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Palladium-Catalyzed Carbocyclizations of Substituted Benzoic Acids and Tandem One-Pot Acyl Heck/Heck Coupling of Indanones

Miles, Kelsey C
http://rave.ohiolink.edu/etdc/view?acc_num=osu1377003454

Abstract Details

2013, Master of Science, Ohio State University, Chemistry.
Indanones and indenones are common structural motifs found in pharmaceuticals and biologically active natural products. Transition metal-catalyzed annulation processes represent the most current methods of synthesizing these attractive targets. However, the known methods to synthesize indanones and indenones generally suffer from poor regioselectivity, excess waste production, the use of high pressures of carbon monoxide, and/or poor functional group tolerance. The preparation of exo-methylene indanones and indenones from a novel palladium-catalyzed acyl-Heck cyclization of substituted benzoic acids is described herein. Formation of either the exo-methylene indanones or indenones can be controlled by simply changing the ligand. Low palladium loadings of 1 mol % provides moderate to excellent yields with broad functional group tolerance. Moreover, acetic acid is the only stoichiometric byproduct produced in this process. The degradation of the Pd(OAc)2/P(o-tol)3 used to form exo-methylene indanones into the well-known Herrmann-Beller palladacycle was observed and utilized in a tandem one-pot coupling process. This palladacycle is a robust Heck coupling catalyst, and because it is in the presence of a newly formed alkene, simply adding an arylbromide and a base provided access to a variety of aryl substituted exo-methylene indanones. Markedly, the synthesis of Indanorine, an antiproliferative agent, was achieved in good yield. Further application of this method toward the synthesis of donepezil which is marketed by Pfizer as Aricept (donepezil HCl) for the treatment of mild, moderate , and severe Alzheimer’s disease is also reported.
James Stambuli (Advisor)
Jon Parquette (Committee Member)
181 p.
Chemistry

Recommended Citations

Citations

  • Miles, K. C. (2013). Palladium-Catalyzed Carbocyclizations of Substituted Benzoic Acids and Tandem One-Pot Acyl Heck/Heck Coupling of Indanones [Master's thesis, Ohio State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=osu1377003454

    APA Style (7th edition)

  • Miles, Kelsey. Palladium-Catalyzed Carbocyclizations of Substituted Benzoic Acids and Tandem One-Pot Acyl Heck/Heck Coupling of Indanones. 2013. Ohio State University, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=osu1377003454.

    MLA Style (8th edition)

  • Miles, Kelsey. "Palladium-Catalyzed Carbocyclizations of Substituted Benzoic Acids and Tandem One-Pot Acyl Heck/Heck Coupling of Indanones." Master's thesis, Ohio State University, 2013. http://rave.ohiolink.edu/etdc/view?acc_num=osu1377003454

    Chicago Manual of Style (17th edition)

osu1377003454
187
© 2013, all rights reserved.
This open access ETD is published by The Ohio State University and OhioLINK.