자료유형  

 학위논문

Control Number  

0017163510

International Standard Book Number  

9798384449539

Dewey Decimal Classification Number  

547

Main Entry-Personal Name  

Yu, Isaac Fu-Ray.

Publication, Distribution, etc. (Imprint  

[S.l.] : University of California, Berkeley., 2024

Publication, Distribution, etc. (Imprint  

Ann Arbor : ProQuest Dissertations & Theses, 2024

Physical Description  

588 p.

General Note  

Source: Dissertations Abstracts International, Volume: 86-04, Section: B.

General Note  

Advisor: Hartwig, John F.

Dissertation Note  

Thesis (Ph.D.)--University of California, Berkeley, 2024.

Summary, Etc.  

요약The following dissertation discusses the development of iridium catalysts for the undirected borylation of alkyl C-H bonds and includes in-depth studies on the mechanism of these transformations.Chapter 1 contains a comprehensive review of applications of the borylation of C-H bonds catalyzed by transition metals to the synthesis of complex molecules. This review is subdivided into sections highlighting the state-of-the-art of methodology of the undirected and directed borylation of aryl and alkyl C-H bonds, and focuses on the utility of these reactions for the syntheses of drug precursors, complex bioactive molecules, and optoelectronic materials. Additionally, the review contains a generalized overview of mechanisms by which these reactions occur. Finally, this review provides the author's opinion on future directions for research on the borylation of alkyl C-H bonds.Chapter 2 describes the development of iridium-catalyzed borylation of the bridgehead, tertiary C-H bonds of bicyclopentanes and bicyclohexanes. Contained is an examination of the scope of the borylation of bicyclopentanes, bicyclohexanes, oxabicyclohexanes, and azabicyclohexanes. Also included are experimental and computational studies that reveal the mechanism of this reaction.Chapter 3 discusses the development of catalysts that enable the borylation of alkyl C- H bonds to occur at mild temperatures (65 ºC). Key to this development was the discovery that catalysts formed from 2-aminophenanthrolines and iridium undergo rapid activation and catalyze the borylation of alkyl C-H bonds at reduced temperatures, maintaining activity even at room temperature. Also included are experimental studies that provide initial information on the identity of the active catalyst species.Chapter 4 describes the mechanistic study of the origin of improved activation and reaction rates of the borylation of alkyl C-H bonds catalyzed by 2-aminophenanthroline complexes. Experimental studies enabled by a sterically protected aminophenanthroline demonstrate that the N-boryl iridium trisboryl complex is the resting state and that the corresponding N-boryl iridium bis boryl hydride complex is inactive for the borylation reaction.

Subject Added Entry-Topical Term  

Organic chemistry.

Subject Added Entry-Topical Term  

Chemistry.

Subject Added Entry-Topical Term  

Analytical chemistry.

Index Term-Uncontrolled  

C-H bonds

Index Term-Uncontrolled  

Iridium catalysts

Index Term-Uncontrolled  

Borylation

Index Term-Uncontrolled  

Bicyclopentanes

Added Entry-Corporate Name  

University of California, Berkeley Chemistry

Host Item Entry  

Dissertations Abstracts International. 86-04B.

Electronic Location and Access  

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Control Number  

joongbu:655535