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Reactivity of tert-butanesulfinamides in palladium-catalyzed allylic substitutions
- Source :
- Journal of Organometallic Chemistry, Journal of Organometallic Chemistry, Elsevier, 2014, 760, pp.124--129. ⟨10.1016/j.jorganchem.2013.11.026⟩, Journal of Organometallic Chemistry, Elsevier, 2014, 760, pp.124--129. 〈10.1016/j.jorganchem.2013.11.026〉, Journal of Organometallic Chemistry, 2014, 760, pp.124--129. ⟨10.1016/j.jorganchem.2013.11.026⟩
- Publication Year :
- 2014
- Publisher :
- Elsevier BV, 2014.
-
Abstract
- The performance of tert-butanesulfinamides as nitrogen nucleophiles in Pd(0)-catalyzed allylic substitution reactions has been investigated. Metalated N-alkyl and N-acetyl sulfinamides have been identified as suitable partners for the reaction with π-allyl–palladium complexes. The cross-coupling of N-acetyl tert-butanesulfinamide with 2- or 3-substituted linear allylic carbonates is achieved in the presence of Pd(OAc)2 (5 mol%) and dppe (7.5 mol%) and does not require an additional base. The reaction proceeds in high yields (59–98%) to produce the corresponding E-configured linear allylic sulfinamides in a totally regioselective and highly diastereoselective manner. The sulfur atom remains configurationally stable throughout the allylation process, and thus the coupling products are obtained in enantiomerically pure form.
- Subjects :
- Substitution reaction
Allylic rearrangement
Chemistry
Organic Chemistry
Regioselectivity
chemistry.chemical_element
[ CHIM ] Chemical Sciences
Biochemistry
Medicinal chemistry
Inorganic Chemistry
chemistry.chemical_compound
Nucleophile
Sulfinamide
Materials Chemistry
[CHIM]Chemical Sciences
Reactivity (chemistry)
Physical and Theoretical Chemistry
ComputingMilieux_MISCELLANEOUS
Amination
Palladium
Subjects
Details
- ISSN :
- 0022328X
- Volume :
- 760
- Database :
- OpenAIRE
- Journal :
- Journal of Organometallic Chemistry
- Accession number :
- edsair.doi.dedup.....f769ad76e9e0c7db2330fa648e6b9fbc