394-30-9Relevant articles and documents
Design and application of a low-temperature continuous flow chemistry platform
Newby, James A.,Blaylock, D. Wayne,Witt, Paul M.,Pastre, Julio C.,Zacharova, Marija K.,Ley, Steven V.,Browne, Duncan L.
, p. 1211 - 1220 (2014/12/10)
A flow reactor platform technology applicable to a broad range of low temperature chemistry is reported. The newly developed system captures the essence of running low temperature reactions in batch and represents this as a series of five flow coils, each with independently variable volume. The system was initially applied to the functionalization of alkynes, Grignard addition reactions, heterocycle functionalization, and heteroatom acetylation. This new platform has then been used in the preparation of a 20-compound library of polysubstituted, fluorine-containing aromatic substrates from a sequential metalation-quench procedure and can be readily adapted to provide gaseous electrophile inputs such as carbon dioxide using a tube-in-tube reactor.
Fluorine as an ortho-directing group in aromatic metalation: Generality of the reaction and the high position of fluorine in the Dir-Met potency scale
Bridges,Lee,Maduakor,Schwartz
, p. 7495 - 7498 (2007/10/02)
Many para-substituted fluorobenzenes can be lithiated ortho to fluorine in moderate to good yields, often with one of the dialkylamide bases, lithium diisopropylamide (LDA) or lithium 2,2,6,6-tetramethylpiperidide (LiTMP). Intramolecular competition experiments reveal that fluorine is one of the most potent Dir-Met activating groups under these conditions.
