Click-alkynylation of N- and P-nucleophiles by oxidative cross-coupling with alkynylcopper reagents: a general synthesis of ynamides and alkynylphosphonates

Autor:	Gwilherm Evano, Jérémy Heimburger, Kévin Jouvin
Rok vydání:	2012
Předmět:	chemistry.chemical_classification Alkyne chemistry.chemical_element General Chemistry Oxidative phosphorylation Polymer Combinatorial chemistry Copper Umpolung Coupling (electronics) chemistry Nucleophile Reagent Organic chemistry
Zdroj:	Chem. Sci.. 3:756-760
ISSN:	2041-6539 2041-6520
DOI:	10.1039/c2sc00842d
Popis:	Nitrogen- and phosphorus-based nucleophiles can be smoothly transformed to the corresponding heteroatom-substituted alkynes by simple reaction at room temperature and under an oxygen atmosphere with copper acetylides. These stable, readily available, polymers act as especially efficient reagents for the introduction of an alkyne group under remarkably mild oxidative conditions which allow for their formal umpolung. Chelating ligands such as TMEDA and N-methylimidazole are efficient organic promoters, allowing for clean and fast oxidative cross-couplings, even with complex substrates.
Databáze:	OpenAIRE
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