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Pd-Catalyzed Functionalization of Di...

Tanaka, Keita .

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Pd-Catalyzed Functionalization of Distal C-H Bonds.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Pd-Catalyzed Functionalization of Distal C-H Bonds./
Author:	Tanaka, Keita .
Published:	Ann Arbor : ProQuest Dissertations & Theses, : 2020,
Description:	385 p.
Notes:	Source: Dissertations Abstracts International, Volume: 82-01, Section: B.
Contained By:	Dissertations Abstracts International82-01B.
Subject:	Organic chemistry. -
Online resource:	https://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=27669332
ISBN:	9798662411791

Pd-Catalyzed Functionalization of Distal C-H Bonds.
Tanaka, Keita .

Pd-Catalyzed Functionalization of Distal C-H Bonds. - Ann Arbor : ProQuest Dissertations & Theses, 2020 - 385 p.

Source: Dissertations Abstracts International, Volume: 82-01, Section: B.

Thesis (Ph.D.)--The Scripps Research Institute, 2020.

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

Direct conversion of targeted C-H bonds into desired functional groups is the most ideal transformation in the organic synthesis, simplifying the preparation of complex molecules. Countless research efforts by a number of researchers improved the scope of substrates and transformations, however there is a lot of room for improvement in terms of the site-selectivity. One of the powerful strategies to achieve the desired selectivity is to use directing groups. The major problem of this strategy is that as the distance between the targeted C-H bond and the directing group gets large, both reactivity and selectivity drop significantly. Since Pd catalysis can enable a wide range of C-C and C-heteroatom bond formation reactions, the development of Pd-catalyzed remote C-H functionalization is the major focus of this thesis.The work in this dissertation is divided into two parts. Part I describes the development of a bifunctional template for the selective remote C-H functionalization of aromatic nitrogen heterocycles. We have achieved meta-C-H activation of arenes by developing a template where the directing group and substrate are connected by the linker. However, this method was not applicable to aromatic nitrogen heterocycles, which have no functional group handles to install the templates. Here, a bifunctional template was developed, which could be installed on the substrates by means of coordination, and it allowed to achieve selective functionalization of distal C-H bonds in various aromatic nitrogen heterocycles. Part II describes the development of a new auxiliary for the C(sp3)-H functionalization of alcohols. Pd-catalyzed C(sp3)-H activation of alcohols typically shows β-selectivity due to the required distance between the chelating atom in the attached directing group and the targeted C-H bonds. Herein we report the design of a hemilabile directing group which exploits the chelation of a readily removable benzyl ether moiety to direct γ- or δ-C-H carbonylation and olefination of alcohols.

ISBN: 9798662411791Subjects--Topical Terms:

523952
Organic chemistry.
Subjects--Index Terms:

Alcohols

Pd-Catalyzed Functionalization of Distal C-H Bonds.
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520 $a Direct conversion of targeted C-H bonds into desired functional groups is the most ideal transformation in the organic synthesis, simplifying the preparation of complex molecules. Countless research efforts by a number of researchers improved the scope of substrates and transformations, however there is a lot of room for improvement in terms of the site-selectivity. One of the powerful strategies to achieve the desired selectivity is to use directing groups. The major problem of this strategy is that as the distance between the targeted C-H bond and the directing group gets large, both reactivity and selectivity drop significantly. Since Pd catalysis can enable a wide range of C-C and C-heteroatom bond formation reactions, the development of Pd-catalyzed remote C-H functionalization is the major focus of this thesis.The work in this dissertation is divided into two parts. Part I describes the development of a bifunctional template for the selective remote C-H functionalization of aromatic nitrogen heterocycles. We have achieved meta-C-H activation of arenes by developing a template where the directing group and substrate are connected by the linker. However, this method was not applicable to aromatic nitrogen heterocycles, which have no functional group handles to install the templates. Here, a bifunctional template was developed, which could be installed on the substrates by means of coordination, and it allowed to achieve selective functionalization of distal C-H bonds in various aromatic nitrogen heterocycles. Part II describes the development of a new auxiliary for the C(sp3)-H functionalization of alcohols. Pd-catalyzed C(sp3)-H activation of alcohols typically shows β-selectivity due to the required distance between the chelating atom in the attached directing group and the targeted C-H bonds. Herein we report the design of a hemilabile directing group which exploits the chelation of a readily removable benzyl ether moiety to direct γ- or δ-C-H carbonylation and olefination of alcohols.
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