Synlett 2018; 29(09): 1181-1186
DOI: 10.1055/s-0036-1591982
letter
© Georg Thieme Verlag Stuttgart · New York

Assessing the Activity of Lewis Bases Organocatalysts in Halonium-Induced Carbocyclization Reactions

Charlotte Grandclaudon
a  Institut de Recherche de Chimie Paris PSL Research University, Chimie ParisTech-CNRS, 11 Rue P. et M. Curie, 75005 Paris, France
,
Mirko Ruamps
a  Institut de Recherche de Chimie Paris PSL Research University, Chimie ParisTech-CNRS, 11 Rue P. et M. Curie, 75005 Paris, France
,
Raphaël Duboc
a  Institut de Recherche de Chimie Paris PSL Research University, Chimie ParisTech-CNRS, 11 Rue P. et M. Curie, 75005 Paris, France
,
a  Institut de Recherche de Chimie Paris PSL Research University, Chimie ParisTech-CNRS, 11 Rue P. et M. Curie, 75005 Paris, France
b  Institut de Chimie de Nice, Université Nice Sophia Antipolis UMR CNRS, 7272 Parc Valrose, 06108 Nice, France
,
a  Institut de Recherche de Chimie Paris PSL Research University, Chimie ParisTech-CNRS, 11 Rue P. et M. Curie, 75005 Paris, France
c  Institute of Molecular Sciences University of Bordeaux, 351, Cours de la Libération, 33405 Talence, France   Email: [email protected]
› Author Affiliations
This work was supported by a grant (ANR-13-JS07-0010) from the Agence Nationale de la Recherche. This work was also supported by the Ministère de l’Education et de la Recherche and the Centre National de la Recherche Scientifique (CNRS).

Further Information

Publication History

Received: 21 February 2018

Accepted after revision: 14 March 2018

Publication Date:
09 April 2018 (online)


Abstract

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.

Supporting Information

 
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