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Arynes in Synthesis;New Reaction and Precursor Development

Mcausland, Donald Euan Reynolds

[Thesis]. Manchester, UK: The University of Manchester; 2014.

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Abstract

The arylation of readily accessible N-tosyl hydrazones has been achieved using arynes generated in situ under mild conditions. The resulting N-tosyl-N-aryl hydrazones undergo a one-pot Fischer indole reaction on the addition of acid, giving a synthesis of protected indoles that avoids handling unstable intermediates and arylhydrazines.A new route to functionalised 2-(trimethylsilyl)phenyl triflate aryne precursors via Suzuki cross-coupling has been developed. The method allows the incorporation of a wide range of aryl and heteroaryl groups and reactions of arynes generated from these novel precursors have been demonstrated, including a cyclotrimerisation and a fluorenone synthesis.Work was also undertaken on aryne σ-insertion reactions. The addition of benzyne to ynamides was found to result in its net insertion between the nitrogen and acetylene species. The reaction proceeds from attack at the terminal carbon in an analogous manner to C(sp)–O insertions.