Vinyl Triflimides—A Case of Assisted Vinyl Cation Formation

Autor:	Meike Niggemann, Sebastian Schroeder, Niklas Gaelings, Christina Strauch
Rok vydání:	2019
Předmět:	chemistry.chemical_classification 010405 organic chemistry Chemistry Supramolecular chemistry Alkyne Protonation General Chemistry 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences Nucleophile Polymer chemistry Stereoselectivity Selectivity Vinyl cation
Zdroj:	Angewandte Chemie International Edition. 58:5119-5123
ISSN:	1521-3773 1433-7851
DOI:	10.1002/anie.201810916
Popis:	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 (Li2 NTf2+ ⋅3 H2 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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::24d3f4b2c9c18e11061583e998bb855b https://doi.org/10.1002/anie.201810916 Zobrazit plný text záznamu Plný text