Catalytic Hydroarylation of Alkynes
Summary
Catalytic hydroarylation of alkynes describes the addition of an aryl C–H bond across a carbon–carbon triple bond to form substituted alkenes in a single step. This transformation offers high atom economy and streamlines the synthesis of fine chemicals, pharmaceuticals and advanced materials. Key mechanistic pathways include electrophilic activation of the alkyne, oxidative addition of the aryl C–H bond, carbometallation to generate an alkenyl–metal intermediate and reductive elimination to yield the hydroarylation product. Advances in ligand design, catalyst selection and reaction conditions have addressed longstanding challenges in regioselectivity, enantioselectivity and functional-group tolerance. Recent emphasis on earth-abundant metal catalysts, photochemical activation and dual-catalytic systems has broadened the substrate scope and improved sustainability, positioning hydroarylation as a versatile tool for complex molecule assembly.
Research from Nature Portfolio
Recent studies have introduced a nickel–phosphine system enabling enantioselective hydroarylation under mild conditions, achieving high stereocontrol across a broad array of internal and terminal alkynes, including heterocyclic substrates. Mechanistic investigations highlighted an alkenyl–nickel intermediate as the stereodetermining species. Another report described a visible-light-mediated dual photoredox–palladium approach, facilitating hydroarylation of unactivated alkynes at ambient temperature without strong acids, exemplifying a shift towards sustainable, low-energy protocols. A further advance employed a copper-catalysed tandem hydroarylation strategy to construct complex polycyclic frameworks in a single operation, demonstrating rapid assembly of intricate molecular architectures.
Catalytic Hydroarylation of Alkynes publication trend
The graph below shows the total number of articles in catalytic hydroarylation of alkynes across all publications each year (not limited to Nature Index journals).
Technical terms
Hydroarylation: Addition of an aryl C–H bond across an unsaturated carbon–carbon bond.
Alkyne: A hydrocarbon containing at least one carbon–carbon triple bond.
Catalyst: A substance that increases the rate of a chemical reaction without being consumed.
Regioselectivity: Preference for bond formation at one position over others in a substrate.
Enantioselectivity: Preference for formation of one enantiomer over its mirror image in a chiral product.
C–H activation: Process of breaking a carbon–hydrogen bond to form a new bond with a metal centre.
References
- Alkyne hydroarylation with Au N-heterocyclic carbene catalysts. Beilstein Journal of Organic Chemistry (2013).
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