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Abstract

In Chapter 2, a gold-catalyzed reaction of a bromoalkyne with anthranils to synthesis α-ketoamides is covered. In this reaction, two equivalents nitrene are used to functionalize a C-C triple bond by gold catalysis. Subsequently one equivalent nitrene remains in the amide function of the desired product, while the other equivalent of nitrene is eliminated during the hydrolysis process as an amine. This particular hydrolysis of the intermediate α-iminoimidoyl halides opens access to α-ketoamides for a wide range of haloalkynes. In Chapter 3, a one-step gold-catalyzed hydroamination of alkynes with hydroxylamine-O-sulfonic acid (HOSA) is reported. In this reaction, the limits that traditional synthesis of oximes is highly dependent on carbonyl compounds, is overcome, which expands the diversity of accessible oximes. Green chemistry metrics for this facile reaction are also calculated, this process shows 100% carbon efficiency.