Reductive lithiation of alkyl phenyl sulfides in diethyl ether. A ready access to α,α-dialkylbenzyllithiums
@article{Screttas2003ReductiveLO, title={Reductive lithiation of alkyl phenyl sulfides in diethyl ether. A ready access to α,α-dialkylbenzyllithiums}, author={C. Screttas and Georgios A. Heropoulos and Maria Micha-Screttas and B. Steele and D. Catsoulacos}, journal={Tetrahedron Letters}, year={2003}, volume={44}, pages={5633-5635} }
Diethyl ether is a convenient solvent for the conversion of benzylic phenyl sulfides to the corresponding organolithiums by an uncatalyzed reductive metalation, while catalysis by naphthalene is required to achieve the same reaction for alkyl phenyl sulfides. The addition of magnesium 2-ethoxyethoxide to solutions of unstable alkyllithiums prepared in this way provides storable reagents.
11 Citations
A general palladium-catalyzed coupling of aryl bromides/triflates and thiols.
- Chemistry, Medicine
- Organic letters
- 2004
- 331
- PDF
Aryllithiums with increasing steric crowding and lipophilicity prepared from chlorides in diethyl ether. The first directly prepared room-temperature-stable dilithioarenes.
- Chemistry, Medicine
- Organic letters
- 2012
- 14
Beyond benzyl grignards: facile generation of benzyl carbanions from styrenes.
- Chemistry, Medicine
- Chemistry
- 2012
- 25
Reductive Lithiation in the Absence of Aromatic Electron Carriers. A Steric Effect Manifested on the Surface of Lithium Metal Leads to a Difference in Relative Reactivity Depending on Whether the Aromatic Electron Carrier Is Present or Absent.
- Chemistry, Medicine
- The Journal of organic chemistry
- 2015
- 4
Techno-Economic Analysis of Magnesium Extraction from Seawater via a Catalyzed Organo-Metathetical Process
- Materials Science
- 2018
- 3
Carbon-carbon bond-forming reactions of α-thioaryl carbonyl compounds for the synthesis of complex heterocyclic molecules.
- Chemistry, Medicine
- The Journal of organic chemistry
- 2012
- 13
- PDF
References
SHOWING 1-10 OF 13 REFERENCES
Stoicheiometry and synthetic utility of the reaction of alkyl halides with lithium dihydronaphthylide
- Chemistry
- 1972
- 17
Ortho-Directed Lithiation of omega-Phenoxy Alcohols.
- Chemistry, Medicine
- The Journal of organic chemistry
- 1999
- 12
Use of aromatic radical-anions in the absence of THF. Tandem formation and cyclization of benzyllithiums derived from the attack of homo- and bishomoallyllithiums on alpha-methylstyrenes: two-pot synthesis of cuparene.
- Chemistry, Medicine
- Journal of the American Chemical Society
- 2001
- 32
- PDF