Divergent and Selective Light Alkene Cross-Coupling |
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Authors: | Zi-Chao Wang Jia-Wen Zhang Ming Joo Koh Shi-Liang Shi |
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Institution: | 1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 P. R. China;2. Department of Chemistry, National University of Singapore, 4 Science Drive 2, Singapore, 117544 Republic of Singapore |
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Abstract: | Light olefins are abundantly manufactured in the petroleum industry and thus represent ideal starting materials for modern chemical synthesis. Selective and divergent transformations of feedstock light olefins to value-added chemicals are highly sought-after but remain challenging. Herein we report an exceptionally regioselective carbonickelation of light alkenes followed by in situ trapping with three types of nucleophiles, namely a reductant, base, or Grignard reagent. This protocol enables efficient 1,2-hydrofunctionalization, dicarbofunctionalization, and branched-selective Heck-type cross-coupling of light alkenes with aryl and alkenyl reagents to streamline access to diverse alkyl arenes and complex alkenes. Harnessing bulky N-heterocyclic carbene ligands with acenaphthyl backbones for nickel catalysts is crucial to attain high reactivity and selectivity. This strategy provides a rare, modular, and divergent platform for upgrading feedstock alkenes and is expected to find broad applications in medicinal chemistry and industrial processes. |
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Keywords: | Carbonickelation Cross-Coupling Light Alkene N-Heterocyclic Carbene Nickel Catalysis |
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