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Published on: August 16, 2018
Manganese-Catalyzed Aromatic C-H Allylation of Ketones
Shaukat Ali1, Jiaqi Huo1,2, Congyang Wang1,2,3
1Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China.
Abstract:
Manganese-catalyzed aromatic C-H allylation of ketones is reported. The reaction proceeded in a monoselective allylation manner to provide various ortho C-H allylated ketones in high yields. With challenging allylic electrophiles bearing substituents at the α-, β-, or γ-position, excellent SN2' regioselectivity was achieved under mild conditions (rt to 35 °C). Mechanistic studies revealed a possible turnover-limiting C-H bond cleavage step affording a five-membered manganacycle followed by reaction with allylic electrophiles to give the C-H allylation product.
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