Assessing the Activity of Lewis Bases Organocatalysts in Halonium-Induced Carbocyclization Reactions
- Resource Type
- Authors
- Véronique Michelet; Patrick Y. Toullec; Charlotte Grandclaudon; Mirko Ruamps; Raphaël Duboc
- Source
- Synlett. 29:1181-1186
- Subject
- 010405 organic chemistry
Organic Chemistry
Halogenation
010402 general chemistry
01 natural sciences
Medicinal chemistry
3. Good health
0104 chemical sciences
Catalysis
Reaction rate
chemistry.chemical_compound
chemistry
Organocatalysis
Selenide
Halonium ion
Lewis acids and bases
Derivative (chemistry)
- Language
- ISSN
- 1437-2096
0936-5214
Lewis bases were evaluated as catalysts for halocarbocyclization reactions of alkynylstyrenes and a cinnamylaniline derivative. Phosphines and phosphorus chalcogenides exhibited high activity for the conversion of alkynylstyrenes in the presence of N-halosuccinimides with up to a 30-fold increase of the initial reaction rate with respect to the background reaction. Phosphorus sulfides and selenides showed the best catalytic activity for the iodocarbocyclization of a cinnamylaniline derivative in the presence of diiodohydantoin. An asymmetric variant of the iodocarbocyclization reaction of an alkynylstyrene using a chiral phosphorus selenide resulted in a modest enantioselectivity.