Premium
Highly Regioselective Remote Lithiation of Functionalized 1,3‐bis‐Silylated Arenes
Author(s) -
Bellan Andreas B.,
Knochel Paul
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.201812742
Subject(s) - regioselectivity , silylation , electrophile , chemistry , pyridine , biphenyl , medicinal chemistry , reactivity (psychology) , organic chemistry , catalysis , medicine , alternative medicine , pathology
Substituted arenes flanked by two bulky triethylsilyl groups were regiospecifically lithiated at the 5‐position with nBuLi⋅PMDTA at 25 °C. The resulting aryllithiums reacted with a broad range of electrophiles such as ketones, isocyanates, Weinreb amides, allyl bromides, and CO 2 at 25 °C. These bis‐silylated arenes were then converted in simple reaction sequences into silyl‐free tetrasubstituted arenes. This remote lithiation was extended to 2,6‐bis(triethylsilyl)pyridine as well as 3,3′‐bis(triethylsilyl)biphenyl.