Publication

Three chloro(trifluoromethyl)pyridines as model substrates for regioexhaustive functionalization

Manfred Schlosser, Fabrice Cottet
2004
Journal Articles

Abstract

As a further test of the concept of regioexhaustive functionalization, 2-chloro-6-(trifluoromethyl)pyridine, 2-chloro-5-(trifluoromethyl)pyridine and 3-chloro-4-(trifluoromethyl)pyridine were each converted into the three possible carboxylic acids. This was achieved by employing several, but not all of the organometallic "toolbox methods"; transformation of a more basic organometallic species into a less basic isomer by transmetalation-equilibration, site discriminating deprotonation with lithium N,N-diisopropylamide or lithium 2,2,6,6-tetramethylpiperidide, regio-divergent iodine migration and steric screening of acidic positions by a bulky trialkylsilyl group. [on SciFinder (R)]

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https://infoscience.epfl.ch/entities/publication/32c766fb-8678-46a2-9f9c-cc80dce4b8e9

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Manfred Schlosser, Fabrice Cottet
2004
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/32c766fb-8678-46a2-9f9c-cc80dce4b8e9

About this result

Related concepts (15)

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.

Organometallic chemistry

Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and sometimes broadened to include metalloids like boron, silicon, and selenium, as well. Aside from bonds to organyl fragments or molecules, bonds to 'inorganic' carbon, like carbon monoxide (metal carbonyls), cyanide, or carbide, are generally considered to be organometallic as well.

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.

Related publications (1)

Three chloro(trifluoromethyl)pyridines as model substrates for regioexhaustive functionalization

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Fluoro- or trifluoromethyl-substituted benzyl and phenethyl alcohols: Substrates for metal-mediated site-selective functionalization