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Rhodium(III)-catalyzed redox-neutral coupling of N-phenoxyacetamides and alkynes with tunable selectivity.

Angewandte Chemie (International ed. in English)

Liu G, Shen Y, Zhou Z, Lu X.
PMID: 23616372
Angew Chem Int Ed Engl. 2013 Jun 03;52(23):6033-7. doi: 10.1002/anie.201300881. Epub 2013 Apr 24.

Give it a tweak: A novel oxidizing directing group was developed for a rhodium(III)-catalyzed CH functionalization of N-phenoxyacetamides with alkynes. A small change in the reaction conditions leads to either ortho-hydroxyphenyl-substituted enamides or cyclization to deliver benzofurans with high...

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Liu G, Shen Y, Zhou Z, et al. Rhodium(III)-catalyzed redox-neutral coupling of N-phenoxyacetamides and alkynes with tunable selectivity. Angew Chem Int Ed Engl. 2013;52(23):6033-7doi: 10.1002/anie.201300881.
Liu, G., Shen, Y., Zhou, Z., & Lu, X. (2013). Rhodium(III)-catalyzed redox-neutral coupling of N-phenoxyacetamides and alkynes with tunable selectivity. Angewandte Chemie (International ed. in English), 52(23), 6033-7. https://doi.org/10.1002/anie.201300881
Liu, Guixia, et al. "Rhodium(III)-catalyzed redox-neutral coupling of N-phenoxyacetamides and alkynes with tunable selectivity." Angewandte Chemie (International ed. in English) vol. 52,23 (2013): 6033-7. doi: https://doi.org/10.1002/anie.201300881
Liu G, Shen Y, Zhou Z, Lu X. Rhodium(III)-catalyzed redox-neutral coupling of N-phenoxyacetamides and alkynes with tunable selectivity. Angew Chem Int Ed Engl. 2013 Jun 03;52(23):6033-7. doi: 10.1002/anie.201300881. Epub 2013 Apr 24. PMID: 23616372.
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Synthesis of indenofurans, benzofurans and spiro-lactones via Hauser-Kraus annulation involving 1,6-addition of phthalide to quinone methides.

Organic & biomolecular chemistry

Basu P, Satam N, Namboothiri INN.
PMID: 32662476
Org Biomol Chem. 2020 Jul 29;18(29):5677-5687. doi: 10.1039/d0ob01115k.

An unprecedented reactivity of 3-sulfonylphthalide with 2-hydroxyaryl-p-quinone methides (HQMs) is reported here. A cascade of reactions starting with 1,6-addition and Dieckmann cyclization produced a diverse array of indenofurans and benzofurans in high yields, depending on the amount of base...

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Basu P, Satam N, Namboothiri INN. Synthesis of indenofurans, benzofurans and spiro-lactones via Hauser-Kraus annulation involving 1,6-addition of phthalide to quinone methides. Org Biomol Chem. 2020;18(29):5677-5687doi: 10.1039/d0ob01115k.
Basu, P., Satam, N., & Namboothiri, I. N. N. (2020). Synthesis of indenofurans, benzofurans and spiro-lactones via Hauser-Kraus annulation involving 1,6-addition of phthalide to quinone methides. Organic & biomolecular chemistry, 18(29), 5677-5687. https://doi.org/10.1039/d0ob01115k
Basu, Pallabita, et al. "Synthesis of indenofurans, benzofurans and spiro-lactones via Hauser-Kraus annulation involving 1,6-addition of phthalide to quinone methides." Organic & biomolecular chemistry vol. 18,29 (2020): 5677-5687. doi: https://doi.org/10.1039/d0ob01115k
Basu P, Satam N, Namboothiri INN. Synthesis of indenofurans, benzofurans and spiro-lactones via Hauser-Kraus annulation involving 1,6-addition of phthalide to quinone methides. Org Biomol Chem. 2020 Jul 29;18(29):5677-5687. doi: 10.1039/d0ob01115k. PMID: 32662476.
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Iodocyclization in Aqueous Media and Supramolecular Reaction Control Using Water-Soluble Hosts.

ACS omega

Bokoskie T, Cunningham C, Kornman C, Kesharwani T, Pattabiraman M.
PMID: 31681890
ACS Omega. 2019 Oct 17;4(18):17830-17836. doi: 10.1021/acsomega.9b02466. eCollection 2019 Oct 29.

Iodocyclization of 2-alkynylanisoles is an efficient route for synthesizing substituted benzofurans. Reaction efficiency with copper(II) sulfate and sodium iodide in an aqueous slurry under mild conditions is a manifold higher than in organic solvents. Water-soluble hosts of the cyclodextrin...

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Bokoskie T, Cunningham C, Kornman C, et al. Iodocyclization in Aqueous Media and Supramolecular Reaction Control Using Water-Soluble Hosts. ACS Omega. 2019;4(18):17830-17836doi: 10.1021/acsomega.9b02466.
Bokoskie, T., Cunningham, C., Kornman, C., Kesharwani, T., & Pattabiraman, M. (2019). Iodocyclization in Aqueous Media and Supramolecular Reaction Control Using Water-Soluble Hosts. ACS omega, 4(18), 17830-17836. https://doi.org/10.1021/acsomega.9b02466
Bokoskie, Treyvon, et al. "Iodocyclization in Aqueous Media and Supramolecular Reaction Control Using Water-Soluble Hosts." ACS omega vol. 4,18 (2019): 17830-17836. doi: https://doi.org/10.1021/acsomega.9b02466
Bokoskie T, Cunningham C, Kornman C, Kesharwani T, Pattabiraman M. Iodocyclization in Aqueous Media and Supramolecular Reaction Control Using Water-Soluble Hosts. ACS Omega. 2019 Oct 17;4(18):17830-17836. doi: 10.1021/acsomega.9b02466. eCollection 2019 Oct 29. PMID: 31681890; PMCID: PMC6822118.
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N-Phenoxyamides as Multitasking Reagents: Base-Controlled Selective Construction of Benzofurans or Dihydrobenzofuro[2,3- d]oxazoles.

The Journal of organic chemistry

Li M, Wang JH, Li W, Lin CD, Zhang LB, Wen LR.
PMID: 31190539
J Org Chem. 2019 Jul 05;84(13):8523-8530. doi: 10.1021/acs.joc.9b00858. Epub 2019 Jun 24.

An efficient method to selectively construct benzofuran and dihydrobenzofuro[2,3- d]oxazole derivatives has been successfully established by means of base-controlled cyclization of N-phenoxyamides with 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1 H)-one (TIPS-EBX). N-phenoxyamides as multitasking reagents have triggered two different cascade reaction sequences. This is...

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Li M, Wang JH, Li W, et al. N-Phenoxyamides as Multitasking Reagents: Base-Controlled Selective Construction of Benzofurans or Dihydrobenzofuro[2,3- d]oxazoles. J Org Chem. 2019;84(13):8523-8530doi: 10.1021/acs.joc.9b00858.
Li, M., Wang, J. H., Li, W., Lin, C. D., Zhang, L. B., & Wen, L. R. (2019). N-Phenoxyamides as Multitasking Reagents: Base-Controlled Selective Construction of Benzofurans or Dihydrobenzofuro[2,3- d]oxazoles. The Journal of organic chemistry, 84(13), 8523-8530. https://doi.org/10.1021/acs.joc.9b00858
Li, Ming, et al. "N-Phenoxyamides as Multitasking Reagents: Base-Controlled Selective Construction of Benzofurans or Dihydrobenzofuro[2,3- d]oxazoles." The Journal of organic chemistry vol. 84,13 (2019): 8523-8530. doi: https://doi.org/10.1021/acs.joc.9b00858
Li M, Wang JH, Li W, Lin CD, Zhang LB, Wen LR. N-Phenoxyamides as Multitasking Reagents: Base-Controlled Selective Construction of Benzofurans or Dihydrobenzofuro[2,3- d]oxazoles. J Org Chem. 2019 Jul 05;84(13):8523-8530. doi: 10.1021/acs.joc.9b00858. Epub 2019 Jun 24. PMID: 31190539.
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A Base-Mediated Approach Towards Dihydrofuro[2,3-b]Benzofurans from 2-Nitrobenzofurans and 1,3-Dicarbonyls.

Chemistry, an Asian journal

Singh G, Pandey R, Kurup AS, Anand RV.
PMID: 33788982
Chem Asian J. 2021 May 17;16(10):1271-1279. doi: 10.1002/asia.202100184. Epub 2021 Apr 27.

A straight-forward approach for the synthesis of a dihydrofuro[2,3-b]benzofuran derivatives has been achieved through a base-mediated Michael addition of 1,3-dicarbonyls to 2-nitrobenzofurans followed by intramolecular cyclization. A variety of 1,3-dicarbonyls, including cyclic as well as trifluoromethylated ones, have been...

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Singh G, Pandey R, Kurup AS, et al. A Base-Mediated Approach Towards Dihydrofuro[2,3-b]Benzofurans from 2-Nitrobenzofurans and 1,3-Dicarbonyls. Chem Asian J. 2021;16(10):1271-1279doi: 10.1002/asia.202100184.
Singh, G., Pandey, R., Kurup, A. S., & Anand, R. V. (2021). A Base-Mediated Approach Towards Dihydrofuro[2,3-b]Benzofurans from 2-Nitrobenzofurans and 1,3-Dicarbonyls. Chemistry, an Asian journal, 16(10), 1271-1279. https://doi.org/10.1002/asia.202100184
Singh, Gurdeep, et al. "A Base-Mediated Approach Towards Dihydrofuro[2,3-b]Benzofurans from 2-Nitrobenzofurans and 1,3-Dicarbonyls." Chemistry, an Asian journal vol. 16,10 (2021): 1271-1279. doi: https://doi.org/10.1002/asia.202100184
Singh G, Pandey R, Kurup AS, Anand RV. A Base-Mediated Approach Towards Dihydrofuro[2,3-b]Benzofurans from 2-Nitrobenzofurans and 1,3-Dicarbonyls. Chem Asian J. 2021 May 17;16(10):1271-1279. doi: 10.1002/asia.202100184. Epub 2021 Apr 27. PMID: 33788982.
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Phosphine-Catalyzed Chemoselective Reduction/Elimination/Wittig Sequence for Synthesis of Functionalized 3-Alkenyl Benzofurans.

Organic letters

Liou YC, Wang HW, Edukondalu A, Lin W.
PMID: 33821660
Org Lett. 2021 Apr 16;23(8):3064-3069. doi: 10.1021/acs.orglett.1c00737. Epub 2021 Apr 06.

An efficient protocol for the construction of functionalized 3-alkenyl benzofurans is demonstrated under metal-free conditions using catalytic amount of phosphine proceeding an intramolecular Wittig reaction. This one-pot reaction initiated by the phospha-Michael addition of phosphine to

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Liou YC, Wang HW, Edukondalu A, et al. Phosphine-Catalyzed Chemoselective Reduction/Elimination/Wittig Sequence for Synthesis of Functionalized 3-Alkenyl Benzofurans. Org Lett. 2021;23(8):3064-3069doi: 10.1021/acs.orglett.1c00737.
Liou, Y. C., Wang, H. W., Edukondalu, A., & Lin, W. (2021). Phosphine-Catalyzed Chemoselective Reduction/Elimination/Wittig Sequence for Synthesis of Functionalized 3-Alkenyl Benzofurans. Organic letters, 23(8), 3064-3069. https://doi.org/10.1021/acs.orglett.1c00737
Liou, Yan-Cheng, et al. "Phosphine-Catalyzed Chemoselective Reduction/Elimination/Wittig Sequence for Synthesis of Functionalized 3-Alkenyl Benzofurans." Organic letters vol. 23,8 (2021): 3064-3069. doi: https://doi.org/10.1021/acs.orglett.1c00737
Liou YC, Wang HW, Edukondalu A, Lin W. Phosphine-Catalyzed Chemoselective Reduction/Elimination/Wittig Sequence for Synthesis of Functionalized 3-Alkenyl Benzofurans. Org Lett. 2021 Apr 16;23(8):3064-3069. doi: 10.1021/acs.orglett.1c00737. Epub 2021 Apr 06. PMID: 33821660.
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Copper-Catalyzed Direct Perfluoroalkylation of Heteroarenes.

Chemistry (Weinheim an der Bergstrasse, Germany)

Baguia H, Evano G.
PMID: 34842313
Chemistry. 2021 Nov 29; doi: 10.1002/chem.202103599. Epub 2021 Nov 29.

An efficient and broadly applicable process is reported for the copper-catalyzed direct perfluoroalkylation of C-H bonds in heteroarenes with commercially available perfluoroalkyl iodides. This reaction is based on a simple combination of copper(I) iodide and 1,10-phenanthroline enabling the easy...

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Baguia H, Evano G. Copper-Catalyzed Direct Perfluoroalkylation of Heteroarenes. Chemistry. 2021;doi: 10.1002/chem.202103599.
Baguia, H., & Evano, G. (2021). Copper-Catalyzed Direct Perfluoroalkylation of Heteroarenes. Chemistry (Weinheim an der Bergstrasse, Germany), . https://doi.org/10.1002/chem.202103599
Baguia, Hajar, and Evano, Gwilherm. "Copper-Catalyzed Direct Perfluoroalkylation of Heteroarenes." Chemistry (Weinheim an der Bergstrasse, Germany) vol. (2021). doi: https://doi.org/10.1002/chem.202103599
Baguia H, Evano G. Copper-Catalyzed Direct Perfluoroalkylation of Heteroarenes. Chemistry. 2021 Nov 29; doi: 10.1002/chem.202103599. Epub 2021 Nov 29. PMID: 34842313.
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ortho-Oxygenative 1,2-Difunctionalization of Diarylalkynes under Merged Gold/Organophotoredox Relay Catalysis.

Chemistry, an Asian journal

Sancheti SP, Akram MO, Roy R, Bedi V, Kundu S, Patil NT.
PMID: 31589800
Chem Asian J. 2019 Dec 13;14(24):4601-4606. doi: 10.1002/asia.201901275. Epub 2019 Oct 30.

Reported herein is an ortho-oxygenative 1,2-difunctionalization of diarylalkynes under merged gold/organophotoredox catalysis to access highly functionalized 2-(2-hydroxyaryl)-2-alkoxy-1-arylethan-1-ones. Detailed mechanistic studies suggested a relay process, initiating with gold-catalyzed hydroalkoxylation of alkynes, to generate enol-ether followed by a key formal [4+2]-cycloaddition...

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Sancheti SP, Akram MO, Roy R, et al. ortho-Oxygenative 1,2-Difunctionalization of Diarylalkynes under Merged Gold/Organophotoredox Relay Catalysis. Chem Asian J. 2019;14(24):4601-4606doi: 10.1002/asia.201901275.
Sancheti, S. P., Akram, M. O., Roy, R., Bedi, V., Kundu, S., & Patil, N. T. (2019). ortho-Oxygenative 1,2-Difunctionalization of Diarylalkynes under Merged Gold/Organophotoredox Relay Catalysis. Chemistry, an Asian journal, 14(24), 4601-4606. https://doi.org/10.1002/asia.201901275
Sancheti, Shashank P, et al. "ortho-Oxygenative 1,2-Difunctionalization of Diarylalkynes under Merged Gold/Organophotoredox Relay Catalysis." Chemistry, an Asian journal vol. 14,24 (2019): 4601-4606. doi: https://doi.org/10.1002/asia.201901275
Sancheti SP, Akram MO, Roy R, Bedi V, Kundu S, Patil NT. ortho-Oxygenative 1,2-Difunctionalization of Diarylalkynes under Merged Gold/Organophotoredox Relay Catalysis. Chem Asian J. 2019 Dec 13;14(24):4601-4606. doi: 10.1002/asia.201901275. Epub 2019 Oct 30. PMID: 31589800.
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Tandem Ullmann-Goldberg Cross-Coupling/Cyclopalladation-Reductive Elimination Reactions and Related Sequences Leading to Polyfunctionalized Benzofurans, Indoles, and Phthalanes.

Organic letters

Khan F, Fatima M, Shirzaei M, Vo Y, Amarasiri M, Banwell MG, Ma C, Ward JS, Gardiner MG.
PMID: 31364356
Org Lett. 2019 Aug 16;21(16):6342-6346. doi: 10.1021/acs.orglett.9b02235. Epub 2019 Jul 31.

On exposure to a combination of Cu[I]- and Pd[0]-based catalysts, compounds such as

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Khan F, Fatima M, Shirzaei M, et al. Tandem Ullmann-Goldberg Cross-Coupling/Cyclopalladation-Reductive Elimination Reactions and Related Sequences Leading to Polyfunctionalized Benzofurans, Indoles, and Phthalanes. Org Lett. 2019;21(16):6342-6346doi: 10.1021/acs.orglett.9b02235.
Khan, F., Fatima, M., Shirzaei, M., Vo, Y., Amarasiri, M., Banwell, M. G., Ma, C., Ward, J. S., & Gardiner, M. G. (2019). Tandem Ullmann-Goldberg Cross-Coupling/Cyclopalladation-Reductive Elimination Reactions and Related Sequences Leading to Polyfunctionalized Benzofurans, Indoles, and Phthalanes. Organic letters, 21(16), 6342-6346. https://doi.org/10.1021/acs.orglett.9b02235
Khan, Faiyaz, et al. "Tandem Ullmann-Goldberg Cross-Coupling/Cyclopalladation-Reductive Elimination Reactions and Related Sequences Leading to Polyfunctionalized Benzofurans, Indoles, and Phthalanes." Organic letters vol. 21,16 (2019): 6342-6346. doi: https://doi.org/10.1021/acs.orglett.9b02235
Khan F, Fatima M, Shirzaei M, Vo Y, Amarasiri M, Banwell MG, Ma C, Ward JS, Gardiner MG. Tandem Ullmann-Goldberg Cross-Coupling/Cyclopalladation-Reductive Elimination Reactions and Related Sequences Leading to Polyfunctionalized Benzofurans, Indoles, and Phthalanes. Org Lett. 2019 Aug 16;21(16):6342-6346. doi: 10.1021/acs.orglett.9b02235. Epub 2019 Jul 31. PMID: 31364356.
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Tandem addition/cyclization for synthesis of 2-aroyl benzofurans and 2-aroyl indoles by carbopalladation of nitriles.

Organic & biomolecular chemistry

Gong J, Hu K, Shao Y, Li R, Zhang Y, Hu M, Chen J.
PMID: 31850443
Org Biomol Chem. 2020 Jan 22;18(3):488-494. doi: 10.1039/c9ob02408e.

The first example of the palladium-catalyzed tandem addition/cyclization of 2-(2-acylphenoxy)acetonitriles with arylboronic acids has been developed, providing a new strategy for the synthesis of 2-aroyl benzofurans with excellent chemoselectivity and wide functional group compatibility. Preliminary mechanistic experiments indicate that...

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Gong J, Hu K, Shao Y, et al. Tandem addition/cyclization for synthesis of 2-aroyl benzofurans and 2-aroyl indoles by carbopalladation of nitriles. Org Biomol Chem. 2020;18(3):488-494doi: 10.1039/c9ob02408e.
Gong, J., Hu, K., Shao, Y., Li, R., Zhang, Y., Hu, M., & Chen, J. (2020). Tandem addition/cyclization for synthesis of 2-aroyl benzofurans and 2-aroyl indoles by carbopalladation of nitriles. Organic & biomolecular chemistry, 18(3), 488-494. https://doi.org/10.1039/c9ob02408e
Gong, Julin, et al. "Tandem addition/cyclization for synthesis of 2-aroyl benzofurans and 2-aroyl indoles by carbopalladation of nitriles." Organic & biomolecular chemistry vol. 18,3 (2020): 488-494. doi: https://doi.org/10.1039/c9ob02408e
Gong J, Hu K, Shao Y, Li R, Zhang Y, Hu M, Chen J. Tandem addition/cyclization for synthesis of 2-aroyl benzofurans and 2-aroyl indoles by carbopalladation of nitriles. Org Biomol Chem. 2020 Jan 22;18(3):488-494. doi: 10.1039/c9ob02408e. PMID: 31850443.
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The Benzofurans of Isocoma wrightii. Structure and Stereochemistry.

Journal of natural products

Zalkow LH, Ekpo BA, Gelbaum LT, Harris RN, Keinan E, Novak JR, Ramming CT, Van Derveer D.
PMID: 27802393
J Nat Prod. 1979 Mar;42(2):203-219. doi: 10.1021/np50002a012.

No abstract available.

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Zalkow LH, Ekpo BA, Gelbaum LT, et al. The Benzofurans of Isocoma wrightii. Structure and Stereochemistry. J Nat Prod. 1979;42(2):203-219doi: 10.1021/np50002a012.
Zalkow, L. H., Ekpo, B. A., Gelbaum, L. T., Harris, R. N., Keinan, E., Novak, J. R., Ramming, C. T., & Van Derveer, D. (1979). The Benzofurans of Isocoma wrightii. Structure and Stereochemistry. Journal of natural products, 42(2), 203-219. https://doi.org/10.1021/np50002a012
Zalkow, L H, et al. "The Benzofurans of Isocoma wrightii. Structure and Stereochemistry." Journal of natural products vol. 42,2 (1979): 203-219. doi: https://doi.org/10.1021/np50002a012
Zalkow LH, Ekpo BA, Gelbaum LT, Harris RN, Keinan E, Novak JR, Ramming CT, Van Derveer D. The Benzofurans of Isocoma wrightii. Structure and Stereochemistry. J Nat Prod. 1979 Mar;42(2):203-219. doi: 10.1021/np50002a012. PMID: 27802393.
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Therapeutic potential of naturally occurring benzofuran derivatives and hybrids of benzofurans with other pharmacophores as antibacterial agents.

Current topics in medicinal chemistry

Xu Z, Xu D, Zhou W, Zhang X.
PMID: 34809548
Curr Top Med Chem. 2021 Nov 22; doi: 10.2174/1568026621666211122162439. Epub 2021 Nov 22.

Gram-positive and Gram-negative pathogens are able to evade the host immune system, persist within the human host, and lead to severe disease and even death. At present, bacterial infections are one of the leading causes of morbidity and mortality...

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Xu Z, Xu D, Zhou W, et al. Therapeutic potential of naturally occurring benzofuran derivatives and hybrids of benzofurans with other pharmacophores as antibacterial agents. Curr Top Med Chem. 2021;doi: 10.2174/1568026621666211122162439.
Xu, Z., Xu, D., Zhou, W., & Zhang, X. (2021). Therapeutic potential of naturally occurring benzofuran derivatives and hybrids of benzofurans with other pharmacophores as antibacterial agents. Current topics in medicinal chemistry, . https://doi.org/10.2174/1568026621666211122162439
Xu, Zhi, et al. "Therapeutic potential of naturally occurring benzofuran derivatives and hybrids of benzofurans with other pharmacophores as antibacterial agents." Current topics in medicinal chemistry vol. (2021). doi: https://doi.org/10.2174/1568026621666211122162439
Xu Z, Xu D, Zhou W, Zhang X. Therapeutic potential of naturally occurring benzofuran derivatives and hybrids of benzofurans with other pharmacophores as antibacterial agents. Curr Top Med Chem. 2021 Nov 22; doi: 10.2174/1568026621666211122162439. Epub 2021 Nov 22. PMID: 34809548.
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Showing 25 to 36 of 210 entries