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Traceless Directing-Group Strategy in the Ru-Catalyzed, Formal [3 + 3] Annulation of Anilines with Allyl Alcohols: A One-Pot, Domino Approach for the Synthesis of Quinolines.

Organic letters

Kumar GS, Kumar P, Kapur M.
PMID: 28448156
Org Lett. 2017 May 19;19(10):2494-2497. doi: 10.1021/acs.orglett.7b00715. Epub 2017 Apr 27.

A unique, ruthenium-catalyzed, [3 + 3] annulation of anilines with allyl alcohols in the synthesis of substituted quinolines is reported. The method employs a traceless directing group strategy in the proximal C-H bond activation and represents a one-pot Domino...

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Kumar GS, Kumar P, Kapur M. Traceless Directing-Group Strategy in the Ru-Catalyzed, Formal [3 + 3] Annulation of Anilines with Allyl Alcohols: A One-Pot, Domino Approach for the Synthesis of Quinolines. Org Lett. 2017;19(10):2494-2497doi: 10.1021/acs.orglett.7b00715.
Kumar, G. S., Kumar, P., & Kapur, M. (2017). Traceless Directing-Group Strategy in the Ru-Catalyzed, Formal [3 + 3] Annulation of Anilines with Allyl Alcohols: A One-Pot, Domino Approach for the Synthesis of Quinolines. Organic letters, 19(10), 2494-2497. https://doi.org/10.1021/acs.orglett.7b00715
Kumar, Gangam Srikanth, et al. "Traceless Directing-Group Strategy in the Ru-Catalyzed, Formal [3 + 3] Annulation of Anilines with Allyl Alcohols: A One-Pot, Domino Approach for the Synthesis of Quinolines." Organic letters vol. 19,10 (2017): 2494-2497. doi: https://doi.org/10.1021/acs.orglett.7b00715
Kumar GS, Kumar P, Kapur M. Traceless Directing-Group Strategy in the Ru-Catalyzed, Formal [3 + 3] Annulation of Anilines with Allyl Alcohols: A One-Pot, Domino Approach for the Synthesis of Quinolines. Org Lett. 2017 May 19;19(10):2494-2497. doi: 10.1021/acs.orglett.7b00715. Epub 2017 Apr 27. PMID: 28448156.
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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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Mutual Cooperation in the Formal Allyl Alcohol Nucleophilic Substitution and Hydration of Alkynes for the Construction of γ-Substituted Ketones.

Chemistry (Weinheim an der Bergstrasse, Germany)

Huang K, Wang H, Liu L, Chang W, Li J.
PMID: 26946315
Chemistry. 2016 May 04;22(19):6458-65. doi: 10.1002/chem.201600248. Epub 2016 Mar 22.

Mutual cooperation in the formal allyl alcohol nucleophilic substitution reaction and hydration of an alkyne has been utilized in the presence of a gold catalyst to give a series of γ-functionalized ketones with high to excellent yields. This reaction...

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Huang K, Wang H, Liu L, et al. Mutual Cooperation in the Formal Allyl Alcohol Nucleophilic Substitution and Hydration of Alkynes for the Construction of γ-Substituted Ketones. Chemistry. 2016;22(19):6458-65doi: 10.1002/chem.201600248.
Huang, K., Wang, H., Liu, L., Chang, W., & Li, J. (2016). Mutual Cooperation in the Formal Allyl Alcohol Nucleophilic Substitution and Hydration of Alkynes for the Construction of γ-Substituted Ketones. Chemistry (Weinheim an der Bergstrasse, Germany), 22(19), 6458-65. https://doi.org/10.1002/chem.201600248
Huang, Kaimeng, et al. "Mutual Cooperation in the Formal Allyl Alcohol Nucleophilic Substitution and Hydration of Alkynes for the Construction of γ-Substituted Ketones." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,19 (2016): 6458-65. doi: https://doi.org/10.1002/chem.201600248
Huang K, Wang H, Liu L, Chang W, Li J. Mutual Cooperation in the Formal Allyl Alcohol Nucleophilic Substitution and Hydration of Alkynes for the Construction of γ-Substituted Ketones. Chemistry. 2016 May 04;22(19):6458-65. doi: 10.1002/chem.201600248. Epub 2016 Mar 22. PMID: 26946315.
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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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Reactions of allyl alcohols and boronic acids with trifluoromethanesulfonyl hypervalent iodonium ylide under copper-catalysis.

Dalton transactions (Cambridge, England : 2003)

Arimori S, Takada M, Shibata N.
PMID: 26226886
Dalton Trans. 2015 Dec 07;44(45):19456-9. doi: 10.1039/c5dt02214b. Epub 2015 Jul 31.

Trifluoromethylsulfinyl and trifluoromethylthio groups are both important substituents for pharmaceuticals, agrochemicals and functional materials. We herein report the trifluoromethylthiolation of allyl alcohols 2 with trifluoromethanesulfonyl hypervalent iodonium ylide 1 under copper catalysis to provide trifluoromethylsulfinyl compounds 3. Trifluoromethylthiolation of...

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Arimori S, Takada M, Shibata N. Reactions of allyl alcohols and boronic acids with trifluoromethanesulfonyl hypervalent iodonium ylide under copper-catalysis. Dalton Trans. 2015;44(45):19456-9doi: 10.1039/c5dt02214b.
Arimori, S., Takada, M., & Shibata, N. (2015). Reactions of allyl alcohols and boronic acids with trifluoromethanesulfonyl hypervalent iodonium ylide under copper-catalysis. Dalton transactions (Cambridge, England : 2003), 44(45), 19456-9. https://doi.org/10.1039/c5dt02214b
Arimori, Sadayuki, et al. "Reactions of allyl alcohols and boronic acids with trifluoromethanesulfonyl hypervalent iodonium ylide under copper-catalysis." Dalton transactions (Cambridge, England : 2003) vol. 44,45 (2015): 19456-9. doi: https://doi.org/10.1039/c5dt02214b
Arimori S, Takada M, Shibata N. Reactions of allyl alcohols and boronic acids with trifluoromethanesulfonyl hypervalent iodonium ylide under copper-catalysis. Dalton Trans. 2015 Dec 07;44(45):19456-9. doi: 10.1039/c5dt02214b. Epub 2015 Jul 31. PMID: 26226886.
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Electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienes.

Beilstein journal of organic chemistry

Röse P, Emge S, Yoshida J, Hilt G.
PMID: 25815067
Beilstein J Org Chem. 2015 Jan 28;11:174-83. doi: 10.3762/bjoc.11.18. eCollection 2015.

The cobalt(I)-catalysed 1,4-hydrovinylation reaction of allyloxytrimethylsilane and allyl alcohol with substituted 1,3-dienes leads to hydroxy-functionalised 1,4-dienes in excellent regio- and diastereoselective fashion. Those 1,4-dienols can be converted into tetrahydrofuran and pyran derivatives under indirect electrochemical conditions generating selenium or...

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Röse P, Emge S, Yoshida J, et al. Electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienes. Beilstein J Org Chem. 2015;11:174-83doi: 10.3762/bjoc.11.18.
Röse, P., Emge, S., Yoshida, J., & Hilt, G. (2015). Electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienes. Beilstein journal of organic chemistry, 11174-83. https://doi.org/10.3762/bjoc.11.18
Röse, Philipp, et al. "Electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienes." Beilstein journal of organic chemistry vol. 11 (2015): 174-83. doi: https://doi.org/10.3762/bjoc.11.18
Röse P, Emge S, Yoshida J, Hilt G. Electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienes. Beilstein J Org Chem. 2015 Jan 28;11:174-83. doi: 10.3762/bjoc.11.18. eCollection 2015. PMID: 25815067; PMCID: PMC4361995.
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Difluoromethanesulfonyl hypervalent iodonium ylides for electrophilic difluoromethylthiolation reactions under copper catalysis.

Royal Society open science

Arimori S, Matsubara O, Takada M, Shiro M, Shibata N.
PMID: 27293790
R Soc Open Sci. 2016 May 25;3(5):160102. doi: 10.1098/rsos.160102. eCollection 2016 May.

Difluoromethanesulfonyl hypervalent iodonium ylides 2 were developed as electrophilic difluoromethylthiolation reagents for a wide range of nucleophiles. Enamines, indoles, β-keto esters, silyl enol ethers and pyrroles were effectively reacted with 2 affording desired difluoromethylthio (SCF2H)-substituted compounds in good to...

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Arimori S, Matsubara O, Takada M, et al. Difluoromethanesulfonyl hypervalent iodonium ylides for electrophilic difluoromethylthiolation reactions under copper catalysis. R Soc Open Sci. 2016;3(5):160102doi: 10.1098/rsos.160102.
Arimori, S., Matsubara, O., Takada, M., Shiro, M., & Shibata, N. (2016). Difluoromethanesulfonyl hypervalent iodonium ylides for electrophilic difluoromethylthiolation reactions under copper catalysis. Royal Society open science, 3(5), 160102. https://doi.org/10.1098/rsos.160102
Arimori, Sadayuki, et al. "Difluoromethanesulfonyl hypervalent iodonium ylides for electrophilic difluoromethylthiolation reactions under copper catalysis." Royal Society open science vol. 3,5 (2016): 160102. doi: https://doi.org/10.1098/rsos.160102
Arimori S, Matsubara O, Takada M, Shiro M, Shibata N. Difluoromethanesulfonyl hypervalent iodonium ylides for electrophilic difluoromethylthiolation reactions under copper catalysis. R Soc Open Sci. 2016 May 25;3(5):160102. doi: 10.1098/rsos.160102. eCollection 2016 May. PMID: 27293790; PMCID: PMC4892452.
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Mechanistic insights into the Pd-catalyzed direct amination of allyl alcohols: evidence for an outer-sphere mechanism involving a palladium hydride intermediate.

Chemistry (Weinheim an der Bergstrasse, Germany)

Sawadjoon S, Sjöberg PJ, Orthaber A, Matsson O, Samec JS.
PMID: 24403056
Chemistry. 2014 Feb 03;20(6):1520-4. doi: 10.1002/chem.201303431. Epub 2014 Jan 08.

The mechanism of direct amination of allyl alcohol by a palladium triphenylphosphite complex has been explored. Labelling studies show that the reaction proceeds through a π-allylpalladium intermediate. A second-order dependence of reaction rate on allyl alcohol concentration was observed....

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Sawadjoon S, Sjöberg PJ, Orthaber A, et al. Mechanistic insights into the Pd-catalyzed direct amination of allyl alcohols: evidence for an outer-sphere mechanism involving a palladium hydride intermediate. Chemistry. 2014;20(6):1520-4doi: 10.1002/chem.201303431.
Sawadjoon, S., Sjöberg, P. J., Orthaber, A., Matsson, O., & Samec, J. S. (2014). Mechanistic insights into the Pd-catalyzed direct amination of allyl alcohols: evidence for an outer-sphere mechanism involving a palladium hydride intermediate. Chemistry (Weinheim an der Bergstrasse, Germany), 20(6), 1520-4. https://doi.org/10.1002/chem.201303431
Sawadjoon, Supaporn, et al. "Mechanistic insights into the Pd-catalyzed direct amination of allyl alcohols: evidence for an outer-sphere mechanism involving a palladium hydride intermediate." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 20,6 (2014): 1520-4. doi: https://doi.org/10.1002/chem.201303431
Sawadjoon S, Sjöberg PJ, Orthaber A, Matsson O, Samec JS. Mechanistic insights into the Pd-catalyzed direct amination of allyl alcohols: evidence for an outer-sphere mechanism involving a palladium hydride intermediate. Chemistry. 2014 Feb 03;20(6):1520-4. doi: 10.1002/chem.201303431. Epub 2014 Jan 08. PMID: 24403056.
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Oxygenated Fatty Acids with Anti-rice Blast Fungus Activity in Rice Plants.

Bioscience, biotechnology, and biochemistry

Kato T, Yamaguchi Y, Namai T, Hirukawa T.
PMID: 27314783
Biosci Biotechnol Biochem. 1993 Jan;57(2):283-7. doi: 10.1271/bbb.57.283.

Expecting that the different characteristics of rice plants against rice blast fungus, that is, susceptibility of the weaker cultivar, Sasanishiki and resistance of the stronger cultivars, Fukuyuki and Fukunishiki, may be due to the absence or presence of anti-fungus...

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Kato T, Yamaguchi Y, Namai T, et al. Oxygenated Fatty Acids with Anti-rice Blast Fungus Activity in Rice Plants. Biosci Biotechnol Biochem. 1993;57(2):283-7doi: 10.1271/bbb.57.283.
Kato, T., Yamaguchi, Y., Namai, T., & Hirukawa, T. (1993). Oxygenated Fatty Acids with Anti-rice Blast Fungus Activity in Rice Plants. Bioscience, biotechnology, and biochemistry, 57(2), 283-7. https://doi.org/10.1271/bbb.57.283
Kato, T, et al. "Oxygenated Fatty Acids with Anti-rice Blast Fungus Activity in Rice Plants." Bioscience, biotechnology, and biochemistry vol. 57,2 (1993): 283-7. doi: https://doi.org/10.1271/bbb.57.283
Kato T, Yamaguchi Y, Namai T, Hirukawa T. Oxygenated Fatty Acids with Anti-rice Blast Fungus Activity in Rice Plants. Biosci Biotechnol Biochem. 1993 Jan;57(2):283-7. doi: 10.1271/bbb.57.283. PMID: 27314783.
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A General Route to β-Substituted Pyrroles by Transition-Metal Catalysis.

The Journal of organic chemistry

Bunrit A, Sawadjoon S, Tšupova S, Sjöberg PJ, Samec JS.
PMID: 26789020
J Org Chem. 2016 Feb 19;81(4):1450-60. doi: 10.1021/acs.joc.5b02581. Epub 2016 Feb 04.

An atom-efficient route to pyrroles substituted in the β-position has been achieved in four high yielding steps by a combination of Pd, Ru, and Fe catalysis with only water and ethene as side-products. The reaction is general and gives...

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Bunrit A, Sawadjoon S, Tšupova S, et al. A General Route to β-Substituted Pyrroles by Transition-Metal Catalysis. J Org Chem. 2016;81(4):1450-60doi: 10.1021/acs.joc.5b02581.
Bunrit, A., Sawadjoon, S., Tšupova, S., Sjöberg, P. J., & Samec, J. S. (2016). A General Route to β-Substituted Pyrroles by Transition-Metal Catalysis. The Journal of organic chemistry, 81(4), 1450-60. https://doi.org/10.1021/acs.joc.5b02581
Bunrit, Anon, et al. "A General Route to β-Substituted Pyrroles by Transition-Metal Catalysis." The Journal of organic chemistry vol. 81,4 (2016): 1450-60. doi: https://doi.org/10.1021/acs.joc.5b02581
Bunrit A, Sawadjoon S, Tšupova S, Sjöberg PJ, Samec JS. A General Route to β-Substituted Pyrroles by Transition-Metal Catalysis. J Org Chem. 2016 Feb 19;81(4):1450-60. doi: 10.1021/acs.joc.5b02581. Epub 2016 Feb 04. PMID: 26789020.
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First Principles Calculations for Hydrogenation of Acrolein on Pd and Pt: Chemoselectivity Depends on Steric Effects on the Surface.

Angewandte Chemie (International ed. in English)

Tuokko S, Pihko PM, Honkala K.
PMID: 26791881
Angew Chem Int Ed Engl. 2016 Jan 26;55(5):1670-4. doi: 10.1002/anie.201507631. Epub 2016 Jan 06.

The chemoselective hydrogenation of acrolein on Pt(111) and Pd(111) surfaces is investigated employing density functional theory calculations. The computed potential energy surfaces together with the analysis of reaction mechanisms demonstrate that steric effects are an important factor that governs...

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Tuokko S, Pihko PM, Honkala K. First Principles Calculations for Hydrogenation of Acrolein on Pd and Pt: Chemoselectivity Depends on Steric Effects on the Surface. Angew Chem Int Ed Engl. 2016;55(5):1670-4doi: 10.1002/anie.201507631.
Tuokko, S., Pihko, P. M., & Honkala, K. (2016). First Principles Calculations for Hydrogenation of Acrolein on Pd and Pt: Chemoselectivity Depends on Steric Effects on the Surface. Angewandte Chemie (International ed. in English), 55(5), 1670-4. https://doi.org/10.1002/anie.201507631
Tuokko, Sakari, et al. "First Principles Calculations for Hydrogenation of Acrolein on Pd and Pt: Chemoselectivity Depends on Steric Effects on the Surface." Angewandte Chemie (International ed. in English) vol. 55,5 (2016): 1670-4. doi: https://doi.org/10.1002/anie.201507631
Tuokko S, Pihko PM, Honkala K. First Principles Calculations for Hydrogenation of Acrolein on Pd and Pt: Chemoselectivity Depends on Steric Effects on the Surface. Angew Chem Int Ed Engl. 2016 Jan 26;55(5):1670-4. doi: 10.1002/anie.201507631. Epub 2016 Jan 06. PMID: 26791881.
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Strikingly simple direct alpha-allylation of aldehydes with allyl alcohols: remarkable advance in the Tsuji-Trost reaction.

Journal of the American Chemical Society

Kimura M, Horino Y, Mukai R, Tanaka S, Tamaru Y.
PMID: 11603997
J Am Chem Soc. 2001 Oct 24;123(42):10401-2. doi: 10.1021/ja011656a.

No abstract available.

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Kimura M, Horino Y, Mukai R, et al. Strikingly simple direct alpha-allylation of aldehydes with allyl alcohols: remarkable advance in the Tsuji-Trost reaction. J Am Chem Soc. 2001;123(42):10401-2doi: 10.1021/ja011656a.
Kimura, M., Horino, Y., Mukai, R., Tanaka, S., & Tamaru, Y. (2001). Strikingly simple direct alpha-allylation of aldehydes with allyl alcohols: remarkable advance in the Tsuji-Trost reaction. Journal of the American Chemical Society, 123(42), 10401-2. https://doi.org/10.1021/ja011656a
Kimura, M, et al. "Strikingly simple direct alpha-allylation of aldehydes with allyl alcohols: remarkable advance in the Tsuji-Trost reaction." Journal of the American Chemical Society vol. 123,42 (2001): 10401-2. doi: https://doi.org/10.1021/ja011656a
Kimura M, Horino Y, Mukai R, Tanaka S, Tamaru Y. Strikingly simple direct alpha-allylation of aldehydes with allyl alcohols: remarkable advance in the Tsuji-Trost reaction. J Am Chem Soc. 2001 Oct 24;123(42):10401-2. doi: 10.1021/ja011656a. PMID: 11603997.
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Showing 1 to 12 of 257 entries