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Ruthenium-Catalyzed Peri- and Ortho-Alkynylation with Bromoalkynes via Insertion and Elimination.

Organic letters

Tan E, Konovalov AI, Fernández GA, Dorel R, Echavarren AM.
PMID: 28976200
Org Lett. 2017 Oct 20;19(20):5561-5564. doi: 10.1021/acs.orglett.7b02655. Epub 2017 Oct 04.

The alkynylation of naphthols takes place with total regiocontrol at the peri position of the hydroxyl group in the presence of [RuCl

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Tan E, Konovalov AI, Fernández GA, et al. Ruthenium-Catalyzed Peri- and Ortho-Alkynylation with Bromoalkynes via Insertion and Elimination. Org Lett. 2017;19(20):5561-5564doi: 10.1021/acs.orglett.7b02655.
Tan, E., Konovalov, A. I., Fernández, G. A., Dorel, R., & Echavarren, A. M. (2017). Ruthenium-Catalyzed Peri- and Ortho-Alkynylation with Bromoalkynes via Insertion and Elimination. Organic letters, 19(20), 5561-5564. https://doi.org/10.1021/acs.orglett.7b02655
Tan, Eric, et al. "Ruthenium-Catalyzed Peri- and Ortho-Alkynylation with Bromoalkynes via Insertion and Elimination." Organic letters vol. 19,20 (2017): 5561-5564. doi: https://doi.org/10.1021/acs.orglett.7b02655
Tan E, Konovalov AI, Fernández GA, Dorel R, Echavarren AM. Ruthenium-Catalyzed Peri- and Ortho-Alkynylation with Bromoalkynes via Insertion and Elimination. Org Lett. 2017 Oct 20;19(20):5561-5564. doi: 10.1021/acs.orglett.7b02655. Epub 2017 Oct 04. PMID: 28976200; PMCID: PMC5679662.
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Correction: Phosphine-catalyzed Friedel-Crafts reaction of naphthols with para-quinone methides: expedient access to triarylmethanes.

Organic & biomolecular chemistry

Zhou T, Li S, Huang B, Li C, Zhao Y, Chen J, Chen A, Xiao Y, Liu L, Zhang J.
PMID: 28548151
Org Biomol Chem. 2017 Jun 14;15(23):5097. doi: 10.1039/c7ob90087b.

Correction for 'Phosphine-catalyzed Friedel-Crafts reaction of naphthols with para-quinone methides: expedient access to triarylmethanes' by Tao Zhou et al., Org. Biomol. Chem., 2017, DOI: 10.1039/c7ob00911a.

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Zhou T, Li S, Huang B, et al. Correction: Phosphine-catalyzed Friedel-Crafts reaction of naphthols with para-quinone methides: expedient access to triarylmethanes. Org Biomol Chem. 2017;15(23):5097doi: 10.1039/c7ob90087b.
Zhou, T., Li, S., Huang, B., Li, C., Zhao, Y., Chen, J., Chen, A., Xiao, Y., Liu, L., & Zhang, J. (2017). Correction: Phosphine-catalyzed Friedel-Crafts reaction of naphthols with para-quinone methides: expedient access to triarylmethanes. Organic & biomolecular chemistry, 15(23), 5097. https://doi.org/10.1039/c7ob90087b
Zhou, Tao, et al. "Correction: Phosphine-catalyzed Friedel-Crafts reaction of naphthols with para-quinone methides: expedient access to triarylmethanes." Organic & biomolecular chemistry vol. 15,23 (2017): 5097. doi: https://doi.org/10.1039/c7ob90087b
Zhou T, Li S, Huang B, Li C, Zhao Y, Chen J, Chen A, Xiao Y, Liu L, Zhang J. Correction: Phosphine-catalyzed Friedel-Crafts reaction of naphthols with para-quinone methides: expedient access to triarylmethanes. Org Biomol Chem. 2017 Jun 14;15(23):5097. doi: 10.1039/c7ob90087b. PMID: 28548151.
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Asymmetric Dearomatization of β-Naphthols through a Bifunctional-Thiourea-Catalyzed Michael Reaction.

Angewandte Chemie (International ed. in English)

Wang SG, Liu XJ, Zhao QC, Zheng C, Wang SB, You SL.
PMID: 26463712
Angew Chem Int Ed Engl. 2015 Dec 01;54(49):14929-32. doi: 10.1002/anie.201507998. Epub 2015 Oct 14.

An intermolecular asymmetric dearomatization reaction of β-naphthols with nitroethylene through a chiral-thiourea-catalyzed Michael reaction is described. Enantioenriched functionalized β-naphthalenones with an all-carbon quaternary stereogenic center could thus be easily constructed from simple naphthol derivatives in good yields and excellent...

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Wang SG, Liu XJ, Zhao QC, et al. Asymmetric Dearomatization of β-Naphthols through a Bifunctional-Thiourea-Catalyzed Michael Reaction. Angew Chem Int Ed Engl. 2015;54(49):14929-32doi: 10.1002/anie.201507998.
Wang, S. G., Liu, X. J., Zhao, Q. C., Zheng, C., Wang, S. B., & You, S. L. (2015). Asymmetric Dearomatization of β-Naphthols through a Bifunctional-Thiourea-Catalyzed Michael Reaction. Angewandte Chemie (International ed. in English), 54(49), 14929-32. https://doi.org/10.1002/anie.201507998
Wang, Shou-Guo, et al. "Asymmetric Dearomatization of β-Naphthols through a Bifunctional-Thiourea-Catalyzed Michael Reaction." Angewandte Chemie (International ed. in English) vol. 54,49 (2015): 14929-32. doi: https://doi.org/10.1002/anie.201507998
Wang SG, Liu XJ, Zhao QC, Zheng C, Wang SB, You SL. Asymmetric Dearomatization of β-Naphthols through a Bifunctional-Thiourea-Catalyzed Michael Reaction. Angew Chem Int Ed Engl. 2015 Dec 01;54(49):14929-32. doi: 10.1002/anie.201507998. Epub 2015 Oct 14. PMID: 26463712.
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Synthesis of spiroindanes by palladium-catalyzed oxidative annulation of non- or weakly activated 1,3-dienes involving C-H functionalization.

Chemical communications (Cambridge, England)

Khan I, Chidipudi SR, Lam HW.
PMID: 25571940
Chem Commun (Camb). 2015 Feb 14;51(13):2613-6. doi: 10.1039/c4cc09496d.

The synthesis of spiroindanes by the palladium-catalyzed oxidative annulation of non- or weakly activated 1,3-dienes with 2-aryl cyclic 1,3-dicarbonyl compounds is described. Examples of the dearomatizing oxidative annulation of 1,3-dienes with 1-aryl-2-naphthols are also presented.

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Khan I, Chidipudi SR, Lam HW. Synthesis of spiroindanes by palladium-catalyzed oxidative annulation of non- or weakly activated 1,3-dienes involving C-H functionalization. Chem Commun (Camb). 2015;51(13):2613-6doi: 10.1039/c4cc09496d.
Khan, I., Chidipudi, S. R., & Lam, H. W. (2015). Synthesis of spiroindanes by palladium-catalyzed oxidative annulation of non- or weakly activated 1,3-dienes involving C-H functionalization. Chemical communications (Cambridge, England), 51(13), 2613-6. https://doi.org/10.1039/c4cc09496d
Khan, Imtiaz, et al. "Synthesis of spiroindanes by palladium-catalyzed oxidative annulation of non- or weakly activated 1,3-dienes involving C-H functionalization." Chemical communications (Cambridge, England) vol. 51,13 (2015): 2613-6. doi: https://doi.org/10.1039/c4cc09496d
Khan I, Chidipudi SR, Lam HW. Synthesis of spiroindanes by palladium-catalyzed oxidative annulation of non- or weakly activated 1,3-dienes involving C-H functionalization. Chem Commun (Camb). 2015 Feb 14;51(13):2613-6. doi: 10.1039/c4cc09496d. PMID: 25571940.
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Transition-metal-catalyzed asymmetric allylic dearomatization reactions.

Accounts of chemical research

Zhuo CX, Zheng C, You SL.
PMID: 24940612
Acc Chem Res. 2014 Aug 19;47(8):2558-73. doi: 10.1021/ar500167f. Epub 2014 Jun 18.

Dearomatization reactions serve as powerful methods for the synthesis of highly functionalized, three-dimensional structures starting with simple planar aromatic compounds. Among processes of this type, catalytic asymmetric dearomatization (CADA) reactions are attractive owing to the large number of aromatic...

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Zhuo CX, Zheng C, You SL. Transition-metal-catalyzed asymmetric allylic dearomatization reactions. Acc Chem Res. 2014;47(8):2558-73doi: 10.1021/ar500167f.
Zhuo, C. X., Zheng, C., & You, S. L. (2014). Transition-metal-catalyzed asymmetric allylic dearomatization reactions. Accounts of chemical research, 47(8), 2558-73. https://doi.org/10.1021/ar500167f
Zhuo, Chun-Xiang, et al. "Transition-metal-catalyzed asymmetric allylic dearomatization reactions." Accounts of chemical research vol. 47,8 (2014): 2558-73. doi: https://doi.org/10.1021/ar500167f
Zhuo CX, Zheng C, You SL. Transition-metal-catalyzed asymmetric allylic dearomatization reactions. Acc Chem Res. 2014 Aug 19;47(8):2558-73. doi: 10.1021/ar500167f. Epub 2014 Jun 18. PMID: 24940612.
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Mg(II) -Mediated Catalytic Asymmetric Dearomatization (CADA) Reaction of β-Naphthols with Dialkyl Acetylenedicarboxylates.

Chemistry (Weinheim an der Bergstrasse, Germany)

Wang L, Yang D, Li D, Wang P, Wang K, Wang J, Jiang X, Wang R.
PMID: 27139904
Chemistry. 2016 Jun 13;22(25):8483-7. doi: 10.1002/chem.201601399. Epub 2016 May 03.

A Mg(II) -mediated catalytic asymmetric dearomatization (CADA) reaction of β-naphthols has been developed. The reaction proceeds under ambient temperature and give a series of chiral trisubstituted olefins with good chemoselectivities, Z/E ratios, and excellent enantioselectivities. A fluorinated β-naphthol was...

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Wang L, Yang D, Li D, et al. Mg(II) -Mediated Catalytic Asymmetric Dearomatization (CADA) Reaction of β-Naphthols with Dialkyl Acetylenedicarboxylates. Chemistry. 2016;22(25):8483-7doi: 10.1002/chem.201601399.
Wang, L., Yang, D., Li, D., Wang, P., Wang, K., Wang, J., Jiang, X., & Wang, R. (2016). Mg(II) -Mediated Catalytic Asymmetric Dearomatization (CADA) Reaction of β-Naphthols with Dialkyl Acetylenedicarboxylates. Chemistry (Weinheim an der Bergstrasse, Germany), 22(25), 8483-7. https://doi.org/10.1002/chem.201601399
Wang, Linqing, et al. "Mg(II) -Mediated Catalytic Asymmetric Dearomatization (CADA) Reaction of β-Naphthols with Dialkyl Acetylenedicarboxylates." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,25 (2016): 8483-7. doi: https://doi.org/10.1002/chem.201601399
Wang L, Yang D, Li D, Wang P, Wang K, Wang J, Jiang X, Wang R. Mg(II) -Mediated Catalytic Asymmetric Dearomatization (CADA) Reaction of β-Naphthols with Dialkyl Acetylenedicarboxylates. Chemistry. 2016 Jun 13;22(25):8483-7. doi: 10.1002/chem.201601399. Epub 2016 May 03. PMID: 27139904.
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Transfer of Chirality in the Rhodium-Catalyzed Chemoselective and Regioselective Allylic Alkylation of Hydroxyarenes with Vinyl Aziridines.

Organic letters

Lin TY, Wu HH, Feng JJ, Zhang J.
PMID: 28530815
Org Lett. 2017 Jun 02;19(11):2897-2900. doi: 10.1021/acs.orglett.7b01136. Epub 2017 May 22.

By taking advantage of chirality-transfer strategy, a chemo- and regioselective allylic alkylation of naphthols and phenols with vinylaziridines provides an atom-economic and efficient method for the synthesis of enantioenriched 2-vinyl-2-arylethylamine derivatives. Use of readily available starting materials, a broad...

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Lin TY, Wu HH, Feng JJ, et al. Transfer of Chirality in the Rhodium-Catalyzed Chemoselective and Regioselective Allylic Alkylation of Hydroxyarenes with Vinyl Aziridines. Org Lett. 2017;19(11):2897-2900doi: 10.1021/acs.orglett.7b01136.
Lin, T. Y., Wu, H. H., Feng, J. J., & Zhang, J. (2017). Transfer of Chirality in the Rhodium-Catalyzed Chemoselective and Regioselective Allylic Alkylation of Hydroxyarenes with Vinyl Aziridines. Organic letters, 19(11), 2897-2900. https://doi.org/10.1021/acs.orglett.7b01136
Lin, Tao-Yan, et al. "Transfer of Chirality in the Rhodium-Catalyzed Chemoselective and Regioselective Allylic Alkylation of Hydroxyarenes with Vinyl Aziridines." Organic letters vol. 19,11 (2017): 2897-2900. doi: https://doi.org/10.1021/acs.orglett.7b01136
Lin TY, Wu HH, Feng JJ, Zhang J. Transfer of Chirality in the Rhodium-Catalyzed Chemoselective and Regioselective Allylic Alkylation of Hydroxyarenes with Vinyl Aziridines. Org Lett. 2017 Jun 02;19(11):2897-2900. doi: 10.1021/acs.orglett.7b01136. Epub 2017 May 22. PMID: 28530815.
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Chiral N,N'-Dioxide-Scandium(III)-Catalyzed Asymmetric Dearomatization of 2-Naphthols through an Amination Reaction.

Chemistry (Weinheim an der Bergstrasse, Germany)

Lian X, Lin L, Wang G, Liu X, Feng X.
PMID: 26449515
Chemistry. 2015 Nov 23;21(48):17453-8. doi: 10.1002/chem.201503276. Epub 2015 Oct 09.

A catalytic asymmetric dearomatization of 2-naphthols with azodicarboxylates has been accomplished by using a N,N'-dioxide-scandium(III) complex as a chiral catalyst. A number of optically active β-naphthalenone compounds with a nitrogen-containing quaternary carbon stereocenter were obtained in up to 99...

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Lian X, Lin L, Wang G, et al. Chiral N,N'-Dioxide-Scandium(III)-Catalyzed Asymmetric Dearomatization of 2-Naphthols through an Amination Reaction. Chemistry. 2015;21(48):17453-8doi: 10.1002/chem.201503276.
Lian, X., Lin, L., Wang, G., Liu, X., & Feng, X. (2015). Chiral N,N'-Dioxide-Scandium(III)-Catalyzed Asymmetric Dearomatization of 2-Naphthols through an Amination Reaction. Chemistry (Weinheim an der Bergstrasse, Germany), 21(48), 17453-8. https://doi.org/10.1002/chem.201503276
Lian, Xiangjin, et al. "Chiral N,N'-Dioxide-Scandium(III)-Catalyzed Asymmetric Dearomatization of 2-Naphthols through an Amination Reaction." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,48 (2015): 17453-8. doi: https://doi.org/10.1002/chem.201503276
Lian X, Lin L, Wang G, Liu X, Feng X. Chiral N,N'-Dioxide-Scandium(III)-Catalyzed Asymmetric Dearomatization of 2-Naphthols through an Amination Reaction. Chemistry. 2015 Nov 23;21(48):17453-8. doi: 10.1002/chem.201503276. Epub 2015 Oct 09. PMID: 26449515.
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Tandem Esterification/1,4-Addition-Type Friedel-Crafts Alkylation Reactions of Phenols/Naphthols with Olefinic Thioazlactones: Access to Functionalized 1,2-Dihydrobenzo[f]chromen-3-ones and 3,4-Dihydrochromen-2-ones.

The Journal of organic chemistry

Ziyaei Halimehjani A, Khoshdoun M.
PMID: 27310869
J Org Chem. 2016 Jul 01;81(13):5699-704. doi: 10.1021/acs.joc.6b00740. Epub 2016 Jun 23.

An efficient approach for the synthesis of novel alkyl 2,3-dihydro-3-oxo-1-aryl-1H-benzo[f]chromen-2-ylcarbamodithioates and alkyl 3,4-dihydro-2-oxo-4-aryl-2H-chromen-3-ylcarbamodithioates from 2-(alkylthio)thioazlactones (thioazlactones) and phenols or naphthols catalyzed by PTSA was developed. The reaction proceeds via a domino esterification/intramolecular 1,4-addition-type Friedel-Crafts alkylation reaction to afford interesting...

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Ziyaei Halimehjani A, Khoshdoun M. Tandem Esterification/1,4-Addition-Type Friedel-Crafts Alkylation Reactions of Phenols/Naphthols with Olefinic Thioazlactones: Access to Functionalized 1,2-Dihydrobenzo[f]chromen-3-ones and 3,4-Dihydrochromen-2-ones. J Org Chem. 2016;81(13):5699-704doi: 10.1021/acs.joc.6b00740.
Ziyaei Halimehjani, A., & Khoshdoun, M. (2016). Tandem Esterification/1,4-Addition-Type Friedel-Crafts Alkylation Reactions of Phenols/Naphthols with Olefinic Thioazlactones: Access to Functionalized 1,2-Dihydrobenzo[f]chromen-3-ones and 3,4-Dihydrochromen-2-ones. The Journal of organic chemistry, 81(13), 5699-704. https://doi.org/10.1021/acs.joc.6b00740
Ziyaei Halimehjani, Azim, and Khoshdoun, Maryam. "Tandem Esterification/1,4-Addition-Type Friedel-Crafts Alkylation Reactions of Phenols/Naphthols with Olefinic Thioazlactones: Access to Functionalized 1,2-Dihydrobenzo[f]chromen-3-ones and 3,4-Dihydrochromen-2-ones." The Journal of organic chemistry vol. 81,13 (2016): 5699-704. doi: https://doi.org/10.1021/acs.joc.6b00740
Ziyaei Halimehjani A, Khoshdoun M. Tandem Esterification/1,4-Addition-Type Friedel-Crafts Alkylation Reactions of Phenols/Naphthols with Olefinic Thioazlactones: Access to Functionalized 1,2-Dihydrobenzo[f]chromen-3-ones and 3,4-Dihydrochromen-2-ones. J Org Chem. 2016 Jul 01;81(13):5699-704. doi: 10.1021/acs.joc.6b00740. Epub 2016 Jun 23. PMID: 27310869.
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Air Oxidation of 2-Aryl-1-tetralones in Basic, Neutral, and Acidic Media: An Unprecedented Oxidative Aryl Migration to 2-Aryloxy-1-naphthols under Acidic Condition.

The Journal of organic chemistry

Ishikawa T, Hino K, Yoneda T, Murota M, Yamaguchi K, Watanabe T.
PMID: 11674642
J Org Chem. 1999 Jul 23;64(15):5691-5695. doi: 10.1021/jo9824854.

No abstract available.

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Ishikawa T, Hino K, Yoneda T, et al. Air Oxidation of 2-Aryl-1-tetralones in Basic, Neutral, and Acidic Media: An Unprecedented Oxidative Aryl Migration to 2-Aryloxy-1-naphthols under Acidic Condition. J Org Chem. 1999;64(15):5691-5695doi: 10.1021/jo9824854.
Ishikawa, T., Hino, K., Yoneda, T., Murota, M., Yamaguchi, K., & Watanabe, T. (1999). Air Oxidation of 2-Aryl-1-tetralones in Basic, Neutral, and Acidic Media: An Unprecedented Oxidative Aryl Migration to 2-Aryloxy-1-naphthols under Acidic Condition. The Journal of organic chemistry, 64(15), 5691-5695. https://doi.org/10.1021/jo9824854
Ishikawa, Tsutomu, et al. "Air Oxidation of 2-Aryl-1-tetralones in Basic, Neutral, and Acidic Media: An Unprecedented Oxidative Aryl Migration to 2-Aryloxy-1-naphthols under Acidic Condition." The Journal of organic chemistry vol. 64,15 (1999): 5691-5695. doi: https://doi.org/10.1021/jo9824854
Ishikawa T, Hino K, Yoneda T, Murota M, Yamaguchi K, Watanabe T. Air Oxidation of 2-Aryl-1-tetralones in Basic, Neutral, and Acidic Media: An Unprecedented Oxidative Aryl Migration to 2-Aryloxy-1-naphthols under Acidic Condition. J Org Chem. 1999 Jul 23;64(15):5691-5695. doi: 10.1021/jo9824854. PMID: 11674642.
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Ruthenium-catalyzed cycloaddition of propargylic alcohols with phenol derivatives via allenylidene intermediates: catalytic use of the allenylidene ligand as the C(3) unit.

Journal of the American Chemical Society

Nishibayashi Y, Inada Y, Hidai M, Uemura S.
PMID: 12095324
J Am Chem Soc. 2002 Jul 10;124(27):7900-1. doi: 10.1021/ja026168x.

Novel ruthenium-catalyzed cycloaddition of propargylic alcohols with 2-naphthols and phenols bearing electron-donating groups via allenylidene intermediates has been developed to give the corresponding 1H-naphtho[2,1-b]pyrans and 4H-1-benzopyrans, respectively, in moderate to excellent yields with complete regioselectivity.

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Nishibayashi Y, Inada Y, Hidai M, et al. Ruthenium-catalyzed cycloaddition of propargylic alcohols with phenol derivatives via allenylidene intermediates: catalytic use of the allenylidene ligand as the C(3) unit. J Am Chem Soc. 2002;124(27):7900-1doi: 10.1021/ja026168x.
Nishibayashi, Y., Inada, Y., Hidai, M., & Uemura, S. (2002). Ruthenium-catalyzed cycloaddition of propargylic alcohols with phenol derivatives via allenylidene intermediates: catalytic use of the allenylidene ligand as the C(3) unit. Journal of the American Chemical Society, 124(27), 7900-1. https://doi.org/10.1021/ja026168x
Nishibayashi, Yoshiaki, et al. "Ruthenium-catalyzed cycloaddition of propargylic alcohols with phenol derivatives via allenylidene intermediates: catalytic use of the allenylidene ligand as the C(3) unit." Journal of the American Chemical Society vol. 124,27 (2002): 7900-1. doi: https://doi.org/10.1021/ja026168x
Nishibayashi Y, Inada Y, Hidai M, Uemura S. Ruthenium-catalyzed cycloaddition of propargylic alcohols with phenol derivatives via allenylidene intermediates: catalytic use of the allenylidene ligand as the C(3) unit. J Am Chem Soc. 2002 Jul 10;124(27):7900-1. doi: 10.1021/ja026168x. PMID: 12095324.
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Catalytic Activities of CuSO(4)/Al(2)O(3) in Dehydrogenation of Arenes by Dioxygen.

The Journal of organic chemistry

Sakamoto T, Yonehara H, Pac C.
PMID: 11671703
J Org Chem. 1997 May 16;62(10):3194-3199. doi: 10.1021/jo961377j.

The oxidation reactions of hydroquinones, 2-naphthols, or 2,6-di-tert-butylphenol efficiently occurred by catalysis with alumina-supported copper(II) sulfate to give the corresponding benzoquinones, 1,1'-bi-2-naphthols, and 4,4'-diphenoquinone, respectively, in good yields. The synthetic potentiality of the catalytic reactions was demonstrated by easy...

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Sakamoto T, Yonehara H, Pac C. Catalytic Activities of CuSO(4)/Al(2)O(3) in Dehydrogenation of Arenes by Dioxygen. J Org Chem. 1997;62(10):3194-3199doi: 10.1021/jo961377j.
Sakamoto, T., Yonehara, H., & Pac, C. (1997). Catalytic Activities of CuSO(4)/Al(2)O(3) in Dehydrogenation of Arenes by Dioxygen. The Journal of organic chemistry, 62(10), 3194-3199. https://doi.org/10.1021/jo961377j
Sakamoto, Takaaki, et al. "Catalytic Activities of CuSO(4)/Al(2)O(3) in Dehydrogenation of Arenes by Dioxygen." The Journal of organic chemistry vol. 62,10 (1997): 3194-3199. doi: https://doi.org/10.1021/jo961377j
Sakamoto T, Yonehara H, Pac C. Catalytic Activities of CuSO(4)/Al(2)O(3) in Dehydrogenation of Arenes by Dioxygen. J Org Chem. 1997 May 16;62(10):3194-3199. doi: 10.1021/jo961377j. PMID: 11671703.
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