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Synthesis of Phenylpropanoids via Matsuda-Heck Coupling of Arene Diazonium Salts.

The Journal of organic chemistry

Schmidt B, Wolf F.
PMID: 28394127
J Org Chem. 2017 Apr 21;82(8):4386-4395. doi: 10.1021/acs.joc.7b00447. Epub 2017 Apr 13.

The Pd-catalyzed Heck-type coupling (Matsuda-Heck reaction) of electron rich arene diazonium salts with electron deficient olefins has been exploited for the synthesis of phenylpropanoid natural products. Examples described herein are the naturally occurring benzofurans methyl wutaifuranate, wutaifuranol, wutaifuranal, their...

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Schmidt B, Wolf F. Synthesis of Phenylpropanoids via Matsuda-Heck Coupling of Arene Diazonium Salts. J Org Chem. 2017;82(8):4386-4395doi: 10.1021/acs.joc.7b00447.
Schmidt, B., & Wolf, F. (2017). Synthesis of Phenylpropanoids via Matsuda-Heck Coupling of Arene Diazonium Salts. The Journal of organic chemistry, 82(8), 4386-4395. https://doi.org/10.1021/acs.joc.7b00447
Schmidt, Bernd, and Wolf, Felix. "Synthesis of Phenylpropanoids via Matsuda-Heck Coupling of Arene Diazonium Salts." The Journal of organic chemistry vol. 82,8 (2017): 4386-4395. doi: https://doi.org/10.1021/acs.joc.7b00447
Schmidt B, Wolf F. Synthesis of Phenylpropanoids via Matsuda-Heck Coupling of Arene Diazonium Salts. J Org Chem. 2017 Apr 21;82(8):4386-4395. doi: 10.1021/acs.joc.7b00447. Epub 2017 Apr 13. PMID: 28394127.
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Divergence in the reactivity between amine- and phosphine-catalyzed cycloaddition reactions of allenoates with enynals: one-pot gold-catalyzed synthesis of trisubstituted benzofurans from the [3 + 2] cycloadduct via 1,2-alkyl migration and dehydrogenation.

The Journal of organic chemistry

Kumari AL, Swamy KC.
PMID: 25793444
J Org Chem. 2015 Apr 17;80(8):4084-96. doi: 10.1021/acs.joc.5b00415. Epub 2015 Mar 31.

Regioselective synthesis of functionalized dihydropyran derivatives by DABCO-catalyzed [2 + 4] cycloaddition of allenoates with enynals or enynones has been developed. Phosphine-catalyzed [3 + 2] cycloaddition of allenoates with enynals provides 1,1-alkyne (aldehyde)-substituted cyclopentenes wherein enynals act as electrophiles....

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Kumari AL, Swamy KC. Divergence in the reactivity between amine- and phosphine-catalyzed cycloaddition reactions of allenoates with enynals: one-pot gold-catalyzed synthesis of trisubstituted benzofurans from the [3 + 2] cycloadduct via 1,2-alkyl migration and dehydrogenation. J Org Chem. 2015;80(8):4084-96doi: 10.1021/acs.joc.5b00415.
Kumari, A. L., & Swamy, K. C. (2015). Divergence in the reactivity between amine- and phosphine-catalyzed cycloaddition reactions of allenoates with enynals: one-pot gold-catalyzed synthesis of trisubstituted benzofurans from the [3 + 2] cycloadduct via 1,2-alkyl migration and dehydrogenation. The Journal of organic chemistry, 80(8), 4084-96. https://doi.org/10.1021/acs.joc.5b00415
Kumari, A Leela Siva, and Swamy, K C Kumara. "Divergence in the reactivity between amine- and phosphine-catalyzed cycloaddition reactions of allenoates with enynals: one-pot gold-catalyzed synthesis of trisubstituted benzofurans from the [3 + 2] cycloadduct via 1,2-alkyl migration and dehydrogenation." The Journal of organic chemistry vol. 80,8 (2015): 4084-96. doi: https://doi.org/10.1021/acs.joc.5b00415
Kumari AL, Swamy KC. Divergence in the reactivity between amine- and phosphine-catalyzed cycloaddition reactions of allenoates with enynals: one-pot gold-catalyzed synthesis of trisubstituted benzofurans from the [3 + 2] cycloadduct via 1,2-alkyl migration and dehydrogenation. J Org Chem. 2015 Apr 17;80(8):4084-96. doi: 10.1021/acs.joc.5b00415. Epub 2015 Mar 31. PMID: 25793444.
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Silver/Scandium-Cocatalyzed Bicyclization of β-Alkynyl Ketones Leading to Benzo[c]xanthenes and Naphtho[1,2-b]benzofurans.

The Journal of organic chemistry

Chen K, Liu S, Wang D, Hao WJ, Zhou P, Tu SJ, Jiang B.
PMID: 29028339
J Org Chem. 2017 Nov 03;82(21):11524-11530. doi: 10.1021/acs.joc.7b02134.

The combination of AgTFA and Sc(OTf)

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Chen K, Liu S, Wang D, et al. Silver/Scandium-Cocatalyzed Bicyclization of β-Alkynyl Ketones Leading to Benzo[c]xanthenes and Naphtho[1,2-b]benzofurans. J Org Chem. 2017;82(21):11524-11530doi: 10.1021/acs.joc.7b02134.
Chen, K., Liu, S., Wang, D., Hao, W. J., Zhou, P., Tu, S. J., & Jiang, B. (2017). Silver/Scandium-Cocatalyzed Bicyclization of β-Alkynyl Ketones Leading to Benzo[c]xanthenes and Naphtho[1,2-b]benzofurans. The Journal of organic chemistry, 82(21), 11524-11530. https://doi.org/10.1021/acs.joc.7b02134
Chen, Ke, et al. "Silver/Scandium-Cocatalyzed Bicyclization of β-Alkynyl Ketones Leading to Benzo[c]xanthenes and Naphtho[1,2-b]benzofurans." The Journal of organic chemistry vol. 82,21 (2017): 11524-11530. doi: https://doi.org/10.1021/acs.joc.7b02134
Chen K, Liu S, Wang D, Hao WJ, Zhou P, Tu SJ, Jiang B. Silver/Scandium-Cocatalyzed Bicyclization of β-Alkynyl Ketones Leading to Benzo[c]xanthenes and Naphtho[1,2-b]benzofurans. J Org Chem. 2017 Nov 03;82(21):11524-11530. doi: 10.1021/acs.joc.7b02134. PMID: 29028339.
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Palladium-catalyzed synthesis of [60]fullerene-fused benzofurans via heteroannulation of phenols.

Chemical communications (Cambridge, England)

Li F, Wang JJ, Wang GW.
PMID: 28111656
Chem Commun (Camb). 2017 Feb 02;53(11):1852-1855. doi: 10.1039/c6cc09080j.

Palladium-catalyzed heteroannulation of [60]fullerene with phenols has been developed as a practical and efficient protocol for the one-pot synthesis of various [60]fullerene-fused benzofurans. A possible reaction mechanism is proposed to explain the formation of C

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Li F, Wang JJ, Wang GW. Palladium-catalyzed synthesis of [60]fullerene-fused benzofurans via heteroannulation of phenols. Chem Commun (Camb). 2017;53(11):1852-1855doi: 10.1039/c6cc09080j.
Li, F., Wang, J. J., & Wang, G. W. (2017). Palladium-catalyzed synthesis of [60]fullerene-fused benzofurans via heteroannulation of phenols. Chemical communications (Cambridge, England), 53(11), 1852-1855. https://doi.org/10.1039/c6cc09080j
Li, Fei, et al. "Palladium-catalyzed synthesis of [60]fullerene-fused benzofurans via heteroannulation of phenols." Chemical communications (Cambridge, England) vol. 53,11 (2017): 1852-1855. doi: https://doi.org/10.1039/c6cc09080j
Li F, Wang JJ, Wang GW. Palladium-catalyzed synthesis of [60]fullerene-fused benzofurans via heteroannulation of phenols. Chem Commun (Camb). 2017 Feb 02;53(11):1852-1855. doi: 10.1039/c6cc09080j. PMID: 28111656.
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Synthetic Transformations through Alkynoxy-Palladium Interactions and C-H Activation.

Accounts of chemical research

Minami Y, Hiyama T.
PMID: 26651014
Acc Chem Res. 2016 Jan 19;49(1):67-77. doi: 10.1021/acs.accounts.5b00414. Epub 2015 Dec 09.

Organic synthesis based on straightforward transformations is essential for environmentally benign manufacturing for the invention of novel pharmaceuticals, agrochemicals, and organoelectronic materials in order to ultimately realize a sustainable society. Metal-catalyzed C-H bond-cleaving functionalization has become a promising method...

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Minami Y, Hiyama T. Synthetic Transformations through Alkynoxy-Palladium Interactions and C-H Activation. Acc Chem Res. 2015;49(1):67-77doi: 10.1021/acs.accounts.5b00414.
Minami, Y., & Hiyama, T. (2016). Synthetic Transformations through Alkynoxy-Palladium Interactions and C-H Activation. Accounts of chemical research, 49(1), 67-77. https://doi.org/10.1021/acs.accounts.5b00414
Minami, Yasunori, and Hiyama, Tamejiro. "Synthetic Transformations through Alkynoxy-Palladium Interactions and C-H Activation." Accounts of chemical research vol. 49,1 (2016): 67-77. doi: https://doi.org/10.1021/acs.accounts.5b00414
Minami Y, Hiyama T. Synthetic Transformations through Alkynoxy-Palladium Interactions and C-H Activation. Acc Chem Res. 2016 Jan 19;49(1):67-77. doi: 10.1021/acs.accounts.5b00414. Epub 2015 Dec 09. PMID: 26651014.
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Synthesis of 2,3-Disubstituted Indoles and Benzofurans by the Tandem Reaction of Rhodium(II)-Catalyzed Intramolecular C-H Insertion and Oxygen-Mediated Oxidation.

The Journal of organic chemistry

Shen H, Fu J, Yuan H, Gong J, Yang Z.
PMID: 27171797
J Org Chem. 2016 Nov 04;81(21):10180-10192. doi: 10.1021/acs.joc.6b00611. Epub 2016 May 24.

A highly effective and straightforward method to construct a wide range of functionalized 2,3-disubstituted indoles has been developed. The method involves the tandem reaction of rhodium(II)-catalyzed denitrogenative annulation of triazole-based benzyl anilines and oxygen-mediated oxidative aromatization. The developed method...

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Shen H, Fu J, Yuan H, et al. Synthesis of 2,3-Disubstituted Indoles and Benzofurans by the Tandem Reaction of Rhodium(II)-Catalyzed Intramolecular C-H Insertion and Oxygen-Mediated Oxidation. J Org Chem. 2016;81(21):10180-10192doi: 10.1021/acs.joc.6b00611.
Shen, H., Fu, J., Yuan, H., Gong, J., & Yang, Z. (2016). Synthesis of 2,3-Disubstituted Indoles and Benzofurans by the Tandem Reaction of Rhodium(II)-Catalyzed Intramolecular C-H Insertion and Oxygen-Mediated Oxidation. The Journal of organic chemistry, 81(21), 10180-10192. https://doi.org/10.1021/acs.joc.6b00611
Shen, Hongjuan, et al. "Synthesis of 2,3-Disubstituted Indoles and Benzofurans by the Tandem Reaction of Rhodium(II)-Catalyzed Intramolecular C-H Insertion and Oxygen-Mediated Oxidation." The Journal of organic chemistry vol. 81,21 (2016): 10180-10192. doi: https://doi.org/10.1021/acs.joc.6b00611
Shen H, Fu J, Yuan H, Gong J, Yang Z. Synthesis of 2,3-Disubstituted Indoles and Benzofurans by the Tandem Reaction of Rhodium(II)-Catalyzed Intramolecular C-H Insertion and Oxygen-Mediated Oxidation. J Org Chem. 2016 Nov 04;81(21):10180-10192. doi: 10.1021/acs.joc.6b00611. Epub 2016 May 24. PMID: 27171797.
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Palladium-Catalyzed Synthesis of 2,3-Disubstituted Benzofurans: An Approach Towards the Synthesis of Deuterium Labeled Compounds.

Advanced synthesis & catalysis

Agasti S, Maity S, Szabo KJ, Maiti D.
PMID: 26347405
Adv Synth Catal. 2015 Jul 06;357(10):2331-2338. doi: 10.1002/adsc.201500308. Epub 2015 Jul 14.

Palladium-catalyzed oxidative annulations between phenols and alkenylcarboxylic acids produced a library of benzofuran compounds. Depending on the nature of the substitution of the phenol precursor, either 2,3-dialkylbenzofurans or 2-alkyl-3-methylene-2,3-dihydrobenzofurans can be synthesized with excellent regioselectivity. Reactions between conjugated 5-phenylpenta-2,4-dienoic...

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Agasti S, Maity S, Szabo KJ, et al. Palladium-Catalyzed Synthesis of 2,3-Disubstituted Benzofurans: An Approach Towards the Synthesis of Deuterium Labeled Compounds. Adv Synth Catal. 2015;357(10):2331-2338doi: 10.1002/adsc.201500308.
Agasti, S., Maity, S., Szabo, K. J., & Maiti, D. (2015). Palladium-Catalyzed Synthesis of 2,3-Disubstituted Benzofurans: An Approach Towards the Synthesis of Deuterium Labeled Compounds. Advanced synthesis & catalysis, 357(10), 2331-2338. https://doi.org/10.1002/adsc.201500308
Agasti, Soumitra, et al. "Palladium-Catalyzed Synthesis of 2,3-Disubstituted Benzofurans: An Approach Towards the Synthesis of Deuterium Labeled Compounds." Advanced synthesis & catalysis vol. 357,10 (2015): 2331-2338. doi: https://doi.org/10.1002/adsc.201500308
Agasti S, Maity S, Szabo KJ, Maiti D. Palladium-Catalyzed Synthesis of 2,3-Disubstituted Benzofurans: An Approach Towards the Synthesis of Deuterium Labeled Compounds. Adv Synth Catal. 2015 Jul 06;357(10):2331-2338. doi: 10.1002/adsc.201500308. Epub 2015 Jul 14. PMID: 26347405; PMCID: PMC4552971.
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Synthesis of 2-substituted benzofurans and indoles using functionalized titanium benzylidene reagents on solid phase.

The Journal of organic chemistry

Macleod C, McKiernan GJ, Guthrie EJ, Farrugia LJ, Hamprecht DW, Macritchie J, Hartley RC.
PMID: 12530864
J Org Chem. 2003 Jan 24;68(2):387-401. doi: 10.1021/jo026384o.

Titanium(IV) benzylidenes bearing a masked oxygen or nitrogen nucleophile in the ortho position were generated from thioacetals, using low-valent titanocene complex, Cp2Ti[P(OEt)3]2. Methylene acetal, alkyl ether, silyl ether, fluoro, tertiary amino, and N-alkyl, N-benzyl, N-prenyl, and N-silyl tert-butyl carbamate...

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Macleod C, McKiernan GJ, Guthrie EJ, et al. Synthesis of 2-substituted benzofurans and indoles using functionalized titanium benzylidene reagents on solid phase. J Org Chem. 2003;68(2):387-401doi: 10.1021/jo026384o.
Macleod, C., McKiernan, G. J., Guthrie, E. J., Farrugia, L. J., Hamprecht, D. W., Macritchie, J., & Hartley, R. C. (2003). Synthesis of 2-substituted benzofurans and indoles using functionalized titanium benzylidene reagents on solid phase. The Journal of organic chemistry, 68(2), 387-401. https://doi.org/10.1021/jo026384o
Macleod, Calum, et al. "Synthesis of 2-substituted benzofurans and indoles using functionalized titanium benzylidene reagents on solid phase." The Journal of organic chemistry vol. 68,2 (2003): 387-401. doi: https://doi.org/10.1021/jo026384o
Macleod C, McKiernan GJ, Guthrie EJ, Farrugia LJ, Hamprecht DW, Macritchie J, Hartley RC. Synthesis of 2-substituted benzofurans and indoles using functionalized titanium benzylidene reagents on solid phase. J Org Chem. 2003 Jan 24;68(2):387-401. doi: 10.1021/jo026384o. PMID: 12530864.
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Efficient [3,3]-sigmatropic rearrangement accelerated by a trifluoroacetyl group: synthesis of benzofurans under mild conditions.

Organic & biomolecular chemistry

Miyata O, Takeda N, Morikami Y, Naito T.
PMID: 12929420
Org Biomol Chem. 2003 Jan 21;1(2):254-6. doi: 10.1039/b210059b.

The [3,3]-sigmatropic rearrangement took place smoothly during the course of trifluoroacetylation of O-phenyloxime at below room temperature to give the dihydrobenzofuran or benzofuran as a result of concomitant cyclization.

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Miyata O, Takeda N, Morikami Y, et al. Efficient [3,3]-sigmatropic rearrangement accelerated by a trifluoroacetyl group: synthesis of benzofurans under mild conditions. Org Biomol Chem. 2003;1(2):254-6doi: 10.1039/b210059b.
Miyata, O., Takeda, N., Morikami, Y., & Naito, T. (2003). Efficient [3,3]-sigmatropic rearrangement accelerated by a trifluoroacetyl group: synthesis of benzofurans under mild conditions. Organic & biomolecular chemistry, 1(2), 254-6. https://doi.org/10.1039/b210059b
Miyata, Okiko, et al. "Efficient [3,3]-sigmatropic rearrangement accelerated by a trifluoroacetyl group: synthesis of benzofurans under mild conditions." Organic & biomolecular chemistry vol. 1,2 (2003): 254-6. doi: https://doi.org/10.1039/b210059b
Miyata O, Takeda N, Morikami Y, Naito T. Efficient [3,3]-sigmatropic rearrangement accelerated by a trifluoroacetyl group: synthesis of benzofurans under mild conditions. Org Biomol Chem. 2003 Jan 21;1(2):254-6. doi: 10.1039/b210059b. PMID: 12929420.
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A highly selective cascade approach to diverse aromatic ring systems from simple aromatic aldehydes and propiolates.

Organic letters

Wang YG, Cui SL, Lin XF.
PMID: 16524313
Org Lett. 2006 Mar 16;8(6):1241-4. doi: 10.1021/ol060143b.

[reaction: see text] A new triethylamine-catalyzed cascade reaction of aromatic aldehydes with propiolates has been developed. This serial multi-bond-forming process furnishes diverse polycyclic aromatic hydrocarbons, including naphthalenes, phenanthrenes, benzofurans, and 2,3,9,9a-tetrahydronaphtha[2,3-b]furans. The chemical outcome of the process depends on...

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Wang YG, Cui SL, Lin XF. A highly selective cascade approach to diverse aromatic ring systems from simple aromatic aldehydes and propiolates. Org Lett. 2006;8(6):1241-4doi: 10.1021/ol060143b.
Wang, Y. G., Cui, S. L., & Lin, X. F. (2006). A highly selective cascade approach to diverse aromatic ring systems from simple aromatic aldehydes and propiolates. Organic letters, 8(6), 1241-4. https://doi.org/10.1021/ol060143b
Wang, Yan-Guang, et al. "A highly selective cascade approach to diverse aromatic ring systems from simple aromatic aldehydes and propiolates." Organic letters vol. 8,6 (2006): 1241-4. doi: https://doi.org/10.1021/ol060143b
Wang YG, Cui SL, Lin XF. A highly selective cascade approach to diverse aromatic ring systems from simple aromatic aldehydes and propiolates. Org Lett. 2006 Mar 16;8(6):1241-4. doi: 10.1021/ol060143b. PMID: 16524313.
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Sequential homobimetallic catalysis: an unprecedented tandem Pd(0)-catalysed deprotection - Pd(II)-catalysed heterocyclisation reaction leading to benzofurans.

Chemical communications (Cambridge, England)

Gabriele B, Mancuso R, Salerno G, Veltri L.
PMID: 15724209
Chem Commun (Camb). 2005 Jan 14;(2):271-3. doi: 10.1039/b413240h. Epub 2004 Nov 12.

We report here the first example of "sequential homobimetallic catalysis": a transition metal catalyst with the metal in a certain oxidation state catalyses the deprotection of a functional group, which in situ undergoes a subsequent transformation catalysed by another...

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Gabriele B, Mancuso R, Salerno G, et al. Sequential homobimetallic catalysis: an unprecedented tandem Pd(0)-catalysed deprotection - Pd(II)-catalysed heterocyclisation reaction leading to benzofurans. Chem Commun (Camb). 2004;(2):271-3doi: 10.1039/b413240h.
Gabriele, B., Mancuso, R., Salerno, G., & Veltri, L. (2005). Sequential homobimetallic catalysis: an unprecedented tandem Pd(0)-catalysed deprotection - Pd(II)-catalysed heterocyclisation reaction leading to benzofurans. Chemical communications (Cambridge, England), (2), 271-3. https://doi.org/10.1039/b413240h
Gabriele, Bartolo, et al. "Sequential homobimetallic catalysis: an unprecedented tandem Pd(0)-catalysed deprotection - Pd(II)-catalysed heterocyclisation reaction leading to benzofurans." Chemical communications (Cambridge, England) vol. ,2 (2005): 271-3. doi: https://doi.org/10.1039/b413240h
Gabriele B, Mancuso R, Salerno G, Veltri L. Sequential homobimetallic catalysis: an unprecedented tandem Pd(0)-catalysed deprotection - Pd(II)-catalysed heterocyclisation reaction leading to benzofurans. Chem Commun (Camb). 2005 Jan 14;(2):271-3. doi: 10.1039/b413240h. Epub 2004 Nov 12. PMID: 15724209.
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Phosphazene base-catalyzed intramolecular cyclization for efficient synthesis of benzofurans via carbon-carbon bond formation.

Chemical communications (Cambridge, England)

Kanazawa C, Goto K, Terada M.
PMID: 19707635
Chem Commun (Camb). 2009 Sep 21;(35):5248-50. doi: 10.1039/b913588j. Epub 2009 Aug 07.

An organic superbase, phosphazene P4-(t)Bu, functioned as an active catalyst for intramolecular cyclization of o-alkynylphenyl ethers via carbon-carbon bond formation to provide an efficient synthetic method for 2,3-disubstituted benzofurans derivatives under mild reaction conditions without the need for a...

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Kanazawa C, Goto K, Terada M. Phosphazene base-catalyzed intramolecular cyclization for efficient synthesis of benzofurans via carbon-carbon bond formation. Chem Commun (Camb). 2009;(35):5248-50doi: 10.1039/b913588j.
Kanazawa, C., Goto, K., & Terada, M. (2009). Phosphazene base-catalyzed intramolecular cyclization for efficient synthesis of benzofurans via carbon-carbon bond formation. Chemical communications (Cambridge, England), (35), 5248-50. https://doi.org/10.1039/b913588j
Kanazawa, Chikashi, et al. "Phosphazene base-catalyzed intramolecular cyclization for efficient synthesis of benzofurans via carbon-carbon bond formation." Chemical communications (Cambridge, England) vol. ,35 (2009): 5248-50. doi: https://doi.org/10.1039/b913588j
Kanazawa C, Goto K, Terada M. Phosphazene base-catalyzed intramolecular cyclization for efficient synthesis of benzofurans via carbon-carbon bond formation. Chem Commun (Camb). 2009 Sep 21;(35):5248-50. doi: 10.1039/b913588j. Epub 2009 Aug 07. PMID: 19707635.
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Showing 1 to 12 of 210 entries