Publication

Halogen shuffling in pyridines: site selective electrophilic substitutions of 2-chloro-6-(trifluoromethyl)pyridine

Manfred Schlosser, Fabrice Cottet
1998
Journal Articles

Abstract

When treated with lithium diisopropylamide in THF at -85 Deg and subsequently with iodine, 2-chloro-6-(trifluoromethyl)pyridine is neatly converted into its 3-iodo deriv. The latter can be quant. isomerized to afford 2-chloro-4-iodo-6-(trifluoromethyl)pyridine. Either iodo compd. can serve as the starting material for further manipulation in reaction sequences consisting of halogen/metal exchange and electrophilic trapping. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/4537b013-154b-44f3-9aa6-db884ee332d4

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Manfred Schlosser, Fabrice Cottet
1998
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/4537b013-154b-44f3-9aa6-db884ee332d4

About this result

Related concepts (19)

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.

Metal–halogen exchange

In organometallic chemistry, metal–halogen exchange is a fundamental reaction that converts an organic halide into an organometallic product. The reaction commonly involves the use of electropositive metals (Li, Na, Mg) and organochlorides, bromides, and iodides. Particularly well-developed is the use of metal–halogen exchange for the preparation of organolithium compounds. Two kinds of lithium–halogen exchange can be considered: reactions involving organolithium compounds and reactions involving lithium metal.

Transmetalation

Transmetalation (alt. spelling: transmetallation) is a type of organometallic reaction that involves the transfer of ligands from one metal to another. It has the general form: M1–R + M2–R′ → M1–R′ + M2–R where R and R′ can be, but are not limited to, an alkyl, aryl, alkynyl, allyl, halogen, or pseudohalogen group. The reaction is usually an irreversible process due to thermodynamic and kinetic reasons. Thermodynamics will favor the reaction based on the electronegativities of the metals and kinetics will favor the reaction if there are empty orbitals on both metals.

Related publications (2)

Halogen shuffling in pyridines: site selective electrophilic substitutions of 2-chloro-6-(trifluoromethyl)pyridine

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3-Amino-2-arylpropanoic acids by electrophilic substitution of 2-arylethylamines at the benzylic position

Selective syntheses with organometallics. 7. (Z)-2-Ethoxyvinyllithium: a remarkably stable and synthetically useful 1,2-counterpolarized species