Computational study on the origins of asymmetric induction in Pd-catalyzed cross-coupling reactions and suggestions for improvements thereupon
Thesis (S.M.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2008.
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| Format: | Thesis |
| Language: | eng |
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Massachusetts Institute of Technology
2008
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| Online Access: | http://hdl.handle.net/1721.1/42916 |
| _version_ | 1826213076022591488 |
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| author | Huhn, Richard A. (Richard Andrew) |
| author2 | Stephen L. Buchwald. |
| author_facet | Stephen L. Buchwald. Huhn, Richard A. (Richard Andrew) |
| author_sort | Huhn, Richard A. (Richard Andrew) |
| collection | MIT |
| description | Thesis (S.M.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2008. |
| first_indexed | 2024-09-23T15:42:58Z |
| format | Thesis |
| id | mit-1721.1/42916 |
| institution | Massachusetts Institute of Technology |
| language | eng |
| last_indexed | 2024-09-23T15:42:58Z |
| publishDate | 2008 |
| publisher | Massachusetts Institute of Technology |
| record_format | dspace |
| spelling | mit-1721.1/429162019-04-12T09:47:57Z Computational study on the origins of asymmetric induction in Pd-catalyzed cross-coupling reactions and suggestions for improvements thereupon Huhn, Richard A. (Richard Andrew) Stephen L. Buchwald. Massachusetts Institute of Technology. Dept. of Chemistry. Massachusetts Institute of Technology. Dept. of Chemistry. Chemistry. Thesis (S.M.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2008. This electronic version was submitted by the student author. The certified thesis is available in the Institute Archives and Special Collections. Includes bibliographical references. The origins of asymmetric induction in the Suzuki-Miyaura cross coupling reaction are investigated computationally with density functional theory. Monophosphine-bound palladium complexes are analyzed in the context of oxidative addition to aryl halides, and ligands are explored in terms of steric and electronic effects relevant to oxidative addition. As one of the most successful ligands to date for the asymmetric Suzuki reaction, KenPhos is given substantial attention and subjected to detailed structural analysis. The analysis leads to proposals for new ligands that may enhance the asymmetry of oxidative addition, and some initial synthetic work in that capacity is presented Thesis Supervisor: Professor Stephen L. Buchwald by Richard A. Huhn. S.M. 2008-11-07T14:10:04Z 2008-11-07T14:10:04Z 2008 2008 Thesis http://hdl.handle.net/1721.1/42916 244442844 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 223 p. application/pdf Massachusetts Institute of Technology |
| spellingShingle | Chemistry. Huhn, Richard A. (Richard Andrew) Computational study on the origins of asymmetric induction in Pd-catalyzed cross-coupling reactions and suggestions for improvements thereupon |
| title | Computational study on the origins of asymmetric induction in Pd-catalyzed cross-coupling reactions and suggestions for improvements thereupon |
| title_full | Computational study on the origins of asymmetric induction in Pd-catalyzed cross-coupling reactions and suggestions for improvements thereupon |
| title_fullStr | Computational study on the origins of asymmetric induction in Pd-catalyzed cross-coupling reactions and suggestions for improvements thereupon |
| title_full_unstemmed | Computational study on the origins of asymmetric induction in Pd-catalyzed cross-coupling reactions and suggestions for improvements thereupon |
| title_short | Computational study on the origins of asymmetric induction in Pd-catalyzed cross-coupling reactions and suggestions for improvements thereupon |
| title_sort | computational study on the origins of asymmetric induction in pd catalyzed cross coupling reactions and suggestions for improvements thereupon |
| topic | Chemistry. |
| url | http://hdl.handle.net/1721.1/42916 |
| work_keys_str_mv | AT huhnrichardarichardandrew computationalstudyontheoriginsofasymmetricinductioninpdcatalyzedcrosscouplingreactionsandsuggestionsforimprovementsthereupon |