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1 article(s) from Piller, Fabian M

Functionalization of heterocyclic compounds using polyfunctional magnesium and zinc reagents

Paul Knochel,
Matthias A. Schade,
Sebastian Bernhardt,
Georg Manolikakes,
Albrecht Metzger,
Fabian M. Piller,
Christoph J. Rohbogner and
Marc Mosrin

Beilstein J. Org. Chem. 2011, 7, 1261–1277, doi:10.3762/bjoc.7.147

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Graphical Abstract

Scheme 1: Preparation of polyfunctional heteroarylzinc reagents.

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Scheme 2: LiCl-mediated insertion of zinc dust to aryl and heteroaryl iodides.

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Scheme 3: Selective insertions of Zn in the presence of LiCl.

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Scheme 4: Chemoselective insertion of zinc in the presence of LiCl.

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Scheme 5: Preparation and reactions of benzylic zinc reagents.

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Scheme 6: Ni-catalyzed cross-coupling of benzylic zinc reagent 34 with ethyl 2-chloronicotinate.

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Scheme 7: In situ generation of arylzinc reagents using Mg in the presence of LiCl and ZnCl₂.

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Scheme 8: Zincation of heterocycles with TMP₂Zn (42).

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Scheme 9: Preparation of highly functionalized zincated heterocycles using TMP₂Zn·2MgCl₂·2LiCl (42).

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Scheme 10: Microwave-accelerated zincation of heterocycles using TMP₂Zn·2MgCl₂·2LiCl (42).

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Scheme 11: The I/Mg-exchange as a metal-metathesis reaction.

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Scheme 12: Regioselective Br/Mg-exchange of dibromoquinolines 65 and 68.

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Scheme 13: Improved reagents for the regioselective Br/Mg-exchange on bromoquinolines.

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Scheme 14: Synthesis of ellipticine (83) using an I/Mg-exchange reaction.

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Scheme 15: An oxidative amination leading to the biologically active adenine, purvalanol A (84).

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Scheme 16: Preparation of polyfunctional arylmagnesium reagents using Mg in the presence of LiCl.

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Scheme 17: Preparation of polyfunctional magnesium reagents starting from organic chlorides.

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Scheme 18: Selective multiple magnesiation of the pyrimidine ring.

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Scheme 19: Synthesis of a p38 kinase inhibitor 119 and of a sPLA2 inhibitor 123.

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Scheme 20: Synthesis of highly substituted indoles of type 128.

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Scheme 21: Efficient magnesiations of polyfunctional aromatics and heterocycles using TMP₂Mg·2LiCl (129).

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Scheme 22: Negishi cross-coupling in the presence of substrates bearing an NH- or an OH-group.

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Scheme 23: Negishi cross-coupling in the presence of a serine moiety.

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Scheme 24: Radical catalysis for the performance of very fast Kumada reactions.

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Scheme 25: MgCl₂-mediated addition of functionalized aromatic, heteroaromatic, alkyl and benzylic organozincs ...

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Published 13 Sep 2011

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