trans ‐Carbocarbonation of Internal Alkynes through a Formal anti ‐Carbopalladation/C−H Activation Cascade

Autor:	Andreas Reding, Peter G. Jones, Daniel B. Werz
Rok vydání:	2018
Předmět:	chemistry.chemical_classification Silylation Double bond Stereochemistry 010405 organic chemistry Alkyne General Chemistry General Medicine Triple bond Ring (chemistry) 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences Cascade reaction chemistry Catalytic cycle Intramolecular force
Zdroj:	Angewandte Chemie. 130:10770-10774
ISSN:	1521-3757 0044-8249
Popis:	An intramolecular Pd-catalyzed cascade reaction is presented that consists of a formal anti-carbopalladation of a C-C triple bond followed by C-H activation. As a result, oligocyclic ring systems with an embedded tetrasubstituted double bond are formed. The key to success in affording the trans geometry of the emerging double bond are alkyne units with residues that must not undergo β-hydride elimination (e.g., t-butyl or silyl groups). Silyl groups proved to be a perfect handle to further convert the tetrasubstituted alkenes. The evaluation of kinetic data with a deuterium-labeled compound and X-ray analyses of trapped intermediates provided additional insight into the catalytic cycle.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::15aab600a9c7c69151ff59e73e85a03a https://doi.org/10.1002/ange.201805399 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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