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Hydroformylation is a consolidated synthetic tool in the chemical industry, both in the commodity and in the fine chemicals segments. Olefin metathesis has been largely employed in the petrochemical sector,...

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2-Arylpropylamines are useful as active pharmaceutical ingredients (APIs) and as synthetic building blocks in fine chemistry. Herein we report a new and efficient methodology to transform naturally occurring 1-propenylbenzenes into 2-arylpropylamines employing a one-pot ethenolysis/hydroaminomethylation protocol. Four consecutive reactions must occur in the same reaction vessel and the careful selection of the reaction conditions was critical to obtain the desired products in high yields. The negative interference between the ethenolysis and the hydroaminomethylation (HAM) catalysts was circumvented by the appropriate adjustment on the molar ratio of the catalysts. As a result, nine 2-arylpropylamines were obtained in yields ranging in 75-93 %.

Hydroaminomethylation (HAM) is a tandem catalytic process that allows accessing amines from olefin scaffolds and is perfectly aligned with green chemistry precepts. In this work, HAM was applied to the natural hydroxyolefins: isoprenol, linalool, nerolidol, and isopulegol. Employing 4‐methylpiperidine, morpholine, and 1,2,3,4‐tetrahydroisoquinoline as counterparts, several new, structurally complex amines were prepared from biorenewable, low‐cost substrates, opening a path to exploit this structure diversity in biological activity. By the appropriate choice of rhodium‐based catalytic systems, as well as the reaction conditions, the necessary fine tuning for each counterpart was achieved. The unpromoted rhodium system leaded mostly to aminoalcohols, while certain phosphorus(III)‐promoted rhodium systems afforded amines containing a tetrahydropyran or a tetrahydrofuran moiety in moderate to high yields.

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