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Epoxides as Dual-Functionalized Alkylating Reagents in Catellani Reactions for the Assembly of Heterocycles
- Source :
- Synlett. 31:829-837
- Publication Year :
- 2020
- Publisher :
- Georg Thieme Verlag KG, 2020.
-
Abstract
- Reported is a cooperative catalytic system consisting of a complex of Pd with dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (XPhos) and the potassium salt of 5-norbornene-2-carboxylic acid that permits the use of epoxides as dual-functionalized alkylating reagents in Catellani-type reactions for the assembly of heterocycles. Salient features of this research include readily available substrates, use of the potassium salt of 5-norbornene-2-carboxylic acid as a catalytic mediator as well as a base, and excellent regioselectivity for the cleavage of epoxides. This mild, chemoselective, scalable, atom- and step-economic protocol offers a straightforward approach for the assembly of isochroman and 2,3-dihydrobenzofuran scaffolds.
- Subjects :
- chemistry.chemical_classification
010405 organic chemistry
Potassium
Organic Chemistry
chemistry.chemical_element
Salt (chemistry)
Regioselectivity
010402 general chemistry
01 natural sciences
Combinatorial chemistry
0104 chemical sciences
Catalysis
chemistry.chemical_compound
chemistry
XPhos
Reagent
Catellani reaction
Phosphine
Subjects
Details
- ISSN :
- 14372096 and 09365214
- Volume :
- 31
- Database :
- OpenAIRE
- Journal :
- Synlett
- Accession number :
- edsair.doi...........a7b04466116c73a8a872c943c854c4cd