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Functionalization of Azacalixaromatics by Cu(II)-Catalyzed Oxidative Cross-Coupling Reaction between the Arene C-H Bond and Boronic Acids.

Organic letters

Liu Y, Long C, Zhao L, Wang MX.
PMID: 27624604
Org Lett. 2016 Oct 07;18(19):5078-5081. doi: 10.1021/acs.orglett.6b02530. Epub 2016 Sep 14.

Catalyzed by Cu(ClO

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Liu Y, Long C, Zhao L, et al. Functionalization of Azacalixaromatics by Cu(II)-Catalyzed Oxidative Cross-Coupling Reaction between the Arene C-H Bond and Boronic Acids. Org Lett. 2016;18(19):5078-5081doi: 10.1021/acs.orglett.6b02530.
Liu, Y., Long, C., Zhao, L., & Wang, M. X. (2016). Functionalization of Azacalixaromatics by Cu(II)-Catalyzed Oxidative Cross-Coupling Reaction between the Arene C-H Bond and Boronic Acids. Organic letters, 18(19), 5078-5081. https://doi.org/10.1021/acs.orglett.6b02530
Liu, Yang, et al. "Functionalization of Azacalixaromatics by Cu(II)-Catalyzed Oxidative Cross-Coupling Reaction between the Arene C-H Bond and Boronic Acids." Organic letters vol. 18,19 (2016): 5078-5081. doi: https://doi.org/10.1021/acs.orglett.6b02530
Liu Y, Long C, Zhao L, Wang MX. Functionalization of Azacalixaromatics by Cu(II)-Catalyzed Oxidative Cross-Coupling Reaction between the Arene C-H Bond and Boronic Acids. Org Lett. 2016 Oct 07;18(19):5078-5081. doi: 10.1021/acs.orglett.6b02530. Epub 2016 Sep 14. PMID: 27624604.
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Selective and Serial Suzuki-Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters.

Organic letters

Laulhé S, Blackburn JM, Roizen JL.
PMID: 27537216
Org Lett. 2016 Sep 02;18(17):4440-3. doi: 10.1021/acs.orglett.6b02323. Epub 2016 Aug 18.

Among cross-coupling reactions, the Suzuki-Miyaura transformation stands out because of its practical advantages, including the commercial availability and low toxicity of the required reagents, mild reaction conditions, and functional group compatibility. Nevertheless, few conditions can be used to cross-couple...

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Laulhé S, Blackburn JM, Roizen JL. Selective and Serial Suzuki-Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters. Org Lett. 2016;18(17):4440-3doi: 10.1021/acs.orglett.6b02323.
Laulhé, S., Blackburn, J. M., & Roizen, J. L. (2016). Selective and Serial Suzuki-Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters. Organic letters, 18(17), 4440-3. https://doi.org/10.1021/acs.orglett.6b02323
Laulhé, Sébastien, et al. "Selective and Serial Suzuki-Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters." Organic letters vol. 18,17 (2016): 4440-3. doi: https://doi.org/10.1021/acs.orglett.6b02323
Laulhé S, Blackburn JM, Roizen JL. Selective and Serial Suzuki-Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters. Org Lett. 2016 Sep 02;18(17):4440-3. doi: 10.1021/acs.orglett.6b02323. Epub 2016 Aug 18. PMID: 27537216; PMCID: PMC5433267.
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"Cationic" Suzuki-Miyaura Coupling with Acutely Base-Sensitive Boronic Acids.

Journal of the American Chemical Society

Chen L, Sanchez DR, Zhang B, Carrow BP.
PMID: 28862445
J Am Chem Soc. 2017 Sep 13;139(36):12418-12421. doi: 10.1021/jacs.7b07687. Epub 2017 Sep 05.

Fast, base-promoted protodeboronation of polyfluoroaryl and heteroaryl boronic acids complicates their use in Suzuki-Miyaura coupling (SMC) because a base is generally required for catalysis. We report a "cationic" SMC method using a PAd

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Chen L, Sanchez DR, Zhang B, et al. "Cationic" Suzuki-Miyaura Coupling with Acutely Base-Sensitive Boronic Acids. J Am Chem Soc. 2017;139(36):12418-12421doi: 10.1021/jacs.7b07687.
Chen, L., Sanchez, D. R., Zhang, B., & Carrow, B. P. (2017). "Cationic" Suzuki-Miyaura Coupling with Acutely Base-Sensitive Boronic Acids. Journal of the American Chemical Society, 139(36), 12418-12421. https://doi.org/10.1021/jacs.7b07687
Chen, Liye, et al. ""Cationic" Suzuki-Miyaura Coupling with Acutely Base-Sensitive Boronic Acids." Journal of the American Chemical Society vol. 139,36 (2017): 12418-12421. doi: https://doi.org/10.1021/jacs.7b07687
Chen L, Sanchez DR, Zhang B, Carrow BP. "Cationic" Suzuki-Miyaura Coupling with Acutely Base-Sensitive Boronic Acids. J Am Chem Soc. 2017 Sep 13;139(36):12418-12421. doi: 10.1021/jacs.7b07687. Epub 2017 Sep 05. PMID: 28862445.
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Palladium-Catalyzed Enantioselective Three-Component Synthesis of α-Arylglycines.

Organic letters

Beisel T, Diehl AM, Manolikakes G.
PMID: 27505131
Org Lett. 2016 Aug 19;18(16):4116-9. doi: 10.1021/acs.orglett.6b02045. Epub 2016 Aug 09.

A general Pd-catalyzed, enantioselective three-component synthesis of α-arylglycines starting from sulfonamides, glyoxylic acid derivatives, and boronic acids was developed. This operationally straightforward procedure enables the preparation of a wide variety of α-arylglycines in high yields and excellent levels of...

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Beisel T, Diehl AM, Manolikakes G. Palladium-Catalyzed Enantioselective Three-Component Synthesis of α-Arylglycines. Org Lett. 2016;18(16):4116-9doi: 10.1021/acs.orglett.6b02045.
Beisel, T., Diehl, A. M., & Manolikakes, G. (2016). Palladium-Catalyzed Enantioselective Three-Component Synthesis of α-Arylglycines. Organic letters, 18(16), 4116-9. https://doi.org/10.1021/acs.orglett.6b02045
Beisel, Tamara, et al. "Palladium-Catalyzed Enantioselective Three-Component Synthesis of α-Arylglycines." Organic letters vol. 18,16 (2016): 4116-9. doi: https://doi.org/10.1021/acs.orglett.6b02045
Beisel T, Diehl AM, Manolikakes G. Palladium-Catalyzed Enantioselective Three-Component Synthesis of α-Arylglycines. Org Lett. 2016 Aug 19;18(16):4116-9. doi: 10.1021/acs.orglett.6b02045. Epub 2016 Aug 09. PMID: 27505131.
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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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Shape-Controlled Synthesis and Self-Sorting of Covalent Organic Cage Compounds.

Angewandte Chemie (International ed. in English)

Klotzbach S, Beuerle F.
PMID: 26136295
Angew Chem Int Ed Engl. 2015 Aug 24;54(35):10356-60. doi: 10.1002/anie.201502983. Epub 2015 Jul 01.

The directional bonding approach is a powerful tool to rationally control both shape and stoichiometry of three-dimensional objects built from rigid building blocks under dynamic covalent conditions. Co-condensation of catechol-functionalized tribenzotriquinacene derivatives which have 90° angles between the reactive...

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Klotzbach S, Beuerle F. Shape-Controlled Synthesis and Self-Sorting of Covalent Organic Cage Compounds. Angew Chem Int Ed Engl. 2015;54(35):10356-60doi: 10.1002/anie.201502983.
Klotzbach, S., & Beuerle, F. (2015). Shape-Controlled Synthesis and Self-Sorting of Covalent Organic Cage Compounds. Angewandte Chemie (International ed. in English), 54(35), 10356-60. https://doi.org/10.1002/anie.201502983
Klotzbach, Stefanie, and Beuerle, Florian. "Shape-Controlled Synthesis and Self-Sorting of Covalent Organic Cage Compounds." Angewandte Chemie (International ed. in English) vol. 54,35 (2015): 10356-60. doi: https://doi.org/10.1002/anie.201502983
Klotzbach S, Beuerle F. Shape-Controlled Synthesis and Self-Sorting of Covalent Organic Cage Compounds. Angew Chem Int Ed Engl. 2015 Aug 24;54(35):10356-60. doi: 10.1002/anie.201502983. Epub 2015 Jul 01. PMID: 26136295.
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The role of boronic acids in accelerating condensation reactions of α-effect amines with carbonyls.

Organic & biomolecular chemistry

Gillingham D.
PMID: 27424916
Org Biomol Chem. 2016 Aug 10;14(32):7606-9. doi: 10.1039/c6ob01193d.

A broad palette of bioconjugation reactions are available for chemical biologists, but an area that still requires investigation is high-rate constant reactions. These are indispensable in certain applications, particularly for in vivo labelling. Appropriately positioned boronic acids accelerate normally...

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Gillingham D. The role of boronic acids in accelerating condensation reactions of α-effect amines with carbonyls. Org Biomol Chem. 2016;14(32):7606-9doi: 10.1039/c6ob01193d.
Gillingham, D. (2016). The role of boronic acids in accelerating condensation reactions of α-effect amines with carbonyls. Organic & biomolecular chemistry, 14(32), 7606-9. https://doi.org/10.1039/c6ob01193d
Gillingham, Dennis. "The role of boronic acids in accelerating condensation reactions of α-effect amines with carbonyls." Organic & biomolecular chemistry vol. 14,32 (2016): 7606-9. doi: https://doi.org/10.1039/c6ob01193d
Gillingham D. The role of boronic acids in accelerating condensation reactions of α-effect amines with carbonyls. Org Biomol Chem. 2016 Aug 10;14(32):7606-9. doi: 10.1039/c6ob01193d. PMID: 27424916.
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Tandem Coupling of Azide with Isonitrile and Boronic Acid: Facile Access to Functionalized Amidines.

Angewandte Chemie (International ed. in English)

Zhang Z, Huang B, Qiao G, Zhu L, Xiao F, Chen F, Fu B, Zhang Z.
PMID: 28319297
Angew Chem Int Ed Engl. 2017 Apr 03;56(15):4320-4323. doi: 10.1002/anie.201700539. Epub 2017 Mar 20.

Amidine is a notable nitrogen-containing structural motif found in bioactive natural products and pharmaceuticals. Herein, a novel rhodium(I)-catalyzed tandem reaction of readily accessible azides with isonitriles and boronic acids via a carbodiimide intermediate is achieved. This protocol offers an...

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Zhang Z, Huang B, Qiao G, et al. Tandem Coupling of Azide with Isonitrile and Boronic Acid: Facile Access to Functionalized Amidines. Angew Chem Int Ed Engl. 2017;56(15):4320-4323doi: 10.1002/anie.201700539.
Zhang, Z., Huang, B., Qiao, G., Zhu, L., Xiao, F., Chen, F., Fu, B., & Zhang, Z. (2017). Tandem Coupling of Azide with Isonitrile and Boronic Acid: Facile Access to Functionalized Amidines. Angewandte Chemie (International ed. in English), 56(15), 4320-4323. https://doi.org/10.1002/anie.201700539
Zhang, Zhen, et al. "Tandem Coupling of Azide with Isonitrile and Boronic Acid: Facile Access to Functionalized Amidines." Angewandte Chemie (International ed. in English) vol. 56,15 (2017): 4320-4323. doi: https://doi.org/10.1002/anie.201700539
Zhang Z, Huang B, Qiao G, Zhu L, Xiao F, Chen F, Fu B, Zhang Z. Tandem Coupling of Azide with Isonitrile and Boronic Acid: Facile Access to Functionalized Amidines. Angew Chem Int Ed Engl. 2017 Apr 03;56(15):4320-4323. doi: 10.1002/anie.201700539. Epub 2017 Mar 20. PMID: 28319297.
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Regioselective synthesis of 2-(bromomethyl)-5-aryl-thiophene derivatives via palladium (0) catalyzed suzuki cross-coupling reactions: as antithrombotic and haemolytically active molecules.

Chemistry Central journal

Rizwan K, Zubair M, Rasool N, Ali S, Zahoor AF, Rana UA, Khan SU, Shahid M, Zia-Ul-Haq M, Jaafar HZ.
PMID: 25685184
Chem Cent J. 2014 Dec 17;8:74. doi: 10.1186/s13065-014-0074-z. eCollection 2014.

BACKGROUND: It is seen that the regioselective functionalizations of halogenated heterocycles play an important role in the synthesis of several types of organic compounds. In this domain, the Suzuki-Miyaura reaction has emerged as a convenient way to build carbon-carbon...

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Rizwan K, Zubair M, Rasool N, et al. Regioselective synthesis of 2-(bromomethyl)-5-aryl-thiophene derivatives via palladium (0) catalyzed suzuki cross-coupling reactions: as antithrombotic and haemolytically active molecules. Chem Cent J. 2014;8:74doi: 10.1186/s13065-014-0074-z.
Rizwan, K., Zubair, M., Rasool, N., Ali, S., Zahoor, A. F., Rana, U. A., Khan, S. U., Shahid, M., Zia-Ul-Haq, M., & Jaafar, H. Z. (2014). Regioselective synthesis of 2-(bromomethyl)-5-aryl-thiophene derivatives via palladium (0) catalyzed suzuki cross-coupling reactions: as antithrombotic and haemolytically active molecules. Chemistry Central journal, 874. https://doi.org/10.1186/s13065-014-0074-z
Rizwan, Komal, et al. "Regioselective synthesis of 2-(bromomethyl)-5-aryl-thiophene derivatives via palladium (0) catalyzed suzuki cross-coupling reactions: as antithrombotic and haemolytically active molecules." Chemistry Central journal vol. 8 (2014): 74. doi: https://doi.org/10.1186/s13065-014-0074-z
Rizwan K, Zubair M, Rasool N, Ali S, Zahoor AF, Rana UA, Khan SU, Shahid M, Zia-Ul-Haq M, Jaafar HZ. Regioselective synthesis of 2-(bromomethyl)-5-aryl-thiophene derivatives via palladium (0) catalyzed suzuki cross-coupling reactions: as antithrombotic and haemolytically active molecules. Chem Cent J. 2014 Dec 17;8:74. doi: 10.1186/s13065-014-0074-z. eCollection 2014. PMID: 25685184; PMCID: PMC4326645.
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Simple and Efficient Generation of Aryl Radicals from Aryl Triflates: Synthesis of Aryl Boronates and Aryl Iodides at Room Temperature.

Journal of the American Chemical Society

Liu W, Yang X, Gao Y, Li CJ.
PMID: 28578579
J Am Chem Soc. 2017 Jun 28;139(25):8621-8627. doi: 10.1021/jacs.7b03538. Epub 2017 Jun 20.

Despite the wide use of aryl radicals in organic synthesis, current methods to prepare them from aryl halides, carboxylic acids, boronic acids, and diazonium salts suffer from limitations. Aryl triflates, easily obtained from phenols, are promising aryl radical progenitors...

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Liu W, Yang X, Gao Y, et al. Simple and Efficient Generation of Aryl Radicals from Aryl Triflates: Synthesis of Aryl Boronates and Aryl Iodides at Room Temperature. J Am Chem Soc. 2017;139(25):8621-8627doi: 10.1021/jacs.7b03538.
Liu, W., Yang, X., Gao, Y., & Li, C. J. (2017). Simple and Efficient Generation of Aryl Radicals from Aryl Triflates: Synthesis of Aryl Boronates and Aryl Iodides at Room Temperature. Journal of the American Chemical Society, 139(25), 8621-8627. https://doi.org/10.1021/jacs.7b03538
Liu, Wenbo, et al. "Simple and Efficient Generation of Aryl Radicals from Aryl Triflates: Synthesis of Aryl Boronates and Aryl Iodides at Room Temperature." Journal of the American Chemical Society vol. 139,25 (2017): 8621-8627. doi: https://doi.org/10.1021/jacs.7b03538
Liu W, Yang X, Gao Y, Li CJ. Simple and Efficient Generation of Aryl Radicals from Aryl Triflates: Synthesis of Aryl Boronates and Aryl Iodides at Room Temperature. J Am Chem Soc. 2017 Jun 28;139(25):8621-8627. doi: 10.1021/jacs.7b03538. Epub 2017 Jun 20. PMID: 28578579.
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Palladium and visible-light mediated carbonylative Suzuki-Miyaura coupling of unactivated alkyl halides and aryl boronic acids.

Chemical communications (Cambridge, England)

Roslin S, Odell LR.
PMID: 28607963
Chem Commun (Camb). 2017 Jun 22;53(51):6895-6898. doi: 10.1039/c7cc02763j.

Herein, a simple and efficient method for the palladium-catalyzed carbonylation of aryl boronic acids with unactivated alkyl iodides and bromides under visible-light irradiation, ambient temperature and low CO-pressure is presented. Notably, the procedure uses readily available equipment and an...

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Roslin S, Odell LR. Palladium and visible-light mediated carbonylative Suzuki-Miyaura coupling of unactivated alkyl halides and aryl boronic acids. Chem Commun (Camb). 2017;53(51):6895-6898doi: 10.1039/c7cc02763j.
Roslin, S., & Odell, L. R. (2017). Palladium and visible-light mediated carbonylative Suzuki-Miyaura coupling of unactivated alkyl halides and aryl boronic acids. Chemical communications (Cambridge, England), 53(51), 6895-6898. https://doi.org/10.1039/c7cc02763j
Roslin, Sara, and Odell, Luke R. "Palladium and visible-light mediated carbonylative Suzuki-Miyaura coupling of unactivated alkyl halides and aryl boronic acids." Chemical communications (Cambridge, England) vol. 53,51 (2017): 6895-6898. doi: https://doi.org/10.1039/c7cc02763j
Roslin S, Odell LR. Palladium and visible-light mediated carbonylative Suzuki-Miyaura coupling of unactivated alkyl halides and aryl boronic acids. Chem Commun (Camb). 2017 Jun 22;53(51):6895-6898. doi: 10.1039/c7cc02763j. PMID: 28607963.
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Novel pyridine-based Pd(II)-complex for efficient Suzuki coupling of aryl halides under microwaves irradiation in water.

Chemistry Central journal

Althagafi II, Shaaban MR, Al-Dawood AY, Farag AM.
PMID: 29086871
Chem Cent J. 2017 Sep 18;11(1):88. doi: 10.1186/s13065-017-0320-2.

Suzuki C-C cross-coupling of aryl halides with aryl boronic acids using new phosphene-free palladium complexes as precatalysts was investigated. A pyridine-based Pd(II)-complex was used in open air under thermal as well as microwave irradiation conditions using water as an...

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Althagafi II, Shaaban MR, Al-Dawood AY, et al. Novel pyridine-based Pd(II)-complex for efficient Suzuki coupling of aryl halides under microwaves irradiation in water. Chem Cent J. 2017;11(1):88doi: 10.1186/s13065-017-0320-2.
Althagafi, I. I., Shaaban, M. R., Al-Dawood, A. Y., & Farag, A. M. (2017). Novel pyridine-based Pd(II)-complex for efficient Suzuki coupling of aryl halides under microwaves irradiation in water. Chemistry Central journal, 11(1), 88. https://doi.org/10.1186/s13065-017-0320-2
Althagafi, Ismail I, et al. "Novel pyridine-based Pd(II)-complex for efficient Suzuki coupling of aryl halides under microwaves irradiation in water." Chemistry Central journal vol. 11,1 (2017): 88. doi: https://doi.org/10.1186/s13065-017-0320-2
Althagafi II, Shaaban MR, Al-Dawood AY, Farag AM. Novel pyridine-based Pd(II)-complex for efficient Suzuki coupling of aryl halides under microwaves irradiation in water. Chem Cent J. 2017 Sep 18;11(1):88. doi: 10.1186/s13065-017-0320-2. PMID: 29086871; PMCID: PMC5603456.
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Showing 1 to 12 of 667 entries