Arene-catalysed lithiation reactions with lithium at low temperature
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 6,p. 398-400
- https://doi.org/10.1039/c39910000398
Abstract
The reaction of functionalized alkyl chlorides or phenyl sulphides with an excess of lithium powder in the presence of a catalytic amount of an arene (1%; naphthalene, biphenyl, 4,4′-di-tert-butylbiphenyl) in tetrahydrofuran (THF) at –78 °C gives the corresponding organolithium compounds, which react with electrophiles such as water, iso-butyraldehyde, or cyclohexanone to yield the expected reaction products.Keywords
This publication has 17 references indexed in Scilit:
- Organocalcium chemistry: preparation and reactions of highly reactive calciumThe Journal of Organic Chemistry, 1990
- 2-(3-Lithiopropyl)- and 2-(3-lithiopropyl)-2-methyl-1,3-dioxolane: New masked lithium bishomoenolates in the synthesis of bifunctionalized compoundsTetrahedron Letters, 1990
- Organoalkali compounds by radical anion induced reductive metalation of phenyl thioethersAccounts of Chemical Research, 1989
- N-lithio-n-(2-lithioethyl)benzamide: direct preparation of a 2-lithioethylamine equivalentTetrahedron Letters, 1988
- 3,3-Diethoxypropyl-lithium: a masked lithium propanal homoenolateJournal of the Chemical Society, Chemical Communications, 1987
- Stereochemistry of the reactions of lithium di-tert-butylbiphenyl with alkyl halidesThe Journal of Organic Chemistry, 1983
- β-Substituted organolithium compounds; direct preparation and reactivityJournal of the Chemical Society, Chemical Communications, 1982
- Reductive Lithiation of Some Thioketals Using Lithium 1-(Dimethylamino)naphthalenideSynthetic Communications, 1980
- Hydrolithiation of .alpha.-olefins by a regiospecific two-step process. Transformation of alkyl phenyl sulfides to alkyllithium reagentsThe Journal of Organic Chemistry, 1978
- Reactions of the radical anions and dianions of aromatic hydrocarbonsChemical Reviews, 1974