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Multimetallic catalysed radical oxidative C(sp3)–H/C(sp)–H cross-coupling between unactivated alkanes and terminal alkynes

Author

Listed:
  • Shan Tang

    (College of Chemistry and Molecular Sciences, Institute for Advanced Studies (IAS), Wuhan University)

  • Pan Wang

    (College of Chemistry and Molecular Sciences, Institute for Advanced Studies (IAS), Wuhan University)

  • Haoran Li

    (College of Chemistry and Molecular Sciences, Institute for Advanced Studies (IAS), Wuhan University)

  • Aiwen Lei

    (College of Chemistry and Molecular Sciences, Institute for Advanced Studies (IAS), Wuhan University
    National Research Center for Carbohydrate Synthesis, Jiangxi Normal University)

Abstract

Radical involved transformations are now considered as extremely important processes in modern organic synthetic chemistry. According to the demand by atom-economic and sustainable chemistry, direct C(sp3)–H functionalization through radical oxidative coupling represents an appealing strategy for C–C bond formations. However, the selectivity control of reactive radical intermediates is still a great challenge in these transformations. Here we show a selective radical oxidative C(sp3)–H/C(sp)–H cross-coupling of unactivated alkanes with terminal alkynes by using a combined Cu/Ni/Ag catalytic system. It provides a new way to access substituted alkynes from readily available materials. Preliminary mechanistic studies suggest that this reaction proceeds through a radical process and the C(sp3)–H bond cleavage is the rate-limiting step. This study may have significant implications for controlling selective C–C bond formation of reactive radical intermediates by using multimetallic catalytic systems.

Suggested Citation

  • Shan Tang & Pan Wang & Haoran Li & Aiwen Lei, 2016. "Multimetallic catalysed radical oxidative C(sp3)–H/C(sp)–H cross-coupling between unactivated alkanes and terminal alkynes," Nature Communications, Nature, vol. 7(1), pages 1-8, September.
    • Handle: RePEc:nat:natcom:v:7:y:2016:i:1:d:10.1038_ncomms11676
    DOI: 10.1038/ncomms11676
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