A General Catalytic Hydroamidation of 1,3-Dienes: Atom-Efficient Synthesis of N-Allyl Heterocycles, Amides, and Sulfonamides†
Correction(s) for this article
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Berichtigung: A General Catalytic Hydroamidation of 1,3-Dienes: Atom-Efficient Synthesis of N-Allyl Heterocycles, Amides, and Sulfonamides
- Volume 129Issue 52Angewandte Chemie
- pages: 16656-16658
- First Published online: December 19, 2017
Dr. Debasis Banerjee
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock (Germany) http://www.catalysis.de
Search for more papers by this authorDr. Kathrin Junge
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock (Germany) http://www.catalysis.de
Search for more papers by this authorCorresponding Author
Prof. Dr. Matthias Beller
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock (Germany) http://www.catalysis.de
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock (Germany) http://www.catalysis.deSearch for more papers by this authorDr. Debasis Banerjee
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock (Germany) http://www.catalysis.de
Search for more papers by this authorDr. Kathrin Junge
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock (Germany) http://www.catalysis.de
Search for more papers by this authorCorresponding Author
Prof. Dr. Matthias Beller
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock (Germany) http://www.catalysis.de
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock (Germany) http://www.catalysis.deSearch for more papers by this authorThis research was funded by the State of Mecklenburg–Western Pomerania, the BMBF, and the DFG (Leibniz Prize). We thank Dr. W. Baumann, Dr. C. Fischer, S. Buchholz, S. Schareina, A. Koch, and S. Rossmeisl (all at LIKAT) for their excellent technical and analytical support.
Abstract
Transition-metal-catalyzed hydroamination reactions are sustainable and atom-economical CN bond-forming processes. Although remarkable progress has been made in the inter- and intramolecular amination of olefins and 1,3-dienes, related intermolecular reactions of amides are still much less known. Control of the regioselectivity without analogous telomerization is the particular challenge in the catalytic hydroamidation of alkenes and 1,3-dienes. Herein, we report a general protocol for the hydroamidation of electron-deficient N-heterocyclic amides and sulfonamides with 1,3-dienes and vinyl pyridines in the presence of a catalyst derived from [{Pd(π-cinnamyl)Cl}2] and ligand L7 or L10. The reactions proceeded in good to excellent yield with high regioselectivity. The practical utility of our method is demonstrated by the hydroamidation of functionalized biologically active substrates. The high regioselectivity for linear amide products makes the procedure useful for the synthesis of a variety of allylic amides.
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