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Exploration of Novel C-H Functionalization Methodologies via Organic Photoredox Catalysis /

紀錄類型:	書目-電子資源 : Monograph/item
正題名/作者:	Exploration of Novel C-H Functionalization Methodologies via Organic Photoredox Catalysis /Alexander Joseph Boley.
作者:	Boley, Alexander Joseph,
面頁冊數:	1 electronic resource (133 pages)
附註:	Source: Dissertations Abstracts International, Volume: 87-02, Section: B.
附註:	Advisors: Niewicz, David A. Committee members: Meek, Simon J.; Wilkerson-Hill, Sidney M.; Aubé, Jeffrey; Templeton, Joseph L.
Contained By:	Dissertations Abstracts International87-02B.
標題:	Organic chemistry.
電子資源:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=32122390
ISBN:	9798291561287

Exploration of Novel C-H Functionalization Methodologies via Organic Photoredox Catalysis /
Boley, Alexander Joseph,

Exploration of Novel C-H Functionalization Methodologies via Organic Photoredox Catalysis /Alexander Joseph Boley. - 1 electronic resource (133 pages)

Source: Dissertations Abstracts International, Volume: 87-02, Section: B.

The selective and facile functionalization of C-H bonds - the most abundant bonds in all chemical space - remains a key driving factor for innovation in modern chemistry. Chapter 1 provides an overview of C-H functionalization research and its importance; discussion of C-H functionalization necessitates an analysis of subjects such as organometallic chemistry, radical generation and functionalization, and the synthetic benefits and challenges presented therein. Intersecting with discussion of C-H functionalization and radical chemistry, photoredox catalysis has played a major role in modern C-H functionalization methodologies, and as such is discussed in detail. Distinct and impactful C-H functionalization works from the Nicewicz lab are explored, providing a basis for the exploratory photoredox catalysis chemistry discussed in subsequent chapters.Chapter 2 explores attempts at generating and functionalizing azaallyl radical species via organic photoredox catalysis. Using the extreme oxidizing power of acridinium photoredox catalysts for novel modes of C-H functionalization circumvents the typically harsh conditions needed for azaallyl radical formation. While methods for α-amino functionalization are abundant, azaallyl radicals are uniquely long-lived, allowing for radical cascade and cyclization reactivity. While some success was afforded C-H functionalization with typical radical traps, control of the reactivity remains tenuous and the desired cascade-like cyclization remains elusive. Chapter 3 details a completed C-H functionalization methodology for the programmable synthesis of decorated piperazine cores via organic photoredox catalysis. The synthetic and medicinal importance piperazines is highlighted, as are the typical shortcomings of both traditional and state-of-the-art approaches for their synthesis. Optimization and scope of the cyclization reaction are explored in depth, and a complementary hydroamination strategy for the synthesis of complex diamine backbones from ene-carbamates via organic photoredox catalysis is demonstrated. Chapter 4 serves as a conceptual successor to the piperazine methodology, establishing the foundation of a synthetic approach for an organic photoredox-catalyzed morpholine synthesis via a C-H functionalization strategy. Initial optimization of the desired reactivity is detailed in full, exploring somewhat divergent results based on seemingly innocuous changes to the reaction system. While the yield in either iteration of the model system remains low, significant options for future optimization remain in terms of catalyst choice and substrate design.

English

ISBN: 9798291561287Subjects--Topical Terms:

708640
Organic chemistry.
Subjects--Index Terms:

C-H functionalization

Exploration of Novel C-H Functionalization Methodologies via Organic Photoredox Catalysis /
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520 $a The selective and facile functionalization of C-H bonds - the most abundant bonds in all chemical space - remains a key driving factor for innovation in modern chemistry. Chapter 1 provides an overview of C-H functionalization research and its importance; discussion of C-H functionalization necessitates an analysis of subjects such as organometallic chemistry, radical generation and functionalization, and the synthetic benefits and challenges presented therein. Intersecting with discussion of C-H functionalization and radical chemistry, photoredox catalysis has played a major role in modern C-H functionalization methodologies, and as such is discussed in detail. Distinct and impactful C-H functionalization works from the Nicewicz lab are explored, providing a basis for the exploratory photoredox catalysis chemistry discussed in subsequent chapters.Chapter 2 explores attempts at generating and functionalizing azaallyl radical species via organic photoredox catalysis. Using the extreme oxidizing power of acridinium photoredox catalysts for novel modes of C-H functionalization circumvents the typically harsh conditions needed for azaallyl radical formation. While methods for α-amino functionalization are abundant, azaallyl radicals are uniquely long-lived, allowing for radical cascade and cyclization reactivity. While some success was afforded C-H functionalization with typical radical traps, control of the reactivity remains tenuous and the desired cascade-like cyclization remains elusive. Chapter 3 details a completed C-H functionalization methodology for the programmable synthesis of decorated piperazine cores via organic photoredox catalysis. The synthetic and medicinal importance piperazines is highlighted, as are the typical shortcomings of both traditional and state-of-the-art approaches for their synthesis. Optimization and scope of the cyclization reaction are explored in depth, and a complementary hydroamination strategy for the synthesis of complex diamine backbones from ene-carbamates via organic photoredox catalysis is demonstrated. Chapter 4 serves as a conceptual successor to the piperazine methodology, establishing the foundation of a synthetic approach for an organic photoredox-catalyzed morpholine synthesis via a C-H functionalization strategy. Initial optimization of the desired reactivity is detailed in full, exploring somewhat divergent results based on seemingly innocuous changes to the reaction system. While the yield in either iteration of the model system remains low, significant options for future optimization remain in terms of catalyst choice and substrate design.
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650 4 $a Physical chemistry. $3 708580
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653 $a C-H functionalization
653 $a Catalysis
653 $a Photoredox catalysis
653 $a Hydroamination
653 $a Piperazine methodology
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710 2 $a The University of North Carolina at Chapel Hill. $b Chemistry. $3 660291
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