Novel one-pot methods for the synthesis of heterocycles and functional aromatic compounds

Henry, Martyn Craig (2020) Novel one-pot methods for the synthesis of heterocycles and functional aromatic compounds. PhD thesis, University of Glasgow.

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Abstract

This PhD focused on the development of transition metal-catalysed one-pot processes for the rapid and selective formation of aryl C–N and C–O bonds from unactivated aryl C–H bonds. The key feature, common to all the processes, was the activation of aryl rings via a regioselective, iron triflimide-catalysed halogenation. After a brief description of a new iodination process in the first R&D section of this thesis, the second section details the development of a one-pot intermolecular aryl C–N bond forming process by copper-catalysed cross-coupling of in situ generated aryl iodides with unactivated N-nucleophiles.

The third section describes the extension of this methodology for the synthesis of indolines and 2,3-dihydrobenzofurans by intramolecular cross-coupling with pendant N- or O-nucleophiles. In addition to the synthesis of small libraries of heterocycles, this one-pot process was used as the key reaction in the 8-step total synthesis of neolignan natural product, (+)-obtusafuran.

The fourth and fifth sections detail the development of several one-pot processes for the synthesis of benzo[b]furans, benzoxazoles and benzothiazoles directly from the corresponding α-arylketones, N-arylbenzamides and N-arylthiobenzamides. Mechanistic insights as well as the synthesis of a range of biologically active heterocycles are presented.

Item Type: Thesis (PhD)
Qualification Level: Doctoral
Keywords: Organic chemistry, transition metal-catalysis, heterocycles, one-pot reactions
Subjects: Q Science > QD Chemistry
Colleges/Schools: College of Science and Engineering > School of Chemistry
Supervisor's Name: Sutherland, Dr. Andrew
Date of Award: 2020
Depositing User: Mr Martyn Craig Henry
Unique ID: glathesis:2020-81620
Copyright: Copyright of this thesis is held by the author.
Date Deposited: 01 Sep 2020 13:33
Last Modified: 01 Sep 2020 14:14
URI: http://theses.gla.ac.uk/id/eprint/81620
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