Affiliation:
1. Univ Rennes CNRS ISCR (Institut des Sciences Chimiques de Rennes) UMR 6226 F-35000 Rennes France
2. Laboratoire de Synthèse Organique Appliquée Faculté des Sciences Exactes et Appliquées Université Oran 1 Ahmed Ben Bella BP 1524 El M'Naouer 31000 Oran Algeria
Abstract
AbstractWhen 2‐iodobenzofuran was treated sequentially with lithium 2,2,6,6‐tetramethylpiperidide in tetrahydrofuran at −50 °C and an aldehyde, the 2‐substituted 3‐iodobenzofuran resulting from the halogen dance was the only isolated product. However, from 2‐iodobenzothiophene, these conditions led to mixtures in which the 2‐substituted 3‐iodobenzothiophene was always accompanied by the 2‐substituted benzothiophene. The use of 2‐bromobenzothiophene as a catalyst made it possible to significantly reduce this competitive dehalogenation. To confirm the halogen dance reaction, the products were unambiguously synthesized by using direct halogenations and deprotolithiation‐trapping sequences as key steps. Our efforts to access 2,7‐disubstituted and 7‐substituted derivatives of benzofuran and benzothiophene have also been reported.
Funder
Centre National de la Recherche Scientifique
Subject
Organic Chemistry,Physical and Theoretical Chemistry
Cited by
2 articles.
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