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Synlett 2018; 29(09): 1181-1186
DOI: 10.1055/s-0036-1591982
DOI: 10.1055/s-0036-1591982
letter
Assessing the Activity of Lewis Bases Organocatalysts in Halonium-Induced Carbocyclization Reactions
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
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591982.
- Supporting Information
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For phosphine sulfide catalyzed halogenation reactions, see:
For a seminal contribution on phosphate-catalyzed enantioselective halolactonisation, see:
For a seminal contribution on phosphane-catalyzed enantioselective bromo-O-amidation, see:
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For a related enantioselective carbosulfenylation of alkenes in the presence of a chiral phosphorus selenide Lewis base catalyst, see: