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You searched for +publisher:"York University" +contributor:("Orellana Garcia, Josue Arturo"). Showing records 1 – 3 of 3 total matches.

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York University

1. Nikolaev, Andrei. Synthesis and Reactivity of Umpolung Reagents Through Transition Metal Catalysis.

Degree: PhD, Chemistry, 2019, York University

The cyclopropanol-derived palladium-homoenolates have previously been exploited as a unique class of cross-coupling partners in our group. The major advantage of using cyclopropanols as the cross-coupling partners is the fact that the functional group content is preserved. Specifically, cyclopropanol forms the corresponding -functionalized carbonyl product which can be used for further transformations. We developed an efficient method towards the synthesis of quinoline derivatives with broad functional group tolerance using series of cyclopropanols and ortho-bromoanilines as the cross-coupling partners in the presence of a palladium-catalyst. A deuterium labeling study revealed that a second equivalent of ortho-bromoaniline is the terminal oxidant in this reaction. Considering the importance of aza-aromatic heterocycles in biologically active drug molecules, there is a continuous demand for rapid and benign methods towards their functionalization. Hence, we wanted to exploit a transition-metal catalyzed free-radical ring opening reaction of cyclopropanols towards rapid and efficient functionalization of pyridine derivatives. We development a silver-catalyzed direct functionalization of heteroaromatic compounds with a well-defined silver catalyst. Through this study, we gained strong evidence which suggests that silver-pyridine complexes are the catalytically active species for free-radical ring-opening of the cyclopropanol. Acylsilanes are classic umpolung reagents with broad synthetic applications. Specifically, acylsilanes undergo polarity inversion at the carbonyl-carbon via the 1,2-Brook rearrangement with a concomitant reaction with an electrophile. Unfortunately, synthetic methods for acylsilanes often involve many steps and harsh conditions. We explored a mild synthetic method for the preparation of ,-unsaturated acylsilanes via perrhenate-catalyzed Meyer-Schuster rearrangement of 3-silyl propargylic alcohols. Advisors/Committee Members: Orellana Garcia, Josue Arturo (advisor).

Subjects/Keywords: Chemistry; Organic Chemistry; Organic Synthesis; Catalysis; Organometallics; Umpolung

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APA (6th Edition):

Nikolaev, A. (2019). Synthesis and Reactivity of Umpolung Reagents Through Transition Metal Catalysis. (Doctoral Dissertation). York University. Retrieved from http://hdl.handle.net/10315/35919

Chicago Manual of Style (16th Edition):

Nikolaev, Andrei. “Synthesis and Reactivity of Umpolung Reagents Through Transition Metal Catalysis.” 2019. Doctoral Dissertation, York University. Accessed October 20, 2020. http://hdl.handle.net/10315/35919.

MLA Handbook (7th Edition):

Nikolaev, Andrei. “Synthesis and Reactivity of Umpolung Reagents Through Transition Metal Catalysis.” 2019. Web. 20 Oct 2020.

Vancouver:

Nikolaev A. Synthesis and Reactivity of Umpolung Reagents Through Transition Metal Catalysis. [Internet] [Doctoral dissertation]. York University; 2019. [cited 2020 Oct 20]. Available from: http://hdl.handle.net/10315/35919.

Council of Science Editors:

Nikolaev A. Synthesis and Reactivity of Umpolung Reagents Through Transition Metal Catalysis. [Doctoral Dissertation]. York University; 2019. Available from: http://hdl.handle.net/10315/35919


York University

2. Rasheed, Faizan. Mild and Selective Palladium-Catalyzed Pyridylic Allylation of 4-Alkylpyridines.

Degree: MSc -MS, Chemistry, 2020, York University

Pyridines and related heterocycles enjoy widespread occurrence in biologically relevant natural products and drug-like molecules. Therefore, new methods that facilitate their synthesis and incorporation into drug-like structures will likely have a significant impact on the drug development process. This is especially true when these methods accomplish selective functionalization and allow a broad functional group tolerance. Reported herein is a new strategy for the selective allylation of 4-alkylpyridine derivatives. Our methodology exploits well-established alkylidene dihydropyridine intermediates as substrates for a Pd-catalyzed decarboxylative allylation reaction, which installs a synthetically versatile allyl group at the 4-pyridylic position. The use of a weak base and the absence of a Lewis acid in our method enables the allylation of 4-alkylpyridines with exceptional functional group tolerance. Moreover, the compatibility of the proposed pyridylic allylation strategy extends beyond simple 4-alkylpyridines to more sophisticated 3- and 4-disubstituted pyridines. Advisors/Committee Members: Orellana Garcia, Josue Arturo (advisor).

Subjects/Keywords: Organic chemistry; Transition metal; Palladium; Pyridine; Cross coupling; Organometallic chemistry; Drug discovery

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6th Edition):

Rasheed, F. (2020). Mild and Selective Palladium-Catalyzed Pyridylic Allylation of 4-Alkylpyridines. (Masters Thesis). York University. Retrieved from http://hdl.handle.net/10315/37663

Chicago Manual of Style (16th Edition):

Rasheed, Faizan. “Mild and Selective Palladium-Catalyzed Pyridylic Allylation of 4-Alkylpyridines.” 2020. Masters Thesis, York University. Accessed October 20, 2020. http://hdl.handle.net/10315/37663.

MLA Handbook (7th Edition):

Rasheed, Faizan. “Mild and Selective Palladium-Catalyzed Pyridylic Allylation of 4-Alkylpyridines.” 2020. Web. 20 Oct 2020.

Vancouver:

Rasheed F. Mild and Selective Palladium-Catalyzed Pyridylic Allylation of 4-Alkylpyridines. [Internet] [Masters thesis]. York University; 2020. [cited 2020 Oct 20]. Available from: http://hdl.handle.net/10315/37663.

Council of Science Editors:

Rasheed F. Mild and Selective Palladium-Catalyzed Pyridylic Allylation of 4-Alkylpyridines. [Masters Thesis]. York University; 2020. Available from: http://hdl.handle.net/10315/37663


York University

3. Zhang, Minhao. The Total Synthesis of () 7-HDHA.

Degree: MSc -MS, Chemistry, 2020, York University

Fatty acid () 7-HDHA was recently identified as an endogenous ligand for PPAR/ receptors by one of our collaborators Dr. Henry Krause group. While this discovery is promising in understanding PPARs mechanism of effects and related diseases (Alzheimers disease, cerebral ischemia, retina inflammation, etc.), the study of 7-HDHA in relation to PPARs has been hampered by the high cost and limited supply of 7-HDHA. The total synthesis of 7-HDHA was attempted using four different strategies, and finally achieved in 11 steps in the longest reaction sequence, starting from commercially available (triisopropylsilyl)acetylene and 2-pentyn-1-ol. The overall yield of this synthesis was 12%. This concise route mainly relies on the one-step generation of three Z-double bonds with the semi-hydrogenation catalyst P2-Nickel, and a late-stage semi-hydrogenation with Zn(Cu/Ag) reagent. The completion of this synthesis will now provide large quantities of 7-HDHA quickly, and thus enable extensive studies of PPAR 7-HDHA interaction. Advisors/Committee Members: Orellana Garcia, Josue Arturo (advisor).

Subjects/Keywords: Molecular chemistry; 7-HDHA; Fatty acid; Total synthesis; ppar; P2-Nickel; Natural product; rcm; Ring-closing metathesis; Hydroxyl docosahexaenoic acid; Semi-hydrogenation; Sonogashira; Claisen rearrangement

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6th Edition):

Zhang, M. (2020). The Total Synthesis of () 7-HDHA. (Masters Thesis). York University. Retrieved from https://yorkspace.library.yorku.ca/xmlui/handle/10315/37385

Chicago Manual of Style (16th Edition):

Zhang, Minhao. “The Total Synthesis of () 7-HDHA.” 2020. Masters Thesis, York University. Accessed October 20, 2020. https://yorkspace.library.yorku.ca/xmlui/handle/10315/37385.

MLA Handbook (7th Edition):

Zhang, Minhao. “The Total Synthesis of () 7-HDHA.” 2020. Web. 20 Oct 2020.

Vancouver:

Zhang M. The Total Synthesis of () 7-HDHA. [Internet] [Masters thesis]. York University; 2020. [cited 2020 Oct 20]. Available from: https://yorkspace.library.yorku.ca/xmlui/handle/10315/37385.

Council of Science Editors:

Zhang M. The Total Synthesis of () 7-HDHA. [Masters Thesis]. York University; 2020. Available from: https://yorkspace.library.yorku.ca/xmlui/handle/10315/37385

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