Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 14, Pages 5738-5746Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201914061
Keywords
alkynes; arylalkylation; DFT calculations; hydroalkylation; nickel; photoredox reactions
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Funding
- King Abdullah University of Science and Technology (KAUST)
- European Research Council under the European Union's Seventh Framework Programme (FP/2007-2013)/ERC [617044]
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Alkynes are an important class of organic molecules due to their utility as versatile building blocks in synthesis. Although efforts have been devoted to the difunctionalization of alkynes, general and practical strategies for the direct hydroalkylation and alkylarylation of terminal alkynes under mild reaction conditions are less explored. Herein, we report a photoredox/nickel dual-catalyzed anti-Markovnikov-type hydroalkylation of terminal alkynes as well as a one-pot arylalkylation of alkynes with alkyl carboxylic acids and aryl bromides via a three-component cross-coupling. The results indicate that the transformations proceed via a new mechanism involving a single-electron transfer with subsequent energy-transfer activation pathways. Moreover, steady-state and time-resolved fluorescence-spectroscopy measurements, density functional theory (DFT) calculations, and wavefunction analysis have been performed to give an insight into the catalytic cycle.
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