Nickel-Catalyzed Direct Alkenylation of Methyl Heteroarenes with Primary Alcohols.
J Org Chem
; 84(15): 9819-9825, 2019 Aug 02.
Article
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| MEDLINE
| ID: mdl-31262177
ABSTRACT
An efficient nickel-catalyzed acceptorless dehydrogenative coupling of methyl-substituted heteroarenes with primary alcohols is achieved using an in situ generated complex of inexpensive NiBr2 and readily available 8-aminoquinoline picolinic amide ligand. The protocol is operationally simple and scalable and furnishes a series of high-value 2-alkenylheteroarenes in good yields (up to 88%) with exclusive E-selectivity. The reaction proceeds with the release of water and molecular hydrogen, which was analyzed through gas chromatography to validate the reaction mechanism.
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2019
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Article