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Nickel-Catalyzed Cross-Coupling Reac...

Hoerrner, Megan E.

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Nickel-Catalyzed Cross-Coupling Reactions Through C-O and C-N Bond Activation.

紀錄類型:	書目-電子資源 : Monograph/item
正題名/作者:	Nickel-Catalyzed Cross-Coupling Reactions Through C-O and C-N Bond Activation./
作者:	Hoerrner, Megan E.
出版者:	Ann Arbor : ProQuest Dissertations & Theses, : 2020,
面頁冊數:	693 p.
附註:	Source: Dissertations Abstracts International, Volume: 82-04, Section: B.
Contained By:	Dissertations Abstracts International82-04B.
標題:	Organic chemistry. -
電子資源:	https://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=27959206
ISBN:	9798672125985

Nickel-Catalyzed Cross-Coupling Reactions Through C-O and C-N Bond Activation.
Hoerrner, Megan E.

Nickel-Catalyzed Cross-Coupling Reactions Through C-O and C-N Bond Activation. - Ann Arbor : ProQuest Dissertations & Theses, 2020 - 693 p.

Source: Dissertations Abstracts International, Volume: 82-04, Section: B.

Thesis (Ph.D.)--University of Delaware, 2020.

This item must not be sold to any third party vendors.

This dissertation focuses on nickel-catalyzed cross-couplings of amine and alcohols via C-N and C-O bond activation. Chapter 1 focuses on the development of a stereospecific, nickel-catalyzed Suzuki-Miyaura cross-coupling of allylic pivalates to deliver quaternary stereocenters. The enantioenriched allylic pivalates are prepared easily in high yield and high ee. The reaction uses an inexpensive nickel catalyst and air-stable reagents. Both the aryl boroxine and allylic pivalate include broad functional group tolerance including heteroatoms.Chapter 2 focuses on the development of a nickel-catalyzed Suzuki-Miyaura arylation of amino acid-derived pyridinium salts. This reaction uses a privileged class of widely available and inexpensive substrates, amino acid derivatives, to deliver -aryl esters. The products can be easily hydrolyzed to carboxylates to make propionic acid derivatives. Notably, this reaction tolerates a broad range of functional groups due to the mild conditions used. Finally, a one-pot procedure was developed that may be advantageous for parallel synthesisChapter 3 focuses on the development of a deaminative reductive cross-electrophile coupling of alkylpyridinium salts and aryl bromides. Using mild, neutral conditions, we were able to overcome limitations of our previous chemistry and provide a method with broad functional group tolerance, including 2 and 3 pyridyl groups, heteroaryls, and protic groups. This method uses primary, secondary, and one tertiary alkyl pyridinium salts to make a wide variety of exceptional products.Chapter 4 focuses on the development of a nickel-catalyzed synthesis of ketones from the reductive coupling of N-alkyl pyridinium salts with activated carboxylic acids. This reaction takes advantage of inexpensive abundant starting materials amines and carboxylic acids and makes a desirable ketone product. The catalyst systems used are commercially available and a broad, diverse group of products are made, including those from pharmaceutical intermediates.

ISBN: 9798672125985Subjects--Topical Terms:

523952
Organic chemistry.
Subjects--Index Terms:

Nickel-catalyzed cross-couplings

Nickel-Catalyzed Cross-Coupling Reactions Through C-O and C-N Bond Activation.
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520 $a This dissertation focuses on nickel-catalyzed cross-couplings of amine and alcohols via C-N and C-O bond activation. Chapter 1 focuses on the development of a stereospecific, nickel-catalyzed Suzuki-Miyaura cross-coupling of allylic pivalates to deliver quaternary stereocenters. The enantioenriched allylic pivalates are prepared easily in high yield and high ee. The reaction uses an inexpensive nickel catalyst and air-stable reagents. Both the aryl boroxine and allylic pivalate include broad functional group tolerance including heteroatoms.Chapter 2 focuses on the development of a nickel-catalyzed Suzuki-Miyaura arylation of amino acid-derived pyridinium salts. This reaction uses a privileged class of widely available and inexpensive substrates, amino acid derivatives, to deliver -aryl esters. The products can be easily hydrolyzed to carboxylates to make propionic acid derivatives. Notably, this reaction tolerates a broad range of functional groups due to the mild conditions used. Finally, a one-pot procedure was developed that may be advantageous for parallel synthesisChapter 3 focuses on the development of a deaminative reductive cross-electrophile coupling of alkylpyridinium salts and aryl bromides. Using mild, neutral conditions, we were able to overcome limitations of our previous chemistry and provide a method with broad functional group tolerance, including 2 and 3 pyridyl groups, heteroaryls, and protic groups. This method uses primary, secondary, and one tertiary alkyl pyridinium salts to make a wide variety of exceptional products.Chapter 4 focuses on the development of a nickel-catalyzed synthesis of ketones from the reductive coupling of N-alkyl pyridinium salts with activated carboxylic acids. This reaction takes advantage of inexpensive abundant starting materials amines and carboxylic acids and makes a desirable ketone product. The catalyst systems used are commercially available and a broad, diverse group of products are made, including those from pharmaceutical intermediates.
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