Vinyl Triflimides—A Case of Assisted Vinyl Cation Formation | Zendy

Schroeder Sebastian | Zendy; Strauch Christina | Zendy; Gaelings Niklas | Zendy; Niggemann Meike | Zendy

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Vinyl Triflimides—A Case of Assisted Vinyl Cation Formation

Author(s) -

Schroeder Sebastian,

Strauch Christina,

Gaelings Niklas,

Niggemann Meike

Publication year - 2019

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.201810916

Subject(s) - carbocation , nucleophile , protonation , chemistry , alkyne , stereoselectivity , selectivity , supramolecular chemistry , combinatorial chemistry , organic chemistry , molecule , ion , catalysis

A new concept for selectivity control in carbocation‐driven reactions has been identified which allows for the chemo‐, regio‐, and stereoselective addition of nucleophiles to alkynes—assisted vinyl cation formation—enabled by a Li + ‐based supramolecular framework. Mechanistic analysis of a model complex (Li 2 NTf 2 + ⋅3 H 2 O) confirms that solely the formation of a complex between the incoming nucleophile and the transition state of the alkyne protonation is responsible for the resulting selective N addition to the vinyl cation. Into the bargain, a general, operationally simple synthetic procedure to previously inaccessible vinyl triflimides is provided.

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