Convenient and Practical Alkynylation of Heteronucleophiles with Copper Acetylides

Autor:	Estelle Loire, Kévin Jouvin, Gwilherm Evano, Céline Guissart, Jérémy Heimburger, Anouar Laouiti, Cédric Theunissen, Morgan Lecomte
Rok vydání:	2014
Předmět:	chemistry.chemical_classification Chemistry Organic Chemistry Alkyne chemistry.chemical_element Combinatorial chemistry Copper Catalysis Umpolung chemistry.chemical_compound Nucleophile Alkynylation Reagent Imidazole Reactivity (chemistry)
Zdroj:	Synthesis. 46:1157-1166
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-0033-1341025
Popis:	Copper acetylides, readily available reagents which are characterized by their lack of reactivity, can be simply activated by oxidation with oxygen in the presence of simple nitrogen ligands such as TMEDA or imidazole derivatives. Upon activation, these nucleophilic species undergo a formal umpolung and can transfer their alkyne subunit to a wide range of heteronucleophiles, including amides, oxazolidinones, imines, and dialkyl phosphites. This alkynylation, which provides one of the most practical entry to useful building blocks such as ynamides, ynimines, and alkynylphosphonates, proceeds under especially mild conditions and can be easily performed on a multigram scale.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::e3dc53dc49cb9404b193794e539de726 https://doi.org/10.1055/s-0033-1341025 Zobrazit plný text záznamu