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Migratory Arylboration of Unactivated Alkenes Enabled by Nickel Catalysis
Author(s) -
Wang Wang,
Ding Chao,
Li Yangyang,
Li Zheqi,
Li Yuqiang,
Peng Long,
Yin Guoyin
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201814572
Subject(s) - regioselectivity , catalysis , nickel , chemistry , boron , functional group , ligand (biochemistry) , combinatorial chemistry , metal , molecule , group (periodic table) , organic chemistry , biochemistry , receptor , polymer
Abstract 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.