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Part I: Probing the limits of C-H fu...

Bedell, Thomas Aaron.

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Part I: Probing the limits of C-H functionalization methods with secondary metabolites: Synthesis of a benzo-fused indoxamycin core. Part II: Uranyl cation as a photocatalyst for Csp3-H fluorination.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Part I: Probing the limits of C-H functionalization methods with secondary metabolites: Synthesis of a benzo-fused indoxamycin core. Part II: Uranyl cation as a photocatalyst for Csp3-H fluorination./
Author:	Bedell, Thomas Aaron.
Description:	197 p.
Notes:	Source: Dissertation Abstracts International, Volume: 77-11(E), Section: B.
Contained By:	Dissertation Abstracts International77-11B(E).
Subject:	Organic chemistry. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=10120416
ISBN:	9781339815985

Part I: Probing the limits of C-H functionalization methods with secondary metabolites: Synthesis of a benzo-fused indoxamycin core. Part II: Uranyl cation as a photocatalyst for Csp3-H fluorination.
Bedell, Thomas Aaron.

Part I: Probing the limits of C-H functionalization methods with secondary metabolites: Synthesis of a benzo-fused indoxamycin core. Part II: Uranyl cation as a photocatalyst for Csp3-H fluorination. - 197 p.

Source: Dissertation Abstracts International, Volume: 77-11(E), Section: B.

Thesis (Ph.D.)--Princeton University, 2016.

Methods for functionalizing carbon-hydrogen bonds are featured in a new synthesis of the tricyclic core architecture that characterizes the indoxamycin family of secondary metabolites. A unique collaboration between four laboratories has engendered a design for synthesis featuring two sequential C--H functionalization reactions: a diastereoselective dirhodium-carbene insertion followed by an ester-directed, oxidative Heck cyclization to rapidly assemble the congested tricyclic core of the indoxamycins. This project exemplifies how multi-laboratory collaborations can foster conceptually novel approaches to challenging problems in chemical synthesis.

ISBN: 9781339815985Subjects--Topical Terms:

523952
Organic chemistry.

Part I: Probing the limits of C-H functionalization methods with secondary metabolites: Synthesis of a benzo-fused indoxamycin core. Part II: Uranyl cation as a photocatalyst for Csp3-H fluorination.
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020 $a 9781339815985
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100 1 $a Bedell, Thomas Aaron. $3 3192788
245 1 0 $a Part I: Probing the limits of C-H functionalization methods with secondary metabolites: Synthesis of a benzo-fused indoxamycin core. Part II: Uranyl cation as a photocatalyst for Csp3-H fluorination.
300 $a 197 p.
500 $a Source: Dissertation Abstracts International, Volume: 77-11(E), Section: B.
500 $a Adviser: Erik J. Sorensen.
502 $a Thesis (Ph.D.)--Princeton University, 2016.
520 $a Methods for functionalizing carbon-hydrogen bonds are featured in a new synthesis of the tricyclic core architecture that characterizes the indoxamycin family of secondary metabolites. A unique collaboration between four laboratories has engendered a design for synthesis featuring two sequential C--H functionalization reactions: a diastereoselective dirhodium-carbene insertion followed by an ester-directed, oxidative Heck cyclization to rapidly assemble the congested tricyclic core of the indoxamycins. This project exemplifies how multi-laboratory collaborations can foster conceptually novel approaches to challenging problems in chemical synthesis.
520 $a The fluorination of unactivated Csp3--H bonds remains a highly desirable and challenging transformation for pharmaceutical, agricultural, imaging, and materials scientists. Previous methods to accomplish this transformation have used bench-stable fluorine atom sources; however, many still rely on the use of UV-active photocatalysts for the requisite high-energy hydrogen atom abstraction event. Uranyl nitrate hexahydrate as a convenient, hydrogen atom abstraction catalyst that can fluorinate certain alkanes, in some cases with high efficiency and selectivity. This earth-abundant photocatalyst functions under visible light irradiation and exhibits remarkable selectivity in comparison to the previously-reported, UV-active species.
590 $a School code: 0181.
650 4 $a Organic chemistry. $3 523952
690 $a 0490
710 2 $a Princeton University. $b Chemistry. $3 2094742
773 0 $t Dissertation Abstracts International $g 77-11B(E).
790 $a 0181
791 $a Ph.D.
792 $a 2016
793 $a English
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=10120416