A multicomponent synthesis of stereodefined olefins via nickel catalysis and single electron/triplet energy transfer
KAUST DepartmentChemical Science
Chemical Science Program
KAUST Catalysis Center
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Embargo End Date2020-01-08
Permanent link to this recordhttp://hdl.handle.net/10754/656150
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AbstractUnsaturated carbon–carbon bonds are one of the most common and important structural motifs in many organic molecules, stimulating the continuous development of general, efficient and practical strategies for their functionalization. Here, we report a one-pot difunctionalization of alkynes via a photoredox/nickel dual-catalysed three-component cross-coupling reaction under mild conditions, providing access to a series of highly important tri-substituted alkenes. Notably, in contrast to traditional methods that are based on the steric hindrance of the substrates to control the reaction selectivity, both E- and Z-isomers of tri-substituted alkenes, which are often energetically close, can be obtained by choosing an appropriate photocatalyst with a suitable triplet state energy. Beyond the immediate practicality of this transformation, this newly developed methodology might inspire the development of diverse and important one-pot functionalizations of carbon–carbon multiple bonds via photoredox and transition-metal dual-catalysed multicomponent reactions.
CitationZhu, C., Yue, H., Maity, B., Atodiresei, I., Cavallo, L., & Rueping, M. (2019). A multicomponent synthesis of stereodefined olefins via nickel catalysis and single electron/triplet energy transfer. Nature Catalysis, 2(8), 678–687. doi:10.1038/s41929-019-0311-x
SponsorsThe authors thank D. Wöll and O. Nevskyi for assistance with measuring the emission spectra of the photocatalysts. H.Y. thanks the China Scholarship Council. C.Z., B.M., L.C. and M.R. acknowledge King Abdullah University of Science and Technology (KAUST) for support and the KAUST Supercomputing Laboratory for providing computational resources of the supercomputer Shaheen II. The research leading to these results has received funding from the European Research Council under the European Union’s Seventh Framework Programme (FP/2007-2013) and ERC grant agreement no. 617044 (SunCatChem).
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