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Catalytic Radical Synthesis via Metal Hydrogen-Atom Transfer

Sise, Henry
http://rave.ohiolink.edu/etdc/view?acc_num=osu1714746998641642

Abstract Details

2024, Doctor of Philosophy, Ohio State University, Chemistry.
There is a constant need for the development of streamlined and efficient methods to rapidly introduce molecular complexity. Methods that rely on traditional functional group interconversion often become lengthy and suffer detrimental side reactivity when other reactive moieties are present. To address this challenge, C-H functionalization has emerged as a powerful tool to rapidly synthesize and diversify molecules. C-H bonds are ubiquitous within organic molecules. C-H functionalization allows the direct conversion of C-H bonds to a more valuable functional group. However, because of the small distinctions between C-H bonds, selective C-H functionalization presents unique challenges to overcome. Using bespoke radical chaperones paired with Metal Hydrogen-Atom Transfer, three selective transformations of simple alcohols and amines to more medicinally relevant motifs have been developed. (1) By pairing MHAT with photocatalysis we have developed a dual Co/Ir-catalyzed aza-Heck cyclization to synthesize vinyl oxazolines and oxazoles from allylic alcohol-derived oxime imidates, overcoming previous Pd-based limitations. (2) Towards the construction of various heterocycles, we have developed a strategy to convert amines to a variety of sultams utilizing metal hydrogen atom transfer (MHAT). (3) Utilizing chiral copper catalysis, enantioselective -amination of amines to synthesize chiral diamines has also been achieved via regioselective 1,5-hydrogen atom transfer.
David Nagib (Advisor)
Jon Parquette (Committee Member)
Christo Sevov (Committee Member)
323 p.
Chemistry
Metal Hydrogen Atom Transfer, Catalysis, Photochemistry, method development, radicals

Recommended Citations

Citations

  • Sise, H. (2024). Catalytic Radical Synthesis via Metal Hydrogen-Atom Transfer [Doctoral dissertation, Ohio State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=osu1714746998641642

    APA Style (7th edition)

  • Sise, Henry. Catalytic Radical Synthesis via Metal Hydrogen-Atom Transfer. 2024. Ohio State University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=osu1714746998641642.

    MLA Style (8th edition)

  • Sise, Henry. "Catalytic Radical Synthesis via Metal Hydrogen-Atom Transfer." Doctoral dissertation, Ohio State University, 2024. http://rave.ohiolink.edu/etdc/view?acc_num=osu1714746998641642

    Chicago Manual of Style (17th edition)

osu1714746998641642
© 2024, all rights reserved.
This open access ETD is published by The Ohio State University and OhioLINK.
Release 3.2.12