Heterocycle-derived β-S-enals as bifunctional linchpins for the catalytic synthesis of saturated heterocycles

Literature Information

Publication Date 2016-03-23
DOI 10.1039/C6QO00057F
Impact Factor 5.281
Authors

Jingze Niu, Michael C. Willis


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Abstract

We demonstrate how heterocycle-derived β-S-enals can be employed as bifunctional substrates in a cascade of two rhodium-catalysed C–C bond forming reactions to deliver substituted heterocyclic products. A single rhodium-catalyst, generated in situ from a commercial salt and ligand combination, is used to promote both an initial alkene or alkyne hydroacylation reaction, and then a Suzuki-type cross-coupling, resulting in a three-component assembly of the targeted heterocycles. Substrates based on N-, O- and S-heterocycles are included, as are a range of alkenes, alkynes and boronic acid derivatives.

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Organic Chemistry Frontiers

Organic Chemistry Frontiers
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Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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