesis. Chem Sci. 2015 Nov 01;6(11):6280-6294. doi: 10.1039/C5SC02012C. Epub 2015 Jul 30. PMID: 26508996; PMCID: PMC4618400.
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A photosensitizing decatungstate-based MOF as heterogeneous photocatalyst for the selective C-H alkylation of aliphatic nitriles.

Chemical communications (Cambridge, England)

Shi D, He C, Sun W, Ming Z, Meng C, Duan C.
PMID: 26954389
Chem Commun (Camb). 2016 Mar 28;52(25):4714-7. doi: 10.1039/c6cc00862c.

The efficient photosensitizing of decatungstate-based MOF with 1D channels was achieved via in situ synthesis under solvothermal conditions for light driven acceleration of β- or γ-site C-H alkylation of aliphatic nitriles. The high catalytic efficiency, excellent size selectivity, high...

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Shi D, He C, Sun W, et al. A photosensitizing decatungstate-based MOF as heterogeneous photocatalyst for the selective C-H alkylation of aliphatic nitriles. Chem Commun (Camb). 2016;52(25):4714-7doi: 10.1039/c6cc00862c.
Shi, D., He, C., Sun, W., Ming, Z., Meng, C., & Duan, C. (2016). A photosensitizing decatungstate-based MOF as heterogeneous photocatalyst for the selective C-H alkylation of aliphatic nitriles. Chemical communications (Cambridge, England), 52(25), 4714-7. https://doi.org/10.1039/c6cc00862c
Shi, Dongying, et al. "A photosensitizing decatungstate-based MOF as heterogeneous photocatalyst for the selective C-H alkylation of aliphatic nitriles." Chemical communications (Cambridge, England) vol. 52,25 (2016): 4714-7. doi: https://doi.org/10.1039/c6cc00862c
Shi D, He C, Sun W, Ming Z, Meng C, Duan C. A photosensitizing decatungstate-based MOF as heterogeneous photocatalyst for the selective C-H alkylation of aliphatic nitriles. Chem Commun (Camb). 2016 Mar 28;52(25):4714-7. doi: 10.1039/c6cc00862c. PMID: 26954389.
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Charge Effects in PCP Pincer Complexes of Ni(II) bearing Phosphinite and Imidazol(i)ophosphine Coordinating Jaws: From Synthesis to Catalysis through Bonding Analysis.

Chemistry (Weinheim an der Bergstrasse, Germany)

Vabre B, Canac Y, Lepetit C, Duhayon C, Chauvin R, Zargarian D.
PMID: 26449870
Chemistry. 2015 Nov 23;21(48):17403-14. doi: 10.1002/chem.201502491. Epub 2015 Oct 09.

This contribution reports on a new family of Ni(II) pincer complexes featuring phosphinite and functional imidazolyl arms. The proligands (R) PIMC(H) OP(R') react at room temperature with Ni(II) precursors to give the corresponding complexes [((R) PIMCOP(R') )NiBr], where (R)...

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Vabre B, Canac Y, Lepetit C, et al. Charge Effects in PCP Pincer Complexes of Ni(II) bearing Phosphinite and Imidazol(i)ophosphine Coordinating Jaws: From Synthesis to Catalysis through Bonding Analysis. Chemistry. 2015;21(48):17403-14doi: 10.1002/chem.201502491.
Vabre, B., Canac, Y., Lepetit, C., Duhayon, C., Chauvin, R., & Zargarian, D. (2015). Charge Effects in PCP Pincer Complexes of Ni(II) bearing Phosphinite and Imidazol(i)ophosphine Coordinating Jaws: From Synthesis to Catalysis through Bonding Analysis. Chemistry (Weinheim an der Bergstrasse, Germany), 21(48), 17403-14. https://doi.org/10.1002/chem.201502491
Vabre, Boris, et al. "Charge Effects in PCP Pincer Complexes of Ni(II) bearing Phosphinite and Imidazol(i)ophosphine Coordinating Jaws: From Synthesis to Catalysis through Bonding Analysis." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,48 (2015): 17403-14. doi: https://doi.org/10.1002/chem.201502491
Vabre B, Canac Y, Lepetit C, Duhayon C, Chauvin R, Zargarian D. Charge Effects in PCP Pincer Complexes of Ni(II) bearing Phosphinite and Imidazol(i)ophosphine Coordinating Jaws: From Synthesis to Catalysis through Bonding Analysis. Chemistry. 2015 Nov 23;21(48):17403-14. doi: 10.1002/chem.201502491. Epub 2015 Oct 09. PMID: 26449870.
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