A domino reaction for generating β-aryl aldehydes from alkynes by substrate recognition catalysis

Weiwei Fang, Felix Bauer, Yaxi Dong and Bernhard Breit ()
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Weiwei Fang: Albert-Ludwigs-Universität Freiburg
Felix Bauer: Albert-Ludwigs-Universität Freiburg
Yaxi Dong: Albert-Ludwigs-Universität Freiburg
Bernhard Breit: Albert-Ludwigs-Universität Freiburg

Nature Communications, 2019, vol. 10, issue 1, 1-9

Abstract: Abstract The development of universal catalyst systems that enable efficient, selective, and straightforward chemical transformations is of immense scientific importance. Here we develop a domino process comprising three consecutive reaction steps based on the strategy of supramolecular substrate recognition. This approach provides valuable β-aryl aldehydes from readily accessible α-alkynoic acids and arenes under mild reaction conditions, employing a supramolecular Rh catalyst containing an acylguanidine-bearing phosphine ligand. Furthermore, the synthesis of a key intermediate of Avitriptan using this protocol is accomplished. The first step of the reaction sequence is proved to be the regioselective hydroformylation of α-alkynoic acids. Remarkably, molecular recognition of the ligand and the substrate via hydrogen bonding plays a key role in this step. Control experiments indicate that the reaction further proceeds via 1,4-addition of an arene nucleophile to the unsaturated aldehyde intermediate and subsequent decarboxylation.

Date: 2019
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DOI: 10.1038/s41467-019-12770-w

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