Publication

Regioflexibility in the functionalization of multiply halogenated quinolines

Manfred Schlosser
2004
Journal Articles

Abstract

4-Bromo-6-fluoro-2-(trifluoromethyl)quinoline and 4-bromo-7-fluoro-2-(trifluoromethyl)quinoline were selected as model substrates to explore under what conditions regiochem. exhaustive functionalization reactions can be carried out. This goal was achieved by using trimethylsilyl entities and iodine atoms as the sole auxiliary substituents. The organolithium intermediates could be generated and the protective groups removed without impairing the bromine atom present at the 4-position. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/f6ae3a96-e8e5-45bc-8cbe-321d13e3f072

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Manfred Schlosser
2004
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/f6ae3a96-e8e5-45bc-8cbe-321d13e3f072

About this result

Related concepts (22)

Iodine

Iodine is a chemical element with the symbol I and atomic number 53. The heaviest of the stable halogens, it exists as a semi-lustrous, non-metallic solid at standard conditions that melts to form a deep violet liquid at , and boils to a violet gas at . The element was discovered by the French chemist Bernard Courtois in 1811 and was named two years later by Joseph Louis Gay-Lussac, after the Ancient Greek Ιώδης 'violet-coloured'. Iodine occurs in many oxidation states, including iodide (I−), iodate (IO3-), and the various periodate anions.

Bromine

Bromine is a chemical element with the symbol Br and atomic number 35. It is a volatile red-brown liquid at room temperature that evaporates readily to form a similarly coloured vapour. Its properties are intermediate between those of chlorine and iodine. Isolated independently by two chemists, Carl Jacob Löwig (in 1825) and Antoine Jérôme Balard (in 1826), its name was derived from the Ancient Greek βρῶμος (bromos) meaning "stench", referring to its sharp and pungent smell.

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.