Publication

Regioselective ortho-lithiation of chloro- and bromo-substituted fluoroarenes

Manfred Schlosser
1996
Journal Articles

Abstract

Deprotonation of fluoroarenes carrying chlorine or bromine as addnl. substituents occurred always at a position adjacent to a fluorine if accomplished with potassium tert-butoxide activated butyllithium or lithium 2,2,6,6-tetramethylpiperidide. For example, treatment of 1-chloro-4-fluorobenzene with potassium tert-butoxide/butyllithium (superbase reagent) gave 5-chloro-2-fluorobenzoic acid (86% yield) as the major product and a small amt. of 2-chloro-5-fluorobenzoic acid. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/ba8f23b4-6429-4c31-b31a-73ab12e8f27f

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Manfred Schlosser
1996
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/ba8f23b4-6429-4c31-b31a-73ab12e8f27f

About this result

Related concepts (14)

Organolithium reagent

In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom to the substrates in synthetic steps, through nucleophilic addition or simple deprotonation. Organolithium reagents are used in industry as an initiator for anionic polymerization, which leads to the production of various elastomers.

Superbase

A superbase is a compound that has a particularly high affinity for protons. Superbases are of theoretical interest and potentially valuable in organic synthesis. Superbases have been described and used since the 1850s. Generically IUPAC defines a superbase as a "compound having a very high basicity, such as lithium diisopropylamide." Superbases are often defined in two broad categories, organic and organometallic. Organic superbases are charge-neutral compounds with basicities greater than that of proton sponge (pKBH+ = 18.

Arene substitution pattern

Arene substitution patterns are part of organic chemistry IUPAC nomenclature and pinpoint the position of substituents other than hydrogen in relation to each other on an aromatic hydrocarbon. Electrophilic aromatic substitution In ortho-substitution, two substituents occupy positions next to each other, which may be numbered 1 and 2. In the diagram, these positions are marked R and ortho. In meta-substitution the substituents occupy positions 1 and 3 (corresponding to R and meta in the diagram).