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Palladium‐Catalyzed Intramolecular Carbene Insertion into C(sp 3 )−H Bonds
Author(s) -
Solé Daniel,
Mariani Francesco,
Bennasar M.Lluïsa,
Fernández Israel
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201602020
Subject(s) - carbene , palladium , metalation , intramolecular force , chemistry , regioselectivity , catalysis , deprotonation , medicinal chemistry , insertion reaction , transmetalation , coupling reaction , functional group , stereochemistry , photochemistry , organic chemistry , polymer , ion
A palladium‐catalyzed carbene insertion into C(sp 3 )−H bonds leading to pyrrolidines was developed. The coupling reaction can be catalyzed by both Pd 0 and Pd II , is regioselective, and shows a broad functional group tolerance. This reaction is the first example of palladium‐catalyzed C(sp 3 )−C(sp 3 ) bond assembly starting from diazocarbonyl compounds. DFT calculations revealed that this direct C(sp 3 )−H bond functionalization reaction involves an unprecedented concerted metalation–deprotonation step.