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Nickel-Mediated Asymmetric Allylic Alkylation between Nitroallylic Acetates and Acyl Imidazoles.

Organic letters

Wang J, Wang P, Wang L, Li D, Wang K, Wang Y, Zhu H, Yang D, Wang R.
PMID: 28862455
Org Lett. 2017 Sep 15;19(18):4826-4829. doi: 10.1021/acs.orglett.7b02264. Epub 2017 Sep 01.

A nickel-mediated asymmetric allylic alkylation reaction between imidazole-modified ketones and nitroallylic acetates is presented. This reaction is catalyzed by a simple chiral diamine-nickel catalyst under mild conditions and leads to a series of novel enantioenriched α-allylic adducts in moderate...

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Wang J, Wang P, Wang L, et al. Nickel-Mediated Asymmetric Allylic Alkylation between Nitroallylic Acetates and Acyl Imidazoles. Org Lett. 2017;19(18):4826-4829doi: 10.1021/acs.orglett.7b02264.
Wang, J., Wang, P., Wang, L., Li, D., Wang, K., Wang, Y., Zhu, H., Yang, D., & Wang, R. (2017). Nickel-Mediated Asymmetric Allylic Alkylation between Nitroallylic Acetates and Acyl Imidazoles. Organic letters, 19(18), 4826-4829. https://doi.org/10.1021/acs.orglett.7b02264
Wang, Jie, et al. "Nickel-Mediated Asymmetric Allylic Alkylation between Nitroallylic Acetates and Acyl Imidazoles." Organic letters vol. 19,18 (2017): 4826-4829. doi: https://doi.org/10.1021/acs.orglett.7b02264
Wang J, Wang P, Wang L, Li D, Wang K, Wang Y, Zhu H, Yang D, Wang R. Nickel-Mediated Asymmetric Allylic Alkylation between Nitroallylic Acetates and Acyl Imidazoles. Org Lett. 2017 Sep 15;19(18):4826-4829. doi: 10.1021/acs.orglett.7b02264. Epub 2017 Sep 01. PMID: 28862455.
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Asymmetric dual catalysis via fragmentation of a single rhodium precursor complex.

Chemical communications (Cambridge, England)

Song L, Gong L, Meggers E.
PMID: 27231188
Chem Commun (Camb). 2016 Jun 08;52(49):7699-702. doi: 10.1039/c6cc03157a.

A strategy for dual transition metal catalysis and organocatalysis is reported via the in situ disintegration of a single rhodium complex. The hereby generated chiral Lewis acid and l-β-phenylalanine synergistically catalyze the Michael addition of α,α-disubstituted aldehydes to α,β-unsaturated...

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Song L, Gong L, Meggers E. Asymmetric dual catalysis via fragmentation of a single rhodium precursor complex. Chem Commun (Camb). 2016;52(49):7699-702doi: 10.1039/c6cc03157a.
Song, L., Gong, L., & Meggers, E. (2016). Asymmetric dual catalysis via fragmentation of a single rhodium precursor complex. Chemical communications (Cambridge, England), 52(49), 7699-702. https://doi.org/10.1039/c6cc03157a
Song, Liangliang, et al. "Asymmetric dual catalysis via fragmentation of a single rhodium precursor complex." Chemical communications (Cambridge, England) vol. 52,49 (2016): 7699-702. doi: https://doi.org/10.1039/c6cc03157a
Song L, Gong L, Meggers E. Asymmetric dual catalysis via fragmentation of a single rhodium precursor complex. Chem Commun (Camb). 2016 Jun 08;52(49):7699-702. doi: 10.1039/c6cc03157a. PMID: 27231188.
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One-Pot Synthesis of Polysubstituted Imidazoles via Sequential Staudinger/aza-Wittig/Ag(I)-Catalyzed Cyclization/Isomerization.

The Journal of organic chemistry

Xiong J, Wei X, Liu ZM, Ding MW.
PMID: 29148765
J Org Chem. 2017 Dec 15;82(24):13735-13739. doi: 10.1021/acs.joc.7b02606. Epub 2017 Nov 28.

A new one-pot preparation of polysubstituted imidazoles by a Staudinger/aza-Wittig/Ag(I)-catalyzed cyclization/isomerization has been developed. The easily accessible propargylazide derivatives reacted with triphenylphosphine, isocyanates, and amines sequentially to produce the fully substituted imidazoles in good overall yields in the presence...

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Xiong J, Wei X, Liu ZM, et al. One-Pot Synthesis of Polysubstituted Imidazoles via Sequential Staudinger/aza-Wittig/Ag(I)-Catalyzed Cyclization/Isomerization. J Org Chem. 2017;82(24):13735-13739doi: 10.1021/acs.joc.7b02606.
Xiong, J., Wei, X., Liu, Z. M., & Ding, M. W. (2017). One-Pot Synthesis of Polysubstituted Imidazoles via Sequential Staudinger/aza-Wittig/Ag(I)-Catalyzed Cyclization/Isomerization. The Journal of organic chemistry, 82(24), 13735-13739. https://doi.org/10.1021/acs.joc.7b02606
Xiong, Jun, et al. "One-Pot Synthesis of Polysubstituted Imidazoles via Sequential Staudinger/aza-Wittig/Ag(I)-Catalyzed Cyclization/Isomerization." The Journal of organic chemistry vol. 82,24 (2017): 13735-13739. doi: https://doi.org/10.1021/acs.joc.7b02606
Xiong J, Wei X, Liu ZM, Ding MW. One-Pot Synthesis of Polysubstituted Imidazoles via Sequential Staudinger/aza-Wittig/Ag(I)-Catalyzed Cyclization/Isomerization. J Org Chem. 2017 Dec 15;82(24):13735-13739. doi: 10.1021/acs.joc.7b02606. Epub 2017 Nov 28. PMID: 29148765.
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Catalytic Asymmetric Michael Reaction of 5H-Oxazol-4-Ones with α,β-Unsaturated Acyl Imidazoles.

Chemistry (Weinheim an der Bergstrasse, Germany)

Zhang B, Han F, Wang L, Li D, Yang D, Yang X, Yang J, Li X, Zhao D, Wang R.
PMID: 26439322
Chemistry. 2015 Nov 23;21(48):17234-8. doi: 10.1002/chem.201503105. Epub 2015 Oct 14.

The asymmetric Michael reaction between 5H-oxazol-4-ones and α,β-unsaturated acyl imidazoles is reported. A novel 2-benzo[b]thiophenyl-modified chiral ProPhenol species is synthesized and used as a ligand, leading to good enantioselectivities in this asymmetric conjugate addition reaction. Furthermore, the introduction of...

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Zhang B, Han F, Wang L, et al. Catalytic Asymmetric Michael Reaction of 5H-Oxazol-4-Ones with α,β-Unsaturated Acyl Imidazoles. Chemistry. 2015;21(48):17234-8doi: 10.1002/chem.201503105.
Zhang, B., Han, F., Wang, L., Li, D., Yang, D., Yang, X., Yang, J., Li, X., Zhao, D., & Wang, R. (2015). Catalytic Asymmetric Michael Reaction of 5H-Oxazol-4-Ones with α,β-Unsaturated Acyl Imidazoles. Chemistry (Weinheim an der Bergstrasse, Germany), 21(48), 17234-8. https://doi.org/10.1002/chem.201503105
Zhang, Bangzhi, et al. "Catalytic Asymmetric Michael Reaction of 5H-Oxazol-4-Ones with α,β-Unsaturated Acyl Imidazoles." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,48 (2015): 17234-8. doi: https://doi.org/10.1002/chem.201503105
Zhang B, Han F, Wang L, Li D, Yang D, Yang X, Yang J, Li X, Zhao D, Wang R. Catalytic Asymmetric Michael Reaction of 5H-Oxazol-4-Ones with α,β-Unsaturated Acyl Imidazoles. Chemistry. 2015 Nov 23;21(48):17234-8. doi: 10.1002/chem.201503105. Epub 2015 Oct 14. PMID: 26439322.
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Dual Roles of Methyl Ketones in Radziszewski-Type Reaction: Formal [2 + 1 + 1 + 1] Synthesis of 1,2,5-Trisubstituted Imidazoles.

Organic letters

Zhang J, Gao Q, Wu X, Geng X, Wu YD, Wu A.
PMID: 26985658
Org Lett. 2016 Apr 01;18(7):1686-9. doi: 10.1021/acs.orglett.6b00607. Epub 2016 Mar 17.

A highly efficient molecular iodine mediated Radziszewski-type reaction of methyl ketones, anilines, and tosylmethyl isocyanide has been developed. This protocol represents an elegant molecular fragment assembly of imidazoles via a formal [2 + 1 + 1 + 1] annulation....

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Zhang J, Gao Q, Wu X, et al. Dual Roles of Methyl Ketones in Radziszewski-Type Reaction: Formal [2 + 1 + 1 + 1] Synthesis of 1,2,5-Trisubstituted Imidazoles. Org Lett. 2016;18(7):1686-9doi: 10.1021/acs.orglett.6b00607.
Zhang, J., Gao, Q., Wu, X., Geng, X., Wu, Y. D., & Wu, A. (2016). Dual Roles of Methyl Ketones in Radziszewski-Type Reaction: Formal [2 + 1 + 1 + 1] Synthesis of 1,2,5-Trisubstituted Imidazoles. Organic letters, 18(7), 1686-9. https://doi.org/10.1021/acs.orglett.6b00607
Zhang, Jingjing, et al. "Dual Roles of Methyl Ketones in Radziszewski-Type Reaction: Formal [2 + 1 + 1 + 1] Synthesis of 1,2,5-Trisubstituted Imidazoles." Organic letters vol. 18,7 (2016): 1686-9. doi: https://doi.org/10.1021/acs.orglett.6b00607
Zhang J, Gao Q, Wu X, Geng X, Wu YD, Wu A. Dual Roles of Methyl Ketones in Radziszewski-Type Reaction: Formal [2 + 1 + 1 + 1] Synthesis of 1,2,5-Trisubstituted Imidazoles. Org Lett. 2016 Apr 01;18(7):1686-9. doi: 10.1021/acs.orglett.6b00607. Epub 2016 Mar 17. PMID: 26985658.
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Spectroscopic and thermal studies on 2- and 4-phenyl-1H-imidazoles.

Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy

Hachuła B, Polasz A, Książek M, Kusz J, Starczewska O, Pisarski W.
PMID: 28460318
Spectrochim Acta A Mol Biomol Spectrosc. 2017 Aug 05;183:378-386. doi: 10.1016/j.saa.2017.04.062. Epub 2017 Apr 24.

The polarized IR spectra of isotopically neat and isotopically substituted monocrystalline samples of 2-phenyl-1H-imidazole (2PI) and 4-phenyl-1H-imidazole (4PI) were recorded at two temperatures of 293 K and 77 K. The room-temperature ATR-FTIR and Raman spectra of 2PI and two...

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Hachuła B, Polasz A, Książek M, et al. Spectroscopic and thermal studies on 2- and 4-phenyl-1H-imidazoles. Spectrochim Acta A Mol Biomol Spectrosc. 2017;183:378-386doi: 10.1016/j.saa.2017.04.062.
Hachuła, B., Polasz, A., Książek, M., Kusz, J., Starczewska, O., & Pisarski, W. (2017). Spectroscopic and thermal studies on 2- and 4-phenyl-1H-imidazoles. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 183378-386. https://doi.org/10.1016/j.saa.2017.04.062
Hachuła, Barbara, et al. "Spectroscopic and thermal studies on 2- and 4-phenyl-1H-imidazoles." Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy vol. 183 (2017): 378-386. doi: https://doi.org/10.1016/j.saa.2017.04.062
Hachuła B, Polasz A, Książek M, Kusz J, Starczewska O, Pisarski W. Spectroscopic and thermal studies on 2- and 4-phenyl-1H-imidazoles. Spectrochim Acta A Mol Biomol Spectrosc. 2017 Aug 05;183:378-386. doi: 10.1016/j.saa.2017.04.062. Epub 2017 Apr 24. PMID: 28460318.
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Correction to "Divergent Reactivity of Amino Acid Alkyl Ester Hydrochlorides with 2-Oxoaldehydes: Role of Selenium Dioxide To Promote Regioselective Synthesis of Imidazoles".

Organic letters

Padala AK, Kumar RR, Athimoolam S, Ahmed QN.
PMID: 26883871
Org Lett. 2016 Mar 04;18(5):1217-8. doi: 10.1021/acs.orglett.6b00353. Epub 2016 Feb 17.

No abstract available.

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Padala AK, Kumar RR, Athimoolam S, et al. Correction to "Divergent Reactivity of Amino Acid Alkyl Ester Hydrochlorides with 2-Oxoaldehydes: Role of Selenium Dioxide To Promote Regioselective Synthesis of Imidazoles". Org Lett. 2016;18(5):1217-8doi: 10.1021/acs.orglett.6b00353.
Padala, A. K., Kumar, R. R., Athimoolam, S., & Ahmed, Q. N. (2016). Correction to "Divergent Reactivity of Amino Acid Alkyl Ester Hydrochlorides with 2-Oxoaldehydes: Role of Selenium Dioxide To Promote Regioselective Synthesis of Imidazoles". Organic letters, 18(5), 1217-8. https://doi.org/10.1021/acs.orglett.6b00353
Padala, Anil K, et al. "Correction to "Divergent Reactivity of Amino Acid Alkyl Ester Hydrochlorides with 2-Oxoaldehydes: Role of Selenium Dioxide To Promote Regioselective Synthesis of Imidazoles"." Organic letters vol. 18,5 (2016): 1217-8. doi: https://doi.org/10.1021/acs.orglett.6b00353
Padala AK, Kumar RR, Athimoolam S, Ahmed QN. Correction to "Divergent Reactivity of Amino Acid Alkyl Ester Hydrochlorides with 2-Oxoaldehydes: Role of Selenium Dioxide To Promote Regioselective Synthesis of Imidazoles". Org Lett. 2016 Mar 04;18(5):1217-8. doi: 10.1021/acs.orglett.6b00353. Epub 2016 Feb 17. PMID: 26883871.
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Ionic crosslinking of imidazolium functionalized poly(aryl ether ketone) by sulfonated poly(ether ether ketone) for anion exchange membranes.

Journal of colloid and interface science

Xu Y, Ye N, Zhang D, Yang J, He R.
PMID: 28301829
J Colloid Interface Sci. 2017 Jul 01;497:333-342. doi: 10.1016/j.jcis.2017.03.033. Epub 2017 Mar 06.

Two N3-substituted imidazoles 1,2-dimethylimidazole and 1-butyl-2-methylimidazole were chosen to functionalize poly(aryl ether ketone), respectively. The generated imidazolium cations could electrostatically react with sulfonate ions of the sulfonated poly(ether ether ketone) forming the ionic crosslinking structure of the membranes. The...

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Xu Y, Ye N, Zhang D, et al. Ionic crosslinking of imidazolium functionalized poly(aryl ether ketone) by sulfonated poly(ether ether ketone) for anion exchange membranes. J Colloid Interface Sci. 2017;497:333-342doi: 10.1016/j.jcis.2017.03.033.
Xu, Y., Ye, N., Zhang, D., Yang, J., & He, R. (2017). Ionic crosslinking of imidazolium functionalized poly(aryl ether ketone) by sulfonated poly(ether ether ketone) for anion exchange membranes. Journal of colloid and interface science, 497333-342. https://doi.org/10.1016/j.jcis.2017.03.033
Xu, Yixin, et al. "Ionic crosslinking of imidazolium functionalized poly(aryl ether ketone) by sulfonated poly(ether ether ketone) for anion exchange membranes." Journal of colloid and interface science vol. 497 (2017): 333-342. doi: https://doi.org/10.1016/j.jcis.2017.03.033
Xu Y, Ye N, Zhang D, Yang J, He R. Ionic crosslinking of imidazolium functionalized poly(aryl ether ketone) by sulfonated poly(ether ether ketone) for anion exchange membranes. J Colloid Interface Sci. 2017 Jul 01;497:333-342. doi: 10.1016/j.jcis.2017.03.033. Epub 2017 Mar 06. PMID: 28301829.
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Light-Induced Direct Arylation in the Solid Crystalline State as a Strategy Towards π-Expanded Imidazoles.

Chemistry, an Asian journal

Skonieczny K, Gryko DT.
PMID: 27452918
Chem Asian J. 2016 Sep 20;11(18):2513-7. doi: 10.1002/asia.201600752. Epub 2016 Aug 25.

π-Expanded imidazoles bearing the 2-iodophenyl substituent at position 2 undergo direct photoinduced intramolecular arylation in the solid, crystalline state leading to large non-planar heterocycles. An analogous reaction employing 2-bromophenyl and 2-chlorophenyl substituents is considerably slower. Such processes have never...

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Skonieczny K, Gryko DT. Light-Induced Direct Arylation in the Solid Crystalline State as a Strategy Towards π-Expanded Imidazoles. Chem Asian J. 2016;11(18):2513-7doi: 10.1002/asia.201600752.
Skonieczny, K., & Gryko, D. T. (2016). Light-Induced Direct Arylation in the Solid Crystalline State as a Strategy Towards π-Expanded Imidazoles. Chemistry, an Asian journal, 11(18), 2513-7. https://doi.org/10.1002/asia.201600752
Skonieczny, Kamil, and Gryko, Daniel T. "Light-Induced Direct Arylation in the Solid Crystalline State as a Strategy Towards π-Expanded Imidazoles." Chemistry, an Asian journal vol. 11,18 (2016): 2513-7. doi: https://doi.org/10.1002/asia.201600752
Skonieczny K, Gryko DT. Light-Induced Direct Arylation in the Solid Crystalline State as a Strategy Towards π-Expanded Imidazoles. Chem Asian J. 2016 Sep 20;11(18):2513-7. doi: 10.1002/asia.201600752. Epub 2016 Aug 25. PMID: 27452918.
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Photochemical Conversion of Phenanthro[9,10-d]imidazoles into π-Expanded Heterocycles.

The Journal of organic chemistry

Skonieczny K, Gryko DT.
PMID: 25938658
J Org Chem. 2015 Jun 05;80(11):5753-63. doi: 10.1021/acs.joc.5b00714. Epub 2015 May 15.

We discovered that phenanthro[9,10-d]imidazoles bearing a 2-halogenoaryl substituent at position 2 undergo swift photochemically driven direct arylation, leading to barely known phenanthro[9',10':4,5]imidazo[1,2-f]phenanthridines. The reaction is high-yielding, and it does not require any sensitizer or base. The discovered process is...

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Skonieczny K, Gryko DT. Photochemical Conversion of Phenanthro[9,10-d]imidazoles into π-Expanded Heterocycles. J Org Chem. 2015;80(11):5753-63doi: 10.1021/acs.joc.5b00714.
Skonieczny, K., & Gryko, D. T. (2015). Photochemical Conversion of Phenanthro[9,10-d]imidazoles into π-Expanded Heterocycles. The Journal of organic chemistry, 80(11), 5753-63. https://doi.org/10.1021/acs.joc.5b00714
Skonieczny, Kamil, and Gryko, Daniel T. "Photochemical Conversion of Phenanthro[9,10-d]imidazoles into π-Expanded Heterocycles." The Journal of organic chemistry vol. 80,11 (2015): 5753-63. doi: https://doi.org/10.1021/acs.joc.5b00714
Skonieczny K, Gryko DT. Photochemical Conversion of Phenanthro[9,10-d]imidazoles into π-Expanded Heterocycles. J Org Chem. 2015 Jun 05;80(11):5753-63. doi: 10.1021/acs.joc.5b00714. Epub 2015 May 15. PMID: 25938658.
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A concise synthesis of highly substituted imidazoles via copper-mediated oxidative C-H functionalization.

Tetrahedron letters

Pandya AN, Agrawal DK.
PMID: 24882889
Tetrahedron Lett. 2014 Mar 05;55(10):1835-1838. doi: 10.1016/j.tetlet.2014.01.136.

We herein report a simple and concise route for the synthesis of highly substituted imidazole derivatives via copper-mediated oxidative C-H functionalization in good to high yields. The advantage of the reaction lies in its mild reaction conditions and readily...

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Pandya AN, Agrawal DK. A concise synthesis of highly substituted imidazoles via copper-mediated oxidative C-H functionalization. Tetrahedron Lett. 2014;55(10):1835-1838doi: 10.1016/j.tetlet.2014.01.136.
Pandya, A. N., & Agrawal, D. K. (2014). A concise synthesis of highly substituted imidazoles via copper-mediated oxidative C-H functionalization. Tetrahedron letters, 55(10), 1835-1838. https://doi.org/10.1016/j.tetlet.2014.01.136
Pandya, Amit N, and Agrawal, Devendra K. "A concise synthesis of highly substituted imidazoles via copper-mediated oxidative C-H functionalization." Tetrahedron letters vol. 55,10 (2014): 1835-1838. doi: https://doi.org/10.1016/j.tetlet.2014.01.136
Pandya AN, Agrawal DK. A concise synthesis of highly substituted imidazoles via copper-mediated oxidative C-H functionalization. Tetrahedron Lett. 2014 Mar 05;55(10):1835-1838. doi: 10.1016/j.tetlet.2014.01.136. PMID: 24882889; PMCID: PMC4034134.
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4(5)-Aryl-2-C-glucopyranosyl-imidazoles as New Nanomolar Glucose Analogue Inhibitors of Glycogen Phosphorylase.

ACS medicinal chemistry letters

Bokor É, Kun S, Docsa T, Gergely P, Somsák L.
PMID: 26713107
ACS Med Chem Lett. 2015 Oct 19;6(12):1215-9. doi: 10.1021/acsmedchemlett.5b00361. eCollection 2015 Dec 10.

Inhibition of glycogen phosphorylases may lead to pharmacological treatments of diseases in which glycogen metabolism plays an important role: first of all in diabetes, but also in cardiovascular and tumorous disorders. C-(β-d-Glucopyranosyl) isoxazole, pyrazole, thiazole, and imidazole type compounds...

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Bokor É, Kun S, Docsa T, et al. 4(5)-Aryl-2-C-glucopyranosyl-imidazoles as New Nanomolar Glucose Analogue Inhibitors of Glycogen Phosphorylase. ACS Med Chem Lett. 2015;6(12):1215-9doi: 10.1021/acsmedchemlett.5b00361.
Bokor, �. �., Kun, S., Docsa, T., Gergely, P., & Somsák, L. (2015). 4(5)-Aryl-2-C-glucopyranosyl-imidazoles as New Nanomolar Glucose Analogue Inhibitors of Glycogen Phosphorylase. ACS medicinal chemistry letters, 6(12), 1215-9. https://doi.org/10.1021/acsmedchemlett.5b00361
Bokor, Éva, et al. "4(5)-Aryl-2-C-glucopyranosyl-imidazoles as New Nanomolar Glucose Analogue Inhibitors of Glycogen Phosphorylase." ACS medicinal chemistry letters vol. 6,12 (2015): 1215-9. doi: https://doi.org/10.1021/acsmedchemlett.5b00361
Bokor É, Kun S, Docsa T, Gergely P, Somsák L. 4(5)-Aryl-2-C-glucopyranosyl-imidazoles as New Nanomolar Glucose Analogue Inhibitors of Glycogen Phosphorylase. ACS Med Chem Lett. 2015 Oct 19;6(12):1215-9. doi: 10.1021/acsmedchemlett.5b00361. eCollection 2015 Dec 10. PMID: 26713107; PMCID: PMC4677374.
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