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Palladacycles with palladium-bonded ...
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University of Kansas., Chemistry.
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Palladacycles with palladium-bonded stereogenic carbons: Tools for exploring reaction pathways in organometallic chemistry.
紀錄類型:
書目-電子資源 : Monograph/item
正題名/作者:
Palladacycles with palladium-bonded stereogenic carbons: Tools for exploring reaction pathways in organometallic chemistry./
作者:
Hershberger, John Charles.
面頁冊數:
428 p.
附註:
Adviser: Helena C. Malinakova.
Contained By:
Dissertation Abstracts International70-04B.
標題:
Chemistry, Inorganic. -
電子資源:
http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3354839
ISBN:
9781109124231
Palladacycles with palladium-bonded stereogenic carbons: Tools for exploring reaction pathways in organometallic chemistry.
Hershberger, John Charles.
Palladacycles with palladium-bonded stereogenic carbons: Tools for exploring reaction pathways in organometallic chemistry.
- 428 p.
Adviser: Helena C. Malinakova.
Thesis (Ph.D.)--University of Kansas, 2009.
Organometallic chemistry has undoubtedly changed the way synthetic chemists construct molecules as well as the way synthetic chemists think about constructing molecules. Three well-known and most widely used transition metal-catalyzed reactions are the cross-coupling reactions, the Heck reaction, and olefin metathesis. Reactions stoichiometric in the transition-metal played an important role in their development, providing insight that could have remained uncovered otherwise.
ISBN: 9781109124231Subjects--Topical Terms:
517253
Chemistry, Inorganic.
Palladacycles with palladium-bonded stereogenic carbons: Tools for exploring reaction pathways in organometallic chemistry.
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Organometallic chemistry has undoubtedly changed the way synthetic chemists construct molecules as well as the way synthetic chemists think about constructing molecules. Three well-known and most widely used transition metal-catalyzed reactions are the cross-coupling reactions, the Heck reaction, and olefin metathesis. Reactions stoichiometric in the transition-metal played an important role in their development, providing insight that could have remained uncovered otherwise.
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The first goal of this dissertation is to expand our understanding of how changing the ligand sphere around the palladium center (by utilizing a triphenylphosphine moiety attached to an insoluble polymer support) affects the reactivity of the palladacycles on solid-phase. More specifically, we compared the reactivity of polymer-bound palladacycles to their soluble triphenylphosphine analogs. The second goal of this dissertation is to elucidate how a carbon stereocenter bound to palladium transfers its asymmetry to a second newly formed stereocenter that is also bound to palladium, and the role played by the auxiliary ligand in this process.
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The first project detailed in this dissertation describes a basic study of the interactions between a solid-phase support and well-defined palladacycles. The effects of phosphorus loading, palladium loading, P : Pd ratio, and polymer swelling on the reactivity of the polymer-bound palladacycles were explored. The results of these studies as well as the facile syntheses of 2H-1 -benzopyrans are presented. We also attempted the synthesis of a library of highly substituted 1,2-dihydroquinolines utilizing this solid-phase technology. Although we were unable to successfully complete the library synthesis, future studies in this area are expected to further elucidate the difference in the reactivities of solid-phase oxa-palladacycles and solid-phase aza-palladacycles.
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The second project describes the successful development of an expeditious route to palladapyrrolidinones, a new organometallic scaffold featuring two Csp3-hybridized stereogenic carbons attached to a palladium center. These are rare examples of palladium complexes bearing two stereogenic carbons bound to a palladium center. It is also the first system in which the effect of an existing carbon stereocenter bound directly to a palladium center upon the formation of a second stereocenter also directly bound to palladium can be studied in detail. Up to 20 : 1 diastereoselectivity was observed during the formation of the second stereocenter and the diastereoselectivity is shown to be ligand-dependent, indicating that the auxiliary ligand sphere plays a significant role in diastereoinduction. Rather unexpectedly, utilizing a chiral non-racemic ligand in the synthesis of palladapyrrolidinones had little effect on the diastereoselectivity of the reaction. A model to explain the diastereoselectivity and the surprising lack of influence of the chiral non-racemic ligand on the diastereoselectivity is proposed based on X-ray structural studies.
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http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3354839
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