Remote C−H functionalization using radical translocating arylating groups

Florian W. Friese, Christian Mück-Lichtenfeld and Armido Studer ()
Additional contact information
Florian W. Friese: Westfälische Wilhelms-Universität
Christian Mück-Lichtenfeld: Westfälische Wilhelms-Universität
Armido Studer: Westfälische Wilhelms-Universität

Nature Communications, 2018, vol. 9, issue 1, 1-7

Abstract: 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.

Date: 2018
References: Add references at CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/s41467-018-05193-6 Abstract (text/html)

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:9:y:2018:i:1:d:10.1038_s41467-018-05193-6

Ordering information: This journal article can be ordered from
https://www.nature.com/ncomms/

DOI: 10.1038/s41467-018-05193-6

Access Statistics for this article

Nature Communications is currently edited by Nathalie Le Bot, Enda Bergin and Fiona Gillespie

More articles in Nature Communications from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().