<br/>The selective catalytic functionalization of C–H bonds of hydrocarbons remains one of the foremost challenges facing synthetic chemists. Processes that convert C–H bonds of simple hydrocarbons into new C–C bonds are particularly important. For example, alkyl and alkenyl arenes are currently produced on a scale of billions of pounds per year, and the addition of aromatic C–H bonds across olefin C=C bonds, olefin hydroarylation, provides an atom economical reaction with broad potential including applications in both commodity scale processes as well as fine chemical synthesis. Current industrial catalysts (e.g., Friedel-Crafts catalysis or zeolites) for arene alkylation are based on acid-mediated olefin activation. New catalysts that operate by an entirely different pathway that involves transition metal-mediated C–H activation followed by olefin insertion into metal-aryl bonds offer new opportunities including the ability 1) to generate alkenyl arenes in a single step using air or air-recyclable oxidants, 2) to prepare 1-substituted aryl alkanes (or alkenyl precursors), 3) to alkylate or alkenylate electron-deficient arenes, and 4) to access new regioselectivities for alkylation or alkenylation of substituted arenes. This presentation will focus on progress toward the development and understanding of catalysts based on Ru, Pd, Pt and Rh for arene alkylation and alkenylation with a primary focus on new Rh-based catalysts that provide long-lived and highly selective processes.

Transition metal catalyzed hydroarylation of olefins: New catalysts for alkyl and alkenyl arenes

ACS Spring 2022

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