# Gold-catalysed reactions of alkynyl sulfoxides

Khan, Ghulam Fatima (2016). Gold-catalysed reactions of alkynyl sulfoxides. University of Birmingham. M.Sc.

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## Abstract

Gold π-catalysis has been used to overcome many challenges in synthesis, either by achieving complexity over few steps or providing a means to access formerly elusive functionality. This thesis details the development of a gold-catalysed reaction of alkynyl sulfoxides. The reaction of these 1,6-enynes proceeds $$via$$ an intramolecular oxidative [2+1] cycloaddition. These transformations gave a range of novel, isolable thiabicyclo[3.1.0]hexanes. This previously unreported methodology gives rise to a new way of synthesising heterocycles but also proceeds $$via$$ a carbenoid centre adjacent to a sulfoxide moiety – this combination of functionality is the first of its kind in acyclic systems – opening up a new class of α-carbenoid sulfoxides. The same functionality has not been achieved using classical approaches. Optimisation of the reaction was performed. The conditions were then applied to a range of alkynyl sulfoxides to explore their reaction profiles.

Type of Work: Thesis (Masters by Research > M.Sc.)
Award Type: Masters by Research > M.Sc.
Supervisor(s):
Supervisor(s)EmailORCID
Davies, PaulUNSPECIFIEDUNSPECIFIED
Grainger, Richard S.UNSPECIFIEDUNSPECIFIED
Licence:
College/Faculty: Colleges (2008 onwards) > College of Engineering & Physical Sciences
School or Department: School of Chemistry
Funders: None/not applicable
Subjects: Q Science > QD Chemistry
URI: http://etheses.bham.ac.uk/id/eprint/6586

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