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Tandem‐catalyzed hydroaminomethylation is a useful tool for synthesizing linear amines from olefins and amines in an atom‐efficient manner. To enable the coupling of highly functionalized, hydrosoluble amines with non‐water‐soluble olefins, this reaction must be transferred to aqueous biphasic solvent systems. In this work, we systematically evaluate reaction conditions to provide a selective hydroaminomethylation of 1‐octene with diethanolamine as model substrates. Although water is both the condensation side product and the solvent, yields of 79% were achieved using a catalytic system consisting a rhodium precursor and a sulfonated diphosphine ligand. This approach was applied to other functionalized amines, proving this concept is a suitable tool for the catalytic alkylation of highly functionalized amines.magnified image

Using the water-soluble N-methylglucamine and the non-polar β-myrcene in a biphasic telomerisation with the amphiphilic TPPMS ligand, new surfactants are obtained.

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