N ‐Acyliminium Ion Chemistry: Highly Efficient and Versatile Carbon–Carbon Bond Formation by Nucleophilic Substitution of Hydroxy Groups Catalyzed by Sn(NTf 2 ) 4 | Zendy

Ben Othman Raja | Zendy; Affani Radouane | Zendy; Tranchant MarieJosé | Zendy; Antoniotti Sylvain | Zendy; Dalla Vincent | Zendy; Duñach Elisabet | Zendy

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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.

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