A multicomponent synthesis of stereodefined olefins via nickel catalysis and single electron/triplet energy transfer

Chen Zhu, Huifeng Yue, Bholanath Maity, Iuliana Atodiresei, Luigi Cavallo, Magnus Rueping

Research output: Contribution to journalArticlepeer-review

116 Scopus citations

Abstract

Unsaturated 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.
Original languageEnglish (US)
Pages (from-to)678-687
Number of pages10
JournalNature Catalysis
Volume2
Issue number8
DOIs
StatePublished - Jul 8 2019

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: The 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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