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N ‐Acyliminium Ion Chemistry: Highly Efficient and Versatile Carbon–Carbon Bond Formation by Nucleophilic Substitution of Hydroxy Groups Catalyzed by Sn(NTf 2 ) 4
Author(s) -
Ben Othman Raja,
Affani Radouane,
Tranchant MarieJosé,
Antoniotti Sylvain,
Dalla Vincent,
Duñach Elisabet
Publication year - 2010
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.200906036
Subject(s) - catalysis , nucleophile , reagent , chemistry , methylene , carbon fibers , nucleophilic substitution , atom (system on chip) , combinatorial chemistry , ion , medicinal chemistry , organic chemistry , computer science , parallel computing , algorithm , composite number
Atom‐economical : Unmodified hemi‐N,O‐acetals are used in a catalytic, highly efficient α‐amidoalkylation of a broad range of carbon‐centered nucleophiles, including silicon‐based components, active methylene derivatives, electron‐rich arenes, and even simple ketones (see scheme). The reactions proceed in a highly efficient manner and typically require only 1 mol % of the Lewis superacidic reagent Sn(NTf 2 ) 4 as the catalyst.