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Making and Breaking C--F Bonds via P...

Thornbury, Richard Tresslar.

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Making and Breaking C--F Bonds via Palladium-Catalysis.

紀錄類型:	書目-電子資源 : Monograph/item
正題名/作者:	Making and Breaking C--F Bonds via Palladium-Catalysis./
作者:	Thornbury, Richard Tresslar.
出版者:	Ann Arbor : ProQuest Dissertations & Theses, : 2018,
面頁冊數:	215 p.
附註:	Source: Dissertation Abstracts International, Volume: 80-03(E), Section: B.
Contained By:	Dissertation Abstracts International80-03B(E).
標題:	Organic chemistry. -
電子資源:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=10813662
ISBN:	9780438653979

Making and Breaking C--F Bonds via Palladium-Catalysis.
Thornbury, Richard Tresslar.

Making and Breaking C--F Bonds via Palladium-Catalysis. - Ann Arbor : ProQuest Dissertations & Theses, 2018 - 215 p.

Source: Dissertation Abstracts International, Volume: 80-03(E), Section: B.

Thesis (Ph.D.)--University of California, Berkeley, 2018.

Chapter 1: A ligand controlled, palladium-catalyzed, enantioselective 1,3-arylfluorination of [2H]-chromenes was developed. The products were obtained in high enantioselectivity and with a syn- relationship of the introduced substituents. The pyranyl fluoride products were further derivatized to demonstrate the utility of the products. A ligand dependent divergent formation of 1,3- and 2,1- alkene difunctionalization products was also observed. This bifurcation in reactivity was investigated with a combination of experimental, computational, and statistical analysis tools. Ultimately, the site selectivity was found to be dependent on the ligand denticity and metal electrophilicity, the electronics of the boronic acid, and the donor ability of the directing group in the substrate.

ISBN: 9780438653979Subjects--Topical Terms:

523952
Organic chemistry.

Making and Breaking C--F Bonds via Palladium-Catalysis.
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520 $a Chapter 1: A ligand controlled, palladium-catalyzed, enantioselective 1,3-arylfluorination of [2H]-chromenes was developed. The products were obtained in high enantioselectivity and with a syn- relationship of the introduced substituents. The pyranyl fluoride products were further derivatized to demonstrate the utility of the products. A ligand dependent divergent formation of 1,3- and 2,1- alkene difunctionalization products was also observed. This bifurcation in reactivity was investigated with a combination of experimental, computational, and statistical analysis tools. Ultimately, the site selectivity was found to be dependent on the ligand denticity and metal electrophilicity, the electronics of the boronic acid, and the donor ability of the directing group in the substrate.
520 $a Chapter 2: A palladium-catalyzed defluorinative coupling of 1-aryl-2,2-difluoroalkenes with boronic acids was developed. Broad functional tolerance arises from a redox-neutral process in which a palladium(II) active species which is proposed to undergo a beta-fluoride elimination to afford the products. The monofluorostilbene products were formed with excellent diastereoselectivity (≥ 50:1) in all cases. As a demonstration of this method's unique combination of reactivity and functional group tolerance, a GleevecRTM analogue, using a monofluorostilbene as an amide isostere, was synthesized in 4 steps from commercially available materials.
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