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The Development of New Strategies to...

Evoniuk, Christopher J.

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The Development of New Strategies to Harness Radicals for the Preparation of N-heterocycles.

紀錄類型:	書目-電子資源 : Monograph/item
正題名/作者:	The Development of New Strategies to Harness Radicals for the Preparation of N-heterocycles./
作者:	Evoniuk, Christopher J.
出版者:	Ann Arbor : ProQuest Dissertations & Theses, : 2018,
面頁冊數:	288 p.
附註:	Source: Dissertation Abstracts International, Volume: 80-01(E), Section: B.
Contained By:	Dissertation Abstracts International80-01B(E).
標題:	Organic chemistry. -
電子資源:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=10750204
ISBN:	9780438306271

The Development of New Strategies to Harness Radicals for the Preparation of N-heterocycles.
Evoniuk, Christopher J.

The Development of New Strategies to Harness Radicals for the Preparation of N-heterocycles. - Ann Arbor : ProQuest Dissertations & Theses, 2018 - 288 p.

Source: Dissertation Abstracts International, Volume: 80-01(E), Section: B.

Thesis (Ph.D.)--The Florida State University, 2018.

This work focuses on the development of new synthetic methods for the preparation of various N-heterocycles. While I have encountered many road blocks throughout my PhD, it has taught me how to solve a wide variety of challenges through perseverance, critical thinking and collaboration. I have successfully developed multiple projects stemming from my independent ideas for new chemical transformations.

ISBN: 9780438306271Subjects--Topical Terms:

523952
Organic chemistry.

The Development of New Strategies to Harness Radicals for the Preparation of N-heterocycles.
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500 $a Source: Dissertation Abstracts International, Volume: 80-01(E), Section: B.
500 $a Adviser: Igor V. Alabugin.
502 $a Thesis (Ph.D.)--The Florida State University, 2018.
520 $a This work focuses on the development of new synthetic methods for the preparation of various N-heterocycles. While I have encountered many road blocks throughout my PhD, it has taught me how to solve a wide variety of challenges through perseverance, critical thinking and collaboration. I have successfully developed multiple projects stemming from my independent ideas for new chemical transformations.
520 $a The projects range from cyclizations of o-alkenylisocyanides using a variety of radical precursors to C(sp3)-H amination (with and without transition metals) reactions. The discovery of selective addition of radicals to isonitriles could be harnessed to initiate a radical cascade that was designed to overcome the stereoelectronic restrictions on homoallylic ring expansion in alkyne reactions by using alkenes as synthetic equivalents of alkynes. This allowed us to establish a new route for N-heteroaromatics by coupling a homoallylic ring expansion with a stereoelectronically assisted C-C bond scission to yield the formal "6-endo" products.
520 $a Additionally we have developed multiple protocols for C(sp3)-H aminations. Firstly, a transition metal mediated approach using FeCl 3/DDQ for an intramolecular C(sp3)-H oxidative amination. In this reaction, an aniline group can activate the molecule for single-electron-transfer while also acting as an internal nucleophile to trap reactive intermediates. Following a consecutive electron transfer oxidation process, we can couple free amines with -CH2- groups to afford aromatic N-heterocycles using inexpensive reagents.
520 $a Expansion of the intramolecular oxidative C(sp3)-H amination to unprotected anilines and amides and C(sp3)-H bonds to occur under mild conditions using t-BuOK, DMF and O2. This protocol relies on a synergy between base, radical and oxidizing species to promote a coordinated sequence of deprotonation followed by H-atom transfer and oxidation that constructs a new C-N bond. We were able to apply this chemistry to the preparation of a wide variety of N-heterocycles, ranging from small molecules to extended aromatics without the need for transition metals or strong oxidants.
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