1256498-53-9Relevant academic research and scientific papers
Assessing the Activity of Lewis Bases Organocatalysts in Halonium-Induced Carbocyclization Reactions
Grandclaudon, Charlotte,Ruamps, Mirko,Duboc, Rapha?l,Michelet, Véronique,Toullec, Patrick Y.
, p. 1181 - 1186 (2018)
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.
Synthesis of Functionalized 1H-Indenes and Benzofulvenes through Iodocyclization of o-(Alkynyl)styrenes
García-García, Patricia,Sanjuán, Ana M.,Rashid, Muhammad A.,Martínez-Cuezva, Alberto,Fernández-Rodríguez, Manuel A.,Rodríguez, Félix,Sanz, Roberto
, p. 1155 - 1165 (2018/06/18)
A convenient method for the preparation of synthetically useful 3-iodoindene derivatives has been developed. This protocol, based on the 5-endo iodocyclization reaction of o-(alkynyl)styrenes, represents one of the scarce examples of halocyclizations using olefins as nucleophilic counterparts and allows the synthesis of both 3-iodo-1H-indenes (from β-alkyl-β-alkyl/aryl-o-(alkynyl)styrenes) and 3-iodobenzofulvenes (from β,β-diaryl-o-(alkynyl)styrenes) in good yields under mild reaction conditions. In addition, related alkoxyiodocyclization processes are described, which are particularly interesting in their intramolecular version because they allow the synthesis of heteropolycyclic structures containing the indene core. Finally, the usefulness of the prepared 3-iodoindenes has been demonstrated by the synthesis of several polysubstituted indene derivatives through conventional palladium-catalyzed cross-coupling reactions and iodine-lithium exchange processes.
Halocyclization of o-(alkynyl)styrenes. Synthesis of 3-halo-1H-indenes
Sanz, Roberto,Martinez, Alberto,Garcia-Garcia, Patricia,Fernandez-Rodriguez, Manuel A.,Rashid, Muhammad A.,Rodriguez, Felix
supporting information; experimental part, p. 7427 - 7429 (2010/11/18)
o-(Alkynyl)styrenes undergo halocarbocyclization processes via a 5-endo-dig ring closure. By this strategy an efficient synthesis of 3-halo-1H-indene derivatives has been developed.
