In the query to synthesize bioactive natural compounds and functional materials, benzene derivatives are important intermediates. In cases, when the necessary benzene core's modification may not be reached using substitution, other methods have to be used. Among others, the domino Diels-Alder/retro-Diels-Alder (DA/RDA) reaction of a-2H-pyranones or 1,2-diazines are attractive processes in this respect. To the best of our knowledge, the corresponding transformation of analogous d-sultones embedding a 1,3-diene moiety, the sulfonic acid analog to a-2H-pyranones, was unknown.We synthesised a variety of phenylic substituted 1,3-dienic d-sultones,1,2 which had the potential to perform a Diels-Alder/retro-Diels-Alder reaction. Here, we show the potential of this reaction, by using sultones 2-4  with a variety of functionalized arylic residues (Figure 1A).3,4 We are very positive about the outcome of the reactions, as an X-Ray crystal structure was available for one structure of 2  , 3  and 6  .The de novo benzene synthesis of terphenyl derivatives 6a-6g  could be achieved with sultones 2a  -2g  , using a Diels-Alder/retro Diels-Alder approach with DMAD 5  as a dienophile (Figure 1B). In case of monosubstituted alkynes, 1,3,5 substituted terphenyls were formed almost exclusively. For all reactants investigated, microwave radiation proved to be the most efficient way to perform the reaction, while high pressure activation showed to be the cleanest way.2,4We therefore showed that 1,3-dienic Sultones can be transformed into terphenyls using a DA/RDA approach.

De novo benzene Ring synthesis using novel 1,3-dienic-d-sultones using a Diels-Alder/retro-Diels-Alder strategy

248th National Meeting (2014)

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