Nickel-catalyzed asymmetric cross-couplings of secondary alkyl electrophiles and photoinduced, copper-catalyzed C-N couplings
Thesis: Ph. D., Massachusetts Institute of Technology, Department of Chemistry, 2014.
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| Format: | Thesis |
| Language: | eng |
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Massachusetts Institute of Technology
2015
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| Online Access: | http://hdl.handle.net/1721.1/93033 |
| _version_ | 1826196261032689664 |
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| author | Choi, Junwon, Ph. D. Massachusetts Institute of Technology |
| author2 | Gregory C. Fu. |
| author_facet | Gregory C. Fu. Choi, Junwon, Ph. D. Massachusetts Institute of Technology |
| author_sort | Choi, Junwon, Ph. D. Massachusetts Institute of Technology |
| collection | MIT |
| description | Thesis: Ph. D., Massachusetts Institute of Technology, Department of Chemistry, 2014. |
| first_indexed | 2024-09-23T10:23:44Z |
| format | Thesis |
| id | mit-1721.1/93033 |
| institution | Massachusetts Institute of Technology |
| language | eng |
| last_indexed | 2024-09-23T10:23:44Z |
| publishDate | 2015 |
| publisher | Massachusetts Institute of Technology |
| record_format | dspace |
| spelling | mit-1721.1/930332019-04-12T15:56:53Z Nickel-catalyzed asymmetric cross-couplings of secondary alkyl electrophiles and photoinduced, copper-catalyzed C-N couplings Choi, Junwon, Ph. D. Massachusetts Institute of Technology Gregory C. Fu. Massachusetts Institute of Technology. Department of Chemistry. Massachusetts Institute of Technology. Department of Chemistry. Chemistry. Thesis: Ph. D., Massachusetts Institute of Technology, Department of Chemistry, 2014. Cataloged from PDF version of thesis. Vita. Includes bibliographical references. Chapter 1 describes the development of three nickel-catalyzed asymmetric Negishi cross-couplings of secondary alkyl electrophiles via a stereoconvergent process. In Section 1.1, asymmetric Negishi arylations and alkenylations of [alpha]-bromonitriles with arylzinc and alkenylzinc reagents are achieved using a nickel/bis(oxazoline) catalyst. Section 1.2 describes stereoconvergent cross-couplings of secondary unactivated alkyl electrophiles, specifically, Negishi arylations and alkenylations of [alpha]-bromosulfonamides and abromosulfones with arylzinc reagents and alkenylzirconium reagents, respectively. Section 1.3 details progress toward asymmetric cross-couplings between [alpha]-haloboronate esters and alkylzinc reagents using a nickel/diamine catalyst. Chapter 2 describes the development of photoinduced, copper-catalyzed C-N couplings between N-heterocycles and aryl halides. In particular, a variety of N-heterocycles, such as indoles, benzimidazoles, imidazoles, and carbazoles, undergo Ullmann couplings under mild conditions (room temperature) with an inexpensive catalyst (Cul, without an added ligand). by Junwon Choi. Ph. D. 2015-01-20T17:56:11Z 2015-01-20T17:56:11Z 2014 2014 Thesis http://hdl.handle.net/1721.1/93033 899241746 eng M.I.T. theses are protected by copyright. They may be viewed from this source for any purpose, but reproduction or distribution in any format is prohibited without written permission. See provided URL for inquiries about permission. http://dspace.mit.edu/handle/1721.1/7582 361 pages application/pdf Massachusetts Institute of Technology |
| spellingShingle | Chemistry. Choi, Junwon, Ph. D. Massachusetts Institute of Technology Nickel-catalyzed asymmetric cross-couplings of secondary alkyl electrophiles and photoinduced, copper-catalyzed C-N couplings |
| title | Nickel-catalyzed asymmetric cross-couplings of secondary alkyl electrophiles and photoinduced, copper-catalyzed C-N couplings |
| title_full | Nickel-catalyzed asymmetric cross-couplings of secondary alkyl electrophiles and photoinduced, copper-catalyzed C-N couplings |
| title_fullStr | Nickel-catalyzed asymmetric cross-couplings of secondary alkyl electrophiles and photoinduced, copper-catalyzed C-N couplings |
| title_full_unstemmed | Nickel-catalyzed asymmetric cross-couplings of secondary alkyl electrophiles and photoinduced, copper-catalyzed C-N couplings |
| title_short | Nickel-catalyzed asymmetric cross-couplings of secondary alkyl electrophiles and photoinduced, copper-catalyzed C-N couplings |
| title_sort | nickel catalyzed asymmetric cross couplings of secondary alkyl electrophiles and photoinduced copper catalyzed c n couplings |
| topic | Chemistry. |
| url | http://hdl.handle.net/1721.1/93033 |
| work_keys_str_mv | AT choijunwonphdmassachusettsinstituteoftechnology nickelcatalyzedasymmetriccrosscouplingsofsecondaryalkylelectrophilesandphotoinducedcoppercatalyzedcncouplings |