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Dual-role of PtCl2 Catalysis in the Intramolecular Cyclization of (Hetero)Aryl-Allenes for the Facile Construction of Substituted 2,3-Dihydropyrroles and Polyheterocyclic Skeletons

Abstract

A Pt(II)-catalyzed cyclization of (hetero)aryl-allenes has been developed, providing controllable synthesis of substituted 2,3-dihydropyrroles and polyheterocyclic skeletons. Temperature plays an important role to determine the product distribution: the reaction gives 2,3-dihydropyrroles when running at 70 oC, while further Friedel-Crafts type annulation takes place when the reaction temperature increased to 90 oC. Another notable feature of this method is the dual-role of Pt(II) catalyst, initiating the migration of (hetero)arylmethylene group and the subsequent Friedel-Crafts type annulation, respectively. The substrate scope is broad and a variety of functional groups are tolerated. Moreover, the synthetic utilization is further demonstrated by gram scale synthesis and simple transformation of the polyheterocyclic product into other drug-candidate molecules.

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Publication details

The article was received on 04 Mar 2017, accepted on 30 Mar 2017 and first published on 06 Apr 2017


Article type: Communication
DOI: 10.1039/C7CC01684K
Citation: Chem. Commun., 2017, Accepted Manuscript
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    Dual-role of PtCl2 Catalysis in the Intramolecular Cyclization of (Hetero)Aryl-Allenes for the Facile Construction of Substituted 2,3-Dihydropyrroles and Polyheterocyclic Skeletons

    Y. Zhang, Y. Wei, X. Tang and M. Shi, Chem. Commun., 2017, Accepted Manuscript , DOI: 10.1039/C7CC01684K

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