Development of novel transition metal-catalyzed cross-coupling reactions and applications thereof
Name
861616258-MIT.pdf
Description
Full printable version
Size
9.86 MB
Format
Adobe PDF
Checksum (MD5)
2cee72d6321c2f30154d43f64990904d
Author(s)
Teverovskiy, Georgiy
Advisor(s)
Stephen L. Buchwald.
Date Issued
2013
Publisher
Massachusetts Institute of Technology
Abstract
Chapter 1 The first example of Pd(0)/(II) catalyzed fluorination of aryl bromides is reported herein. Based on these data, an analogous method was developed for the fluorination of aryl triflates. The reaction proceeds under mild conditions and represents the first report of reductive elimination from a Pd(II) center of a C-F bond. Chapter 2 Herein we report the first example of a Pd-catalyzed synthesis of aryl trifluoromethyl sulfides. A wide range of aryl bromides are converted to their corresponding trifluoromethyl sulfides in good to excellent yields. Furthermore, we were successful in synthesizing an intermediate in the synthesis of Toltrazuril in two steps from commercially available starting materials. Chapter 3 The development of a novel precatalyst for Ni-catalyzed C-N bond formation is described herein. Furthermore, the substrate scope of the reaction has been expanded to include a wide range of nucleophiles and electrophiles. Finally, we report the first use of weak base in the Nicatalyzed arylation of anilines. Chapter 4 The development of a novel triptycene-based hole-transport material is reported. Computational as well as preliminary photophysical and voltammetric data suggests that this class of compounds could serve as an excellent host material for blue triplet emitters.
Description
Thesis (Ph. D. in Organic Chemistry)--Massachusetts Institute of Technology, Dept. of Chemistry, 2013.
Cataloged from PDF version of thesis.
Includes bibliographical references.
Subjects
Chemistry.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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