Mura, Manuel Giacomo (2015) Hydrogen transfer methods in organic synthesis. Doctoral Thesis.
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In recent years, there has been an increasing interest in using alcohols and amines as starting materials in chemical synthesis because they are an environmentally friendly and renewable alternative to petroleum-based products. The work illustrated in the present thesis focuses on the development of new synthetic methodologies exploiting hydrogen transfer as activation strategy that consents the use of alcohols and amines as starting materials to prepare molecules of industrial and pharmaceutical interest.
Given the high importance of heterocycles in several fields of chemistry and technology, we gave great focus on privileged structures such as indoles. A new and efficient strategy for indole synthesis via a Ru-catalysed cross-coupling of arylhydrazines with alcohols has been developed. Our method represents the first example for indole synthesis starting from alcohols via a Fischer-type reaction. In a complementary work, we investigated the use of primary amines as pro-electrophiles in the synthesis of indoles using Pd/C as a heterogeneous catalyst. Exploiting the know-how acquired in hydrogen transfer strategies, we turned our attention on the synthesis of α,β-unsaturated aldehydes through a Ru-catalysed cross-dehydrogenative coupling between two different primary alcohols, which can find potential application in the preparation of jasminaldehyde and its analogues, largely used in the fragrance industries. We also extended this strategy to the synthesis of quinolines.
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