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Ligand-Enabled Pd-catalyzed C(sp3)-H Functionalization of Carboxylic Acids and Amines.

紀錄類型:	書目-電子資源 : Monograph/item
正題名/作者:	Ligand-Enabled Pd-catalyzed C(sp3)-H Functionalization of Carboxylic Acids and Amines./
作者:	Qian, Shaoqun.
面頁冊數:	1 online resource (380 pages)
附註:	Source: Dissertations Abstracts International, Volume: 84-07, Section: B.
Contained By:	Dissertations Abstracts International84-07B.
標題:	Organic chemistry. -
電子資源:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=29397873click for full text (PQDT)
ISBN:	9798368412191

Ligand-Enabled Pd-catalyzed C(sp3)-H Functionalization of Carboxylic Acids and Amines.
Qian, Shaoqun.

Ligand-Enabled Pd-catalyzed C(sp3)-H Functionalization of Carboxylic Acids and Amines. - 1 online resource (380 pages)

Source: Dissertations Abstracts International, Volume: 84-07, Section: B.

Thesis (Ph.D.)--The Scripps Research Institute, 2023.

Includes bibliographical references

Palladium-catalyzed C(sp3)-H functionalizations directed by native functional group such as amines and carboxylic acids have recently become the focus of scientific interest as it eliminates the needs for laborious directing group manipulations and significantly elevate the atom efficiency of C-H functionalization reactions. Herein, we have developed three new methods for the palladium-catalyzed C(sp3)-H functionalizations of carboxylic acids and amines. Firstly, a new Pd(II)-catalyzed C(sp3)-H lactonization of o-methyl benzoic acid substrates using molecular oxygen as oxidant has been realized by employing 2-pyridone as ligand (Chapter 2). This finding provides a rare example of C-H oxygenation through Pd(II)/Pd(0) catalysis, as well as a method to construct biologically important benzolactone scaffolds. The use of a gas mixture of 5% oxygen in nitrogen demonstrated the possibility for its application in pharmaceutical manufacturing. Next, as part of our research program aimed at developing new C-H functionalization reactions that rapidly increase molecular complexity, we developed a novel Pd(II)-catalyzed tandem intramolecular β-C(sp3)-H olefination and lactonization reaction that rapidly transforms linear carboxylic acid possessing a tethered olefin into the biologically important bicyclo[3.2.1] lactone motif (Chapter 3). Additionally, we demonstrate the synthetic potential of this annulation by constructing the 6,6,5-tricyclic lactone core structure of the meroterpenoid cochlactone A. Finally, we have developed a novel Pd(II)-catalyzed synthesis of bicyclo[3.2.1] pyrrolidines via tandem intramolecular γ-C(sp3)-H olefination and cyclization of alkyl amines (Chapter 4). We anticipate that those compelling reactions may provide a novel synthetic disconnection that can be broadly applied towards the preparation of a variety of bioactive natural products.

Electronic reproduction.
Ann Arbor, Mich. :
ProQuest,
2023

Mode of access: World Wide Web

ISBN: 9798368412191Subjects--Topical Terms:

523952
Organic chemistry.
Subjects--Index Terms:

C-H functionalizationIndex Terms--Genre/Form:

542853
Electronic books.

Ligand-Enabled Pd-catalyzed C(sp3)-H Functionalization of Carboxylic Acids and Amines.
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