Gold-catalysed reactions of alkynyl sulfoxides

[摘要] 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.

[发布机构] University:University of Birmingham;Department:School of Chemistry

[关键词] Q Science;QD Chemistry