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Pd-Catalyzed Intramolecular Cyclization via Direct C-H Addition to Nitriles: Skeletal Diverse Synthesis of Fused Polycyclic Indoles.

Organic letters

Wang TT, Zhao L, Zhang YJ, Liao WW.
PMID: 27626643
Org Lett. 2016 Oct 07;18(19):5002-5005. doi: 10.1021/acs.orglett.6b02460. Epub 2016 Sep 14.

The first example of Pd-catalyzed intramolecular C-H addition of indoles bearing cyanohydrin components at the C(3), C(2), and N(1) positions to nitriles is described. A wide range of functionalized partially saturated carbazoles, tetrahydropyrido[1,2-a]indole, and carbazoles can be prepared in...

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Wang TT, Zhao L, Zhang YJ, et al. Pd-Catalyzed Intramolecular Cyclization via Direct C-H Addition to Nitriles: Skeletal Diverse Synthesis of Fused Polycyclic Indoles. Org Lett. 2016;18(19):5002-5005doi: 10.1021/acs.orglett.6b02460.
Wang, T. T., Zhao, L., Zhang, Y. J., & Liao, W. W. (2016). Pd-Catalyzed Intramolecular Cyclization via Direct C-H Addition to Nitriles: Skeletal Diverse Synthesis of Fused Polycyclic Indoles. Organic letters, 18(19), 5002-5005. https://doi.org/10.1021/acs.orglett.6b02460
Wang, Ting-Ting, et al. "Pd-Catalyzed Intramolecular Cyclization via Direct C-H Addition to Nitriles: Skeletal Diverse Synthesis of Fused Polycyclic Indoles." Organic letters vol. 18,19 (2016): 5002-5005. doi: https://doi.org/10.1021/acs.orglett.6b02460
Wang TT, Zhao L, Zhang YJ, Liao WW. Pd-Catalyzed Intramolecular Cyclization via Direct C-H Addition to Nitriles: Skeletal Diverse Synthesis of Fused Polycyclic Indoles. Org Lett. 2016 Oct 07;18(19):5002-5005. doi: 10.1021/acs.orglett.6b02460. Epub 2016 Sep 14. PMID: 27626643.
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Studies on [PtCl2 ]- or [AuCl]-catalyzed cyclization of 1-(Indol-2-yl)-2,3-allenols: the effects of water/steric hindrance and 1,2-migration selectivity.

Chemistry (Weinheim an der Bergstrasse, Germany)

Qiu Y, Fu C, Zhang X, Ma S.
PMID: 25056816
Chemistry. 2014 Aug 11;20(33):10314-22. doi: 10.1002/chem.201402423. Epub 2014 Jul 23.

The [PtCl2 ]- or [AuCl]-catalyzed reaction of 1-(indol-2-yl)-2,3-allenols occurred smoothly at room temperature to afford a series of poly-substituted carbazoles efficiently. Compared with the [PtCl2 ]-catalyzed process, the [AuCl]-catalyzed reaction represents a significant advance in terms of the scope...

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Qiu Y, Fu C, Zhang X, et al. Studies on [PtCl2 ]- or [AuCl]-catalyzed cyclization of 1-(Indol-2-yl)-2,3-allenols: the effects of water/steric hindrance and 1,2-migration selectivity. Chemistry. 2014;20(33):10314-22doi: 10.1002/chem.201402423.
Qiu, Y., Fu, C., Zhang, X., & Ma, S. (2014). Studies on [PtCl2 ]- or [AuCl]-catalyzed cyclization of 1-(Indol-2-yl)-2,3-allenols: the effects of water/steric hindrance and 1,2-migration selectivity. Chemistry (Weinheim an der Bergstrasse, Germany), 20(33), 10314-22. https://doi.org/10.1002/chem.201402423
Qiu, Youai, et al. "Studies on [PtCl2 ]- or [AuCl]-catalyzed cyclization of 1-(Indol-2-yl)-2,3-allenols: the effects of water/steric hindrance and 1,2-migration selectivity." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 20,33 (2014): 10314-22. doi: https://doi.org/10.1002/chem.201402423
Qiu Y, Fu C, Zhang X, Ma S. Studies on [PtCl2 ]- or [AuCl]-catalyzed cyclization of 1-(Indol-2-yl)-2,3-allenols: the effects of water/steric hindrance and 1,2-migration selectivity. Chemistry. 2014 Aug 11;20(33):10314-22. doi: 10.1002/chem.201402423. Epub 2014 Jul 23. PMID: 25056816.
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Access to Benzo[a]carbazoles and Indeno[1,2-c]quinolines by a Gold(I)-Catalyzed Tunable Domino Cyclization of Difunctional 1,2-Diphenylethynes.

Organic letters

Peng X, Zhu L, Hou Y, Pang Y, Li Y, Fu J, Yang L, Lin B, Liu Y, Cheng M.
PMID: 28598637
Org Lett. 2017 Jul 07;19(13):3402-3405. doi: 10.1021/acs.orglett.7b01358. Epub 2017 Jun 09.

The cyclization order of the difunctional 1,2-diphenylethynes was precisely tuned under the catalysis of gold by changing the nitrogen substitution of the substrates, leading to the facile preparation of benzo[a]carbazole and indeno[1,2-c]quinoline derivatives. The mechanisms of these domino cyclizations...

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Peng X, Zhu L, Hou Y, et al. Access to Benzo[a]carbazoles and Indeno[1,2-c]quinolines by a Gold(I)-Catalyzed Tunable Domino Cyclization of Difunctional 1,2-Diphenylethynes. Org Lett. 2017;19(13):3402-3405doi: 10.1021/acs.orglett.7b01358.
Peng, X., Zhu, L., Hou, Y., Pang, Y., Li, Y., Fu, J., Yang, L., Lin, B., Liu, Y., & Cheng, M. (2017). Access to Benzo[a]carbazoles and Indeno[1,2-c]quinolines by a Gold(I)-Catalyzed Tunable Domino Cyclization of Difunctional 1,2-Diphenylethynes. Organic letters, 19(13), 3402-3405. https://doi.org/10.1021/acs.orglett.7b01358
Peng, Xiaoshi, et al. "Access to Benzo[a]carbazoles and Indeno[1,2-c]quinolines by a Gold(I)-Catalyzed Tunable Domino Cyclization of Difunctional 1,2-Diphenylethynes." Organic letters vol. 19,13 (2017): 3402-3405. doi: https://doi.org/10.1021/acs.orglett.7b01358
Peng X, Zhu L, Hou Y, Pang Y, Li Y, Fu J, Yang L, Lin B, Liu Y, Cheng M. Access to Benzo[a]carbazoles and Indeno[1,2-c]quinolines by a Gold(I)-Catalyzed Tunable Domino Cyclization of Difunctional 1,2-Diphenylethynes. Org Lett. 2017 Jul 07;19(13):3402-3405. doi: 10.1021/acs.orglett.7b01358. Epub 2017 Jun 09. PMID: 28598637.
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An unprecedented benzannulation of oxindoles with enalcarbenoids: a regioselective approach to functionalized carbazoles.

Chemical communications (Cambridge, England)

Rathore KS, Lad BS, Chennamsetti H, Katukojvala S.
PMID: 26992045
Chem Commun (Camb). 2016 Apr 30;52(34):5812-5. doi: 10.1039/c5cc10637k. Epub 2016 Mar 18.

A novel Rh(ii)/Brønsted acid catalyzed tandem benzannulation of oxindoles with enaldiazo carbonyls led to the formation of valuable 1-hydroxy-2-acylcarbazoles. This reaction is proposed to involve a formal insertion of a rhodium enalcarbenoid into an oxindole sp(2) C-O bond, an...

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Rathore KS, Lad BS, Chennamsetti H, et al. An unprecedented benzannulation of oxindoles with enalcarbenoids: a regioselective approach to functionalized carbazoles. Chem Commun (Camb). 2016;52(34):5812-5doi: 10.1039/c5cc10637k.
Rathore, K. S., Lad, B. S., Chennamsetti, H., & Katukojvala, S. (2016). An unprecedented benzannulation of oxindoles with enalcarbenoids: a regioselective approach to functionalized carbazoles. Chemical communications (Cambridge, England), 52(34), 5812-5. https://doi.org/10.1039/c5cc10637k
Rathore, Kuldeep Singh, et al. "An unprecedented benzannulation of oxindoles with enalcarbenoids: a regioselective approach to functionalized carbazoles." Chemical communications (Cambridge, England) vol. 52,34 (2016): 5812-5. doi: https://doi.org/10.1039/c5cc10637k
Rathore KS, Lad BS, Chennamsetti H, Katukojvala S. An unprecedented benzannulation of oxindoles with enalcarbenoids: a regioselective approach to functionalized carbazoles. Chem Commun (Camb). 2016 Apr 30;52(34):5812-5. doi: 10.1039/c5cc10637k. Epub 2016 Mar 18. PMID: 26992045.
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Brønsted Acid-Mediated Cycloaromatization of 1H-Indol-2-yl Propargyl Benzoates to 7H-Benzo[c]carbazoles.

Chemistry, an Asian journal

Tan JK, Mathiew M, Nayak S, Chan PWH.
PMID: 28608646
Chem Asian J. 2017 Jul 04;12(13):1475-1479. doi: 10.1002/asia.201700419. Epub 2017 Jun 13.

A synthetic method for the efficient assembly of benzo[c]carbazole derivatives that relies on silica gel-activated benzoic acid-mediated cycloaromatization of 1H-indol-2-yl propargyl benzoates under atmospheric conditions is described. Robust with a variety of substitution patterns tolerated, the reaction provides a...

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Tan JK, Mathiew M, Nayak S, et al. Brønsted Acid-Mediated Cycloaromatization of 1H-Indol-2-yl Propargyl Benzoates to 7H-Benzo[c]carbazoles. Chem Asian J. 2017;12(13):1475-1479doi: 10.1002/asia.201700419.
Tan, J. K., Mathiew, M., Nayak, S., & Chan, P. W. H. (2017). Brønsted Acid-Mediated Cycloaromatization of 1H-Indol-2-yl Propargyl Benzoates to 7H-Benzo[c]carbazoles. Chemistry, an Asian journal, 12(13), 1475-1479. https://doi.org/10.1002/asia.201700419
Tan, Javey Khiapeng, et al. "Brønsted Acid-Mediated Cycloaromatization of 1H-Indol-2-yl Propargyl Benzoates to 7H-Benzo[c]carbazoles." Chemistry, an Asian journal vol. 12,13 (2017): 1475-1479. doi: https://doi.org/10.1002/asia.201700419
Tan JK, Mathiew M, Nayak S, Chan PWH. Brønsted Acid-Mediated Cycloaromatization of 1H-Indol-2-yl Propargyl Benzoates to 7H-Benzo[c]carbazoles. Chem Asian J. 2017 Jul 04;12(13):1475-1479. doi: 10.1002/asia.201700419. Epub 2017 Jun 13. PMID: 28608646.
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Multifunctional Tricarbazolo Triazolophane Macrocycles: One-Pot Preparation, Anion Binding, and Hierarchical Self-Organization of Multilayers.

Chemistry (Weinheim an der Bergstrasse, Germany)

Lee S, Hirsch BE, Liu Y, Dobscha JR, Burke DW, Tait SL, Flood AH.
PMID: 26593327
Chemistry. 2016 Jan 11;22(2):560-9. doi: 10.1002/chem.201503161. Epub 2015 Nov 23.

Programming the synthesis and self-assembly of molecules is a compelling strategy for the bottom-up fabrication of ordered materials. To this end, shape-persistent macrocycles were designed with alternating carbazoles and triazoles to program a one-pot synthesis and to bind large...

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Lee S, Hirsch BE, Liu Y, et al. Multifunctional Tricarbazolo Triazolophane Macrocycles: One-Pot Preparation, Anion Binding, and Hierarchical Self-Organization of Multilayers. Chemistry. 2015;22(2):560-9doi: 10.1002/chem.201503161.
Lee, S., Hirsch, B. E., Liu, Y., Dobscha, J. R., Burke, D. W., Tait, S. L., & Flood, A. H. (2016). Multifunctional Tricarbazolo Triazolophane Macrocycles: One-Pot Preparation, Anion Binding, and Hierarchical Self-Organization of Multilayers. Chemistry (Weinheim an der Bergstrasse, Germany), 22(2), 560-9. https://doi.org/10.1002/chem.201503161
Lee, Semin, et al. "Multifunctional Tricarbazolo Triazolophane Macrocycles: One-Pot Preparation, Anion Binding, and Hierarchical Self-Organization of Multilayers." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,2 (2016): 560-9. doi: https://doi.org/10.1002/chem.201503161
Lee S, Hirsch BE, Liu Y, Dobscha JR, Burke DW, Tait SL, Flood AH. Multifunctional Tricarbazolo Triazolophane Macrocycles: One-Pot Preparation, Anion Binding, and Hierarchical Self-Organization of Multilayers. Chemistry. 2016 Jan 11;22(2):560-9. doi: 10.1002/chem.201503161. Epub 2015 Nov 23. PMID: 26593327.
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Synthesis and properties of unsymmetrical azatrioxa[8]circulenes.

Organic & biomolecular chemistry

Plesner M, Hensel T, Nielsen BE, Kamounah FS, Brock-Nannestad T, Nielsen CB, Tortzen CG, Hammerich O, Pittelkow M.
PMID: 25925233
Org Biomol Chem. 2015 Jun 07;13(21):5937-43. doi: 10.1039/c5ob00676g.

Insights to the subtle reactivity patterns of hydroxy-substituted carbazoles allows the precise synthesis of unsymmetrical azatrioxa[8]circulenes by the reaction of N-benzyl-2,7-di-tert-butyl-3,6-dihydroxycarbazole with two different 1,4-benzoquinones in the presence of an oxidant (chloranil) and a Lewis acid (BF3OEt2). The unique...

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Plesner M, Hensel T, Nielsen BE, et al. Synthesis and properties of unsymmetrical azatrioxa[8]circulenes. Org Biomol Chem. 2015;13(21):5937-43doi: 10.1039/c5ob00676g.
Plesner, M., Hensel, T., Nielsen, B. E., Kamounah, F. S., Brock-Nannestad, T., Nielsen, C. B., Tortzen, C. G., Hammerich, O., & Pittelkow, M. (2015). Synthesis and properties of unsymmetrical azatrioxa[8]circulenes. Organic & biomolecular chemistry, 13(21), 5937-43. https://doi.org/10.1039/c5ob00676g
Plesner, Malene, et al. "Synthesis and properties of unsymmetrical azatrioxa[8]circulenes." Organic & biomolecular chemistry vol. 13,21 (2015): 5937-43. doi: https://doi.org/10.1039/c5ob00676g
Plesner M, Hensel T, Nielsen BE, Kamounah FS, Brock-Nannestad T, Nielsen CB, Tortzen CG, Hammerich O, Pittelkow M. Synthesis and properties of unsymmetrical azatrioxa[8]circulenes. Org Biomol Chem. 2015 Jun 07;13(21):5937-43. doi: 10.1039/c5ob00676g. PMID: 25925233.
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Metal-Free Dehydrogenative Diels-Alder Reactions of 2-Methyl-3-Alkylindoles with Dienophiles: Rapid Access to Tetrahydrocarbazoles, Carbazoles, and Heteroacenes.

Angewandte Chemie (International ed. in English)

Zhou L, Xu B, Zhang J.
PMID: 26096824
Angew Chem Int Ed Engl. 2015 Jul 27;54(31):9092-6. doi: 10.1002/anie.201503549. Epub 2015 Jun 10.

An unprecedented strategy for in situ generation of indole-based ortho-quinodimethanes (oQDMs) from 2-methyl-3-alkylmethylindoles by either a metal-free DDQ- or BQ-mediated dehydrogenative process was developed. These oQDMs were trapped by electron-deficient dienophiles to provide a facile approach to synthetically valuable...

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Zhou L, Xu B, Zhang J. Metal-Free Dehydrogenative Diels-Alder Reactions of 2-Methyl-3-Alkylindoles with Dienophiles: Rapid Access to Tetrahydrocarbazoles, Carbazoles, and Heteroacenes. Angew Chem Int Ed Engl. 2015;54(31):9092-6doi: 10.1002/anie.201503549.
Zhou, L., Xu, B., & Zhang, J. (2015). Metal-Free Dehydrogenative Diels-Alder Reactions of 2-Methyl-3-Alkylindoles with Dienophiles: Rapid Access to Tetrahydrocarbazoles, Carbazoles, and Heteroacenes. Angewandte Chemie (International ed. in English), 54(31), 9092-6. https://doi.org/10.1002/anie.201503549
Zhou, Liejin, et al. "Metal-Free Dehydrogenative Diels-Alder Reactions of 2-Methyl-3-Alkylindoles with Dienophiles: Rapid Access to Tetrahydrocarbazoles, Carbazoles, and Heteroacenes." Angewandte Chemie (International ed. in English) vol. 54,31 (2015): 9092-6. doi: https://doi.org/10.1002/anie.201503549
Zhou L, Xu B, Zhang J. Metal-Free Dehydrogenative Diels-Alder Reactions of 2-Methyl-3-Alkylindoles with Dienophiles: Rapid Access to Tetrahydrocarbazoles, Carbazoles, and Heteroacenes. Angew Chem Int Ed Engl. 2015 Jul 27;54(31):9092-6. doi: 10.1002/anie.201503549. Epub 2015 Jun 10. PMID: 26096824.
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Carbazole dendrimers as solution-processable thermally activated delayed-fluorescence materials.

Angewandte Chemie (International ed. in English)

Albrecht K, Matsuoka K, Fujita K, Yamamoto K.
PMID: 25753430
Angew Chem Int Ed Engl. 2015 May 04;54(19):5677-82. doi: 10.1002/anie.201500203. Epub 2015 Mar 05.

Recently, thermally activated delayed fluorescence (TADF) materials have received increasing attention as effective emitters for organic light-emitting diodes (OLEDs). However, most of them are usually employed as dopants in a host material. In this report, carbazole dendrimers with a...

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Albrecht K, Matsuoka K, Fujita K, et al. Carbazole dendrimers as solution-processable thermally activated delayed-fluorescence materials. Angew Chem Int Ed Engl. 2015;54(19):5677-82doi: 10.1002/anie.201500203.
Albrecht, K., Matsuoka, K., Fujita, K., & Yamamoto, K. (2015). Carbazole dendrimers as solution-processable thermally activated delayed-fluorescence materials. Angewandte Chemie (International ed. in English), 54(19), 5677-82. https://doi.org/10.1002/anie.201500203
Albrecht, Ken, et al. "Carbazole dendrimers as solution-processable thermally activated delayed-fluorescence materials." Angewandte Chemie (International ed. in English) vol. 54,19 (2015): 5677-82. doi: https://doi.org/10.1002/anie.201500203
Albrecht K, Matsuoka K, Fujita K, Yamamoto K. Carbazole dendrimers as solution-processable thermally activated delayed-fluorescence materials. Angew Chem Int Ed Engl. 2015 May 04;54(19):5677-82. doi: 10.1002/anie.201500203. Epub 2015 Mar 05. PMID: 25753430.
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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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Ir.

Chemistry, an Asian journal

Li SS, Xia YQ, Hu FZ, Liu CF, Su F, Dong L.
PMID: 27643614
Chem Asian J. 2016 Nov 22;11(22):3165-3168. doi: 10.1002/asia.201601197. Epub 2016 Oct 25.

A highly efficient Ir

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Li SS, Xia YQ, Hu FZ, et al. Ir. Chem Asian J. 2016;11(22):3165-3168doi: 10.1002/asia.201601197.
Li, S. S., Xia, Y. Q., Hu, F. Z., Liu, C. F., Su, F., & Dong, L. (2016). Ir. Chemistry, an Asian journal, 11(22), 3165-3168. https://doi.org/10.1002/asia.201601197
Li, Shuai-Shuai, et al. "Ir." Chemistry, an Asian journal vol. 11,22 (2016): 3165-3168. doi: https://doi.org/10.1002/asia.201601197
Li SS, Xia YQ, Hu FZ, Liu CF, Su F, Dong L. Ir. Chem Asian J. 2016 Nov 22;11(22):3165-3168. doi: 10.1002/asia.201601197. Epub 2016 Oct 25. PMID: 27643614.
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Indole-to-Carbazole Strategy for the Synthesis of Substituted Carbazoles under Metal-Free Conditions.

Organic letters

Chen S, Li Y, Ni P, Huang H, Deng GJ.
PMID: 27718584
Org Lett. 2016 Oct 21;18(20):5384-5387. doi: 10.1021/acs.orglett.6b02762. Epub 2016 Oct 10.

An efficient indole-to-carbazole strategy has been developed under metal-free conditions. This carbazole formation was highly promoted by NH

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Chen S, Li Y, Ni P, et al. Indole-to-Carbazole Strategy for the Synthesis of Substituted Carbazoles under Metal-Free Conditions. Org Lett. 2016;18(20):5384-5387doi: 10.1021/acs.orglett.6b02762.
Chen, S., Li, Y., Ni, P., Huang, H., & Deng, G. J. (2016). Indole-to-Carbazole Strategy for the Synthesis of Substituted Carbazoles under Metal-Free Conditions. Organic letters, 18(20), 5384-5387. https://doi.org/10.1021/acs.orglett.6b02762
Chen, Shanping, et al. "Indole-to-Carbazole Strategy for the Synthesis of Substituted Carbazoles under Metal-Free Conditions." Organic letters vol. 18,20 (2016): 5384-5387. doi: https://doi.org/10.1021/acs.orglett.6b02762
Chen S, Li Y, Ni P, Huang H, Deng GJ. Indole-to-Carbazole Strategy for the Synthesis of Substituted Carbazoles under Metal-Free Conditions. Org Lett. 2016 Oct 21;18(20):5384-5387. doi: 10.1021/acs.orglett.6b02762. Epub 2016 Oct 10. PMID: 27718584.
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Showing 1 to 12 of 368 entries