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Nickel Catalysis: Asymmetric Arylati...

Shields, Jason Daniel.

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Nickel Catalysis: Asymmetric Arylation of Quinolinium Ions and the Development of an Air-Stable Precatalyst.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Nickel Catalysis: Asymmetric Arylation of Quinolinium Ions and the Development of an Air-Stable Precatalyst./
Author:	Shields, Jason Daniel.
Published:	Ann Arbor : ProQuest Dissertations & Theses, : 2015,
Description:	143 p.
Notes:	Source: Dissertation Abstracts International, Volume: 77-03(E), Section: B.
Contained By:	Dissertation Abstracts International77-03B(E).
Subject:	Organic chemistry. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3729709
ISBN:	9781339156637

Nickel Catalysis: Asymmetric Arylation of Quinolinium Ions and the Development of an Air-Stable Precatalyst.
Shields, Jason Daniel.

Nickel Catalysis: Asymmetric Arylation of Quinolinium Ions and the Development of an Air-Stable Precatalyst. - Ann Arbor : ProQuest Dissertations & Theses, 2015 - 143 p.

Source: Dissertation Abstracts International, Volume: 77-03(E), Section: B.

Thesis (Ph.D.)--Princeton University, 2015.

Although both palladium and nickel were reported to catalyze cross-coupling reactions some four decades ago, palladium became the catalyst of choice for most chemists, due in part to the greater air stability of Pd(0) relative to Ni(0). Nevertheless, nickel is a desirable catalyst for two reasons. First, nickel is three orders of magnitude less expensive than palladium. Second, nickel offers reactivity distinct from palladium due in part to the difference in electronegativity between the metals---for example, palladium is more likely to mediate C--H activation, while nickel more readily reacts with pi-systems, effecting cyclization reactions of olefins.

ISBN: 9781339156637Subjects--Topical Terms:

523952
Organic chemistry.

Nickel Catalysis: Asymmetric Arylation of Quinolinium Ions and the Development of an Air-Stable Precatalyst.
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245 1 0 $a Nickel Catalysis: Asymmetric Arylation of Quinolinium Ions and the Development of an Air-Stable Precatalyst.
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300 $a 143 p.
500 $a Source: Dissertation Abstracts International, Volume: 77-03(E), Section: B.
500 $a Adviser: Abigail G. Doyle.
502 $a Thesis (Ph.D.)--Princeton University, 2015.
520 $a Although both palladium and nickel were reported to catalyze cross-coupling reactions some four decades ago, palladium became the catalyst of choice for most chemists, due in part to the greater air stability of Pd(0) relative to Ni(0). Nevertheless, nickel is a desirable catalyst for two reasons. First, nickel is three orders of magnitude less expensive than palladium. Second, nickel offers reactivity distinct from palladium due in part to the difference in electronegativity between the metals---for example, palladium is more likely to mediate C--H activation, while nickel more readily reacts with pi-systems, effecting cyclization reactions of olefins.
520 $a In this dissertation, we describe two projects that leverage these advantages. First, we discuss the application of a nickel-iminium activation mode to an enantioselective crosscoupling reaction between arylboroxines and quinolinium ions. This reaction allows access to enantioenriched 2-aryl-1,2-dihydroquinolines with unprecedented stereoselectivity. A necessary step in the optimization of this reaction was the use of an unusual precatalyst, [(methallyl)NiCl] 2, instead of the more commonly used Ni(cod)2.
520 $a Second, we detail the development of [(TMEDA)Ni(o-tolyl)Cl], a modular, airstable nickel precatalyst. We believe this nickel source is a useful alternative to other nickel precatalysts reported in the literature. Due to the lability of TMEDA, this complex can be used in conjunction with mono- and bidentate phosphines, diimines, and NHC ligands, which is crucial to its success as a precatalyst in Suzuki--Miyaura, Buchwald--Hartwig, cyclization, and oxidative coupling reactions.
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