Alkenyl arenes are used on a large scale as building blocks for plastics, elastomers, fine chemicals, and surfactants. Alkenyl arenes are produced by arene alkylation with acid-based catalysis using Friedel Crafts alkylation or acidic zeolites followed by a dehydrogenation step. These methods use harsh acids, high temperatures, and produce only or predominantly the Markovnikov product (for reactions with substituted olefins) due to the carbocation intermediate from the electrophilic aromatic substitution mechanism. Transition metal based oxidative hydroarylation of olefins can produce anti-Markovnikov products. Here, we show a Rh(I) complex, [Rh(η2-C2H4)(μ-OAc)2]2 and an Ir(I) complex, [Ir(μ-Cl)(COE)2]2 are catalysts for the oxidative hydrophenylation of ethylene and propylene in the presence of Cu(II) salts. The rate of reaction and selectivity of anti-Markovnikov and Markovnikov products will be further examined. This presentation will focus on the comparison of Rh(I) and Ir(I) catalyzed arene alkenylation.

Arene alkenylation using Rh(I) and Ir(I) catalysts

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ACS Fall 2022

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