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Migratory Arylboration of Unactivated Alkenes Enabled by Nickel Catalysis
Ist Teil von
Angewandte Chemie International Edition, 2019-03, Vol.58 (14), p.4612-4616
Auflage
International ed. in English
Ort / Verlag
Germany: Wiley Subscription Services, Inc
Erscheinungsjahr
2019
Link zum Volltext
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
An unprecedented arylboration of unactivated terminal alkenes, featuring 1,n‐regioselectivity, has been achieved by nickel catalysis. The nitrogen‐based ligand plays an essential role in the success of this three‐component reaction. This transformation displays good regioselectivity and excellent functional‐group tolerance. In addition, the incorporation of a boron group into the products provides substantial opportunities for further transformations. Also demonstrated is that the products can be readily transformed into pharmaceutically relevant molecules. Unexpectedly, preliminary mechanistic studies indicate that although the metal migration favors the α‐position of boron, selective and decisive bond formation is favored at the benzylic position.
An unprecedented arylboration of unactivated terminal alkenes, featuring 1,n‐regioselectivity (n>2), has been achieved by nickel catalysis. An array of valuable alkylboronic esters are prepared with this method. Mechanism studies indicate that a nickel migration and a selective bond‐formation step are involved in this reaction.