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TBAI-catalyzed oxidative synthesis of benzamides from acetophenones and carbinols.

Organic & biomolecular chemistry

Sharif M, Chen J, Langer P, Beller M, Wu XF.
PMID: 25032753
Org Biomol Chem. 2014 Sep 07;12(33):6359-62. doi: 10.1039/c4ob01203h.

An interesting and convenient procedure for the oxidative transformation of acetophenones and carbinols to primary benzamides has been developed. By using tetra-n-butylammonium iodide (TBAI) as the catalyst and tert-butyl hydroperoxide (TBHP) as the oxidant, the desired benzamides were isolated...

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Sharif M, Chen J, Langer P, et al. TBAI-catalyzed oxidative synthesis of benzamides from acetophenones and carbinols. Org Biomol Chem. 2014;12(33):6359-62doi: 10.1039/c4ob01203h.
Sharif, M., Chen, J., Langer, P., Beller, M., & Wu, X. F. (2014). TBAI-catalyzed oxidative synthesis of benzamides from acetophenones and carbinols. Organic & biomolecular chemistry, 12(33), 6359-62. https://doi.org/10.1039/c4ob01203h
Sharif, Muhammad, et al. "TBAI-catalyzed oxidative synthesis of benzamides from acetophenones and carbinols." Organic & biomolecular chemistry vol. 12,33 (2014): 6359-62. doi: https://doi.org/10.1039/c4ob01203h
Sharif M, Chen J, Langer P, Beller M, Wu XF. TBAI-catalyzed oxidative synthesis of benzamides from acetophenones and carbinols. Org Biomol Chem. 2014 Sep 07;12(33):6359-62. doi: 10.1039/c4ob01203h. PMID: 25032753.
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Orbital-Overlap control in the solid-state reactivity of beta-azido-propiophenones: selective formation of cis-azo-dimers.

Organic letters

Sankaranarayanan J, Bort LN, Mandel SM, Chen P, Krause JA, Brooks EE, Tsang P, Gudmundsdottir AD.
PMID: 18254638
Org Lett. 2008 Mar 06;10(5):937-40. doi: 10.1021/ol703098q. Epub 2008 Feb 07.

Solid-state photolysis of 1a,b yields selectively cis-3a,b. X-ray analysis of 1a,b reveals the molecules adopt an extended structure and as such the crystal packing arrangement consists of planar, pi-stacked molecules. The shortest intermolecular distance between adjacent N-atoms is approximately...

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Sankaranarayanan J, Bort LN, Mandel SM, et al. Orbital-Overlap control in the solid-state reactivity of beta-azido-propiophenones: selective formation of cis-azo-dimers. Org Lett. 2008;10(5):937-40doi: 10.1021/ol703098q.
Sankaranarayanan, J., Bort, L. N., Mandel, S. M., Chen, P., Krause, J. A., Brooks, E. E., Tsang, P., & Gudmundsdottir, A. D. (2008). Orbital-Overlap control in the solid-state reactivity of beta-azido-propiophenones: selective formation of cis-azo-dimers. Organic letters, 10(5), 937-40. https://doi.org/10.1021/ol703098q
Sankaranarayanan, Jagadis, et al. "Orbital-Overlap control in the solid-state reactivity of beta-azido-propiophenones: selective formation of cis-azo-dimers." Organic letters vol. 10,5 (2008): 937-40. doi: https://doi.org/10.1021/ol703098q
Sankaranarayanan J, Bort LN, Mandel SM, Chen P, Krause JA, Brooks EE, Tsang P, Gudmundsdottir AD. Orbital-Overlap control in the solid-state reactivity of beta-azido-propiophenones: selective formation of cis-azo-dimers. Org Lett. 2008 Mar 06;10(5):937-40. doi: 10.1021/ol703098q. Epub 2008 Feb 07. PMID: 18254638.
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Influences of electronic effects and anions on the enantioselectivity in the oxazaborolidine-catalyzed asymmetric borane reduction of ketones.

The Journal of organic chemistry

Xu J, Wei T, Zhang Q.
PMID: 15387612
J Org Chem. 2004 Oct 01;69(20):6860-6. doi: 10.1021/jo048959i.

The influence of electronic effects on the enantioselectivity of the oxazaborolidine-catalyzed asymmetric borane reduction of ketones has been observed and investigated with use of para-substituted acetophenones and propiophenones with a variety of functional groups and B-unsubstituted and B-methoxyoxazaborolidines derived...

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Xu J, Wei T, Zhang Q. Influences of electronic effects and anions on the enantioselectivity in the oxazaborolidine-catalyzed asymmetric borane reduction of ketones. J Org Chem. 2004;69(20):6860-6doi: 10.1021/jo048959i.
Xu, J., Wei, T., & Zhang, Q. (2004). Influences of electronic effects and anions on the enantioselectivity in the oxazaborolidine-catalyzed asymmetric borane reduction of ketones. The Journal of organic chemistry, 69(20), 6860-6. https://doi.org/10.1021/jo048959i
Xu, Jiaxi, et al. "Influences of electronic effects and anions on the enantioselectivity in the oxazaborolidine-catalyzed asymmetric borane reduction of ketones." The Journal of organic chemistry vol. 69,20 (2004): 6860-6. doi: https://doi.org/10.1021/jo048959i
Xu J, Wei T, Zhang Q. Influences of electronic effects and anions on the enantioselectivity in the oxazaborolidine-catalyzed asymmetric borane reduction of ketones. J Org Chem. 2004 Oct 01;69(20):6860-6. doi: 10.1021/jo048959i. PMID: 15387612.
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Copper/Palladium Bimetallic System for the Synthesis of Isobenzofuranones through [4 + 1] Annulation between Propiophenones and Benzoic Acids.

Organic letters

Liang X, Xiong M, Zhu H, Shi K, Zhou Y, Pan Y.
PMID: 33284633
Org Lett. 2020 Dec 18;22(24):9568-9573. doi: 10.1021/acs.orglett.0c03627. Epub 2020 Dec 07.

A copper/palladium-catalyzed annulation from benzoic acids and propiophenones for the synthesis of isobenzofuranones was reported. The Cu-(2,2,6,6-tetramethylpiperidin-1-yl)oxyl system showed a great ability to activate the C-H bond on the α- and β-carbons of a carbonyl group, and the in...

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Liang X, Xiong M, Zhu H, et al. Copper/Palladium Bimetallic System for the Synthesis of Isobenzofuranones through [4 + 1] Annulation between Propiophenones and Benzoic Acids. Org Lett. 2020;22(24):9568-9573doi: 10.1021/acs.orglett.0c03627.
Liang, X., Xiong, M., Zhu, H., Shi, K., Zhou, Y., & Pan, Y. (2020). Copper/Palladium Bimetallic System for the Synthesis of Isobenzofuranones through [4 + 1] Annulation between Propiophenones and Benzoic Acids. Organic letters, 22(24), 9568-9573. https://doi.org/10.1021/acs.orglett.0c03627
Liang, Xiao, et al. "Copper/Palladium Bimetallic System for the Synthesis of Isobenzofuranones through [4 + 1] Annulation between Propiophenones and Benzoic Acids." Organic letters vol. 22,24 (2020): 9568-9573. doi: https://doi.org/10.1021/acs.orglett.0c03627
Liang X, Xiong M, Zhu H, Shi K, Zhou Y, Pan Y. Copper/Palladium Bimetallic System for the Synthesis of Isobenzofuranones through [4 + 1] Annulation between Propiophenones and Benzoic Acids. Org Lett. 2020 Dec 18;22(24):9568-9573. doi: 10.1021/acs.orglett.0c03627. Epub 2020 Dec 07. PMID: 33284633.
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Metal-Free Oxidative Nitration of α-Carbon of Carbonyls Leads to One-Pot Synthesis of Thiohydroximic Acids from Acetophenones.

Organic letters

Dighe SU, Mukhopadhyay S, Priyanka K, Batra S.
PMID: 27541178
Org Lett. 2016 Sep 02;18(17):4190-3. doi: 10.1021/acs.orglett.6b01807. Epub 2016 Aug 19.

A metal-free nitration of the α-C-H to carbonyl in propiophenones was achieved with I2/NaNO2 in the presence of an oxidant in dimethyl sulfoxide (DMSO) as the medium. Conversely under similar conditions, reaction of acetophenones produced thiohydroximic acids via a...

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Dighe SU, Mukhopadhyay S, Priyanka K, et al. Metal-Free Oxidative Nitration of α-Carbon of Carbonyls Leads to One-Pot Synthesis of Thiohydroximic Acids from Acetophenones. Org Lett. 2016;18(17):4190-3doi: 10.1021/acs.orglett.6b01807.
Dighe, S. U., Mukhopadhyay, S., Priyanka, K., & Batra, S. (2016). Metal-Free Oxidative Nitration of α-Carbon of Carbonyls Leads to One-Pot Synthesis of Thiohydroximic Acids from Acetophenones. Organic letters, 18(17), 4190-3. https://doi.org/10.1021/acs.orglett.6b01807
Dighe, Shashikant U, et al. "Metal-Free Oxidative Nitration of α-Carbon of Carbonyls Leads to One-Pot Synthesis of Thiohydroximic Acids from Acetophenones." Organic letters vol. 18,17 (2016): 4190-3. doi: https://doi.org/10.1021/acs.orglett.6b01807
Dighe SU, Mukhopadhyay S, Priyanka K, Batra S. Metal-Free Oxidative Nitration of α-Carbon of Carbonyls Leads to One-Pot Synthesis of Thiohydroximic Acids from Acetophenones. Org Lett. 2016 Sep 02;18(17):4190-3. doi: 10.1021/acs.orglett.6b01807. Epub 2016 Aug 19. PMID: 27541178.
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Benzimidazoles from Aryl Alkyl Ketones and 2-Amino Anilines by an Iodine Catalyzed Oxidative C(CO)-C(alkyl) Bond Cleavage.

The Journal of organic chemistry

Ravi O, Shaikh A, Upare A, Singarapu KK, Bathula SR.
PMID: 28378580
J Org Chem. 2017 Apr 21;82(8):4422-4428. doi: 10.1021/acs.joc.7b00165. Epub 2017 Apr 10.

Novel molecular iodine catalyzed cyclization reactions of 2-amino anilines with aryl alkyl ketones under oxidant and metal-free conditions are described. The reaction likely involves sequential C-N bond formation followed by C(CO)-C(alkyl) bond cleavage. Various 2-substituted benzimidazoles are obtained in...

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Ravi O, Shaikh A, Upare A, et al. Benzimidazoles from Aryl Alkyl Ketones and 2-Amino Anilines by an Iodine Catalyzed Oxidative C(CO)-C(alkyl) Bond Cleavage. J Org Chem. 2017;82(8):4422-4428doi: 10.1021/acs.joc.7b00165.
Ravi, O., Shaikh, A., Upare, A., Singarapu, K. K., & Bathula, S. R. (2017). Benzimidazoles from Aryl Alkyl Ketones and 2-Amino Anilines by an Iodine Catalyzed Oxidative C(CO)-C(alkyl) Bond Cleavage. The Journal of organic chemistry, 82(8), 4422-4428. https://doi.org/10.1021/acs.joc.7b00165
Ravi, Owk, et al. "Benzimidazoles from Aryl Alkyl Ketones and 2-Amino Anilines by an Iodine Catalyzed Oxidative C(CO)-C(alkyl) Bond Cleavage." The Journal of organic chemistry vol. 82,8 (2017): 4422-4428. doi: https://doi.org/10.1021/acs.joc.7b00165
Ravi O, Shaikh A, Upare A, Singarapu KK, Bathula SR. Benzimidazoles from Aryl Alkyl Ketones and 2-Amino Anilines by an Iodine Catalyzed Oxidative C(CO)-C(alkyl) Bond Cleavage. J Org Chem. 2017 Apr 21;82(8):4422-4428. doi: 10.1021/acs.joc.7b00165. Epub 2017 Apr 10. PMID: 28378580.
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Pd-catalyzed cross-coupling of aryl carboxylic acids with propiophenones through a combination of decarboxylation and dehydrogenation.

Chemistry (Weinheim an der Bergstrasse, Germany)

Zhou J, Wu G, Zhang M, Jie X, Su W.
PMID: 22653576
Chemistry. 2012 Jun 25;18(26):8032-6. doi: 10.1002/chem.201200829. Epub 2012 May 31.

A Heck of a reaction: With a PCy(3)-supported Pd catalyst, aryl carboxylic acids cross-couple to saturated propiophenones through a combination of decarboxylation and dehydrogenation to give chalcones bearing a variety of functional groups in generally good yields (see scheme)....

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Zhou J, Wu G, Zhang M, et al. Pd-catalyzed cross-coupling of aryl carboxylic acids with propiophenones through a combination of decarboxylation and dehydrogenation. Chemistry. 2012;18(26):8032-6doi: 10.1002/chem.201200829.
Zhou, J., Wu, G., Zhang, M., Jie, X., & Su, W. (2012). Pd-catalyzed cross-coupling of aryl carboxylic acids with propiophenones through a combination of decarboxylation and dehydrogenation. Chemistry (Weinheim an der Bergstrasse, Germany), 18(26), 8032-6. https://doi.org/10.1002/chem.201200829
Zhou, Jun, et al. "Pd-catalyzed cross-coupling of aryl carboxylic acids with propiophenones through a combination of decarboxylation and dehydrogenation." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 18,26 (2012): 8032-6. doi: https://doi.org/10.1002/chem.201200829
Zhou J, Wu G, Zhang M, Jie X, Su W. Pd-catalyzed cross-coupling of aryl carboxylic acids with propiophenones through a combination of decarboxylation and dehydrogenation. Chemistry. 2012 Jun 25;18(26):8032-6. doi: 10.1002/chem.201200829. Epub 2012 May 31. PMID: 22653576.
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Synthesis of β,β-diaryl propiophenones via palladium-catalyzed domino arylboronation, elimination and enone hydroarylation of enaminones.

Organic & biomolecular chemistry

Zhong S, Lu Y, Zhang Y, Liu Y, Wan JP.
PMID: 27271030
Org Biomol Chem. 2016 Jul 14;14(26):6270-3. doi: 10.1039/c6ob01038e. Epub 2016 Jun 06.

The syntheses of β,β-diaryl aryl propiophenones have been realized via palladium-catalyzed domino reactions of dimethyl amino functionalized enaminones and aryl boronic acids. This is the first example of transition metal-catalyzed enaminone C-N bond conversion for the generation of a...

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Zhong S, Lu Y, Zhang Y, et al. Synthesis of β,β-diaryl propiophenones via palladium-catalyzed domino arylboronation, elimination and enone hydroarylation of enaminones. Org Biomol Chem. 2016;14(26):6270-3doi: 10.1039/c6ob01038e.
Zhong, S., Lu, Y., Zhang, Y., Liu, Y., & Wan, J. P. (2016). Synthesis of β,β-diaryl propiophenones via palladium-catalyzed domino arylboronation, elimination and enone hydroarylation of enaminones. Organic & biomolecular chemistry, 14(26), 6270-3. https://doi.org/10.1039/c6ob01038e
Zhong, Shanshan, et al. "Synthesis of β,β-diaryl propiophenones via palladium-catalyzed domino arylboronation, elimination and enone hydroarylation of enaminones." Organic & biomolecular chemistry vol. 14,26 (2016): 6270-3. doi: https://doi.org/10.1039/c6ob01038e
Zhong S, Lu Y, Zhang Y, Liu Y, Wan JP. Synthesis of β,β-diaryl propiophenones via palladium-catalyzed domino arylboronation, elimination and enone hydroarylation of enaminones. Org Biomol Chem. 2016 Jul 14;14(26):6270-3. doi: 10.1039/c6ob01038e. Epub 2016 Jun 06. PMID: 27271030.
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Copper-catalyzed direct α-ketoesterification of propiophenones with acetophenones via C(sp(3))-H oxidative cross-coupling.

Chemical communications (Cambridge, England)

Du J, Zhang X, Sun X, Wang L.
PMID: 25669419
Chem Commun (Camb). 2015 Mar 14;51(21):4372-5. doi: 10.1039/c4cc09524c.

A novel copper-catalyzed direct α-ketoesterification of propiophenones with acetophenones via C(sp(3))-H oxidative cross-coupling was developed. The reaction utilized O2 as a clean oxidant with high atom economy and the starting materials are facile and commercially available.

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Du J, Zhang X, Sun X, et al. Copper-catalyzed direct α-ketoesterification of propiophenones with acetophenones via C(sp(3))-H oxidative cross-coupling. Chem Commun (Camb). 2015;51(21):4372-5doi: 10.1039/c4cc09524c.
Du, J., Zhang, X., Sun, X., & Wang, L. (2015). Copper-catalyzed direct α-ketoesterification of propiophenones with acetophenones via C(sp(3))-H oxidative cross-coupling. Chemical communications (Cambridge, England), 51(21), 4372-5. https://doi.org/10.1039/c4cc09524c
Du, Juan, et al. "Copper-catalyzed direct α-ketoesterification of propiophenones with acetophenones via C(sp(3))-H oxidative cross-coupling." Chemical communications (Cambridge, England) vol. 51,21 (2015): 4372-5. doi: https://doi.org/10.1039/c4cc09524c
Du J, Zhang X, Sun X, Wang L. Copper-catalyzed direct α-ketoesterification of propiophenones with acetophenones via C(sp(3))-H oxidative cross-coupling. Chem Commun (Camb). 2015 Mar 14;51(21):4372-5. doi: 10.1039/c4cc09524c. PMID: 25669419.
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Relative Rate Profiles of Functionalized Iodoarene Catalysts for Iodine(III) Oxidations.

The Journal of organic chemistry

Lex TR, Swasy MI, Whitehead DC.
PMID: 26599392
J Org Chem. 2015 Dec 18;80(24):12234-43. doi: 10.1021/acs.joc.5b02129. Epub 2015 Dec 07.

A series of rate studies were conducted to evaluate the steric and electronic properties that govern the reactivity of iodoarene amide catalysts in the α-oxytosylation of propiophenone. A meta-substituted benzamide catalyst emerged as the most reactive. This catalyst was...

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Lex TR, Swasy MI, Whitehead DC. Relative Rate Profiles of Functionalized Iodoarene Catalysts for Iodine(III) Oxidations. J Org Chem. 2015;80(24):12234-43doi: 10.1021/acs.joc.5b02129.
Lex, T. R., Swasy, M. I., & Whitehead, D. C. (2015). Relative Rate Profiles of Functionalized Iodoarene Catalysts for Iodine(III) Oxidations. The Journal of organic chemistry, 80(24), 12234-43. https://doi.org/10.1021/acs.joc.5b02129
Lex, Timothy R, et al. "Relative Rate Profiles of Functionalized Iodoarene Catalysts for Iodine(III) Oxidations." The Journal of organic chemistry vol. 80,24 (2015): 12234-43. doi: https://doi.org/10.1021/acs.joc.5b02129
Lex TR, Swasy MI, Whitehead DC. Relative Rate Profiles of Functionalized Iodoarene Catalysts for Iodine(III) Oxidations. J Org Chem. 2015 Dec 18;80(24):12234-43. doi: 10.1021/acs.joc.5b02129. Epub 2015 Dec 07. PMID: 26599392.
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Showing 1 to 10 of 10 entries