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Remote C−H functionalization using radical translocating arylating groups

Author

Listed:
  • Florian W. Friese

    (Westfälische Wilhelms-Universität)

  • Christian Mück-Lichtenfeld

    (Westfälische Wilhelms-Universität
    Center for Multiscale Theory and Computation (CMTC))

  • Armido Studer

    (Westfälische Wilhelms-Universität)

Abstract

Site selective chemical functionalization at unactivated C(sp3)−H bonds is highly challenging and recent successful studies mostly focus on the use of transition metal catalysis in combination with directing groups. Radical chemistry offers a complementary approach with the Barton and the Hofmann-Löffler-Freytag reactions being landmark contributions in the area of remote C−H functionalization at unactivated aliphatic sites. Herein we introduce the concept of radical translocation arylation at unactivated secondary and tertiary C(sp3)−H bonds in various alcohols. The straightforward two-step sequence comprises an ionic alcohol sulfonylation with especially designed ortho-iodoaryl sulfonyl chlorides followed by a radical cascade reaction including aryl radical generation, remote radical translocation, aryl migration, reduction, and SO2 extrusion to give the corresponding γ-arylated alcohols. Moderate to good yields are obtained, remote C−H arylation occurs with excellent regioselectivity and for secondary C(sp3)−H bonds good to excellent stereoselectivity is achieved.

Suggested Citation

  • Florian W. Friese & Christian Mück-Lichtenfeld & Armido Studer, 2018. "Remote C−H functionalization using radical translocating arylating groups," Nature Communications, Nature, vol. 9(1), pages 1-7, December.
  • Handle: RePEc:nat:natcom:v:9:y:2018:i:1:d:10.1038_s41467-018-05193-6
    DOI: 10.1038/s41467-018-05193-6
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