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Palladium‐Catalyzed Intramolecular Carbene Insertion into C(sp3)−H Bonds |
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| Authors: | Prof. Dr. Daniel Solé Francesco Mariani Prof. Dr. M.‐Lluïsa Bennasar Dr. Israel Fernández |
| Affiliation: | 1. Laboratori de Química Orgànica, Facultat de Farmàcia, Universitat de Barcelona, Barcelona, Spain;2. Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad Complutense de Madrid, Ciudad Universitaria, Madrid, Spain |
| Abstract: | A palladium‐catalyzed carbene insertion into C(sp3)?H bonds leading to pyrrolidines was developed. The coupling reaction can be catalyzed by both Pd0 and PdII, is regioselective, and shows a broad functional group tolerance. This reaction is the first example of palladium‐catalyzed C(sp3)?C(sp3) bond assembly starting from diazocarbonyl compounds. DFT calculations revealed that this direct C(sp3)?H bond functionalization reaction involves an unprecedented concerted metalation–deprotonation step. |
| Keywords: | carbene insertion density functional calculations diazo compounds palladium catalysis pyrrolidines |