Publication

Strategies for the selective functionalization of dichloropyridines at various sites

Manfred Schlosser
2001
Journal Articles

Abstract

Whereas 2,3-dichloropyridine and 2,5-dichloro-4-(lithiooxy)pyridine undergo deprotonation exclusively at the 4- and 2-positions, resp., optional site selectivity can be implemented with 2,5- and 3,4-dichloropyridine (which are attacked, depending on the choice of the reagents, at either the 4- or 6- and either the 2- or 5-positions, resp.). Upon treatment with lithium diisopropylamide, 2,4-dichloro-3-iodopyridine, 3,5-dichloro-4-bromopyridine, and 2,6-dichloro-3-iodopyridine afford 5-, 2-, and 4-lithiated intermediates, but the latter isomerize instantaneously to species in which lithium and iodine have swapped places, the driving force being the low basicity of C-Li bonds when flanked by two neighboring halogens. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/d569eb77-a3a5-4ae9-853a-858f7fa3b797

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Manfred Schlosser
2001
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/d569eb77-a3a5-4ae9-853a-858f7fa3b797

About this result

Related concepts (16)

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.

Indole

Indole is an aromatic, heterocyclic, organic compound with the formula . It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered pyrrole ring. Indole is widely distributed in the natural environment and can be produced by a variety of bacteria. As an intercellular signal molecule, indole regulates various aspects of bacterial physiology, including spore formation, plasmid stability, resistance to drugs, biofilm formation, and virulence.

N-Butyllithium

n-Butyllithium C4H9Li (abbreviated n-BuLi) is an organolithium reagent. It is widely used as a polymerization initiator in the production of elastomers such as polybutadiene or styrene-butadiene-styrene (SBS). Also, it is broadly employed as a strong base (superbase) in the synthesis of organic compounds as in the pharmaceutical industry. Butyllithium is commercially available as solutions (15%, 25%, 1.5 M, 2 M, 2.5 M, 10 M, etc.) in alkanes such as pentane, hexanes, and heptanes.