title: Transition-metal-free synthesis of N-(1-alkenyl)imidazoles by potassium phosphate-promoted addition reaction of alkynes to imidazoles.
abstract: The addition reaction of alkynes to N-heterocycles by simply heating in DMSO with potassium phosphate is reported. Good yields with high stereoselectivity could be achieved for a range of substrates. The scope is quite general for both amines and phenylacetylenes. In addition, internal alkynes and α-bromostyrene were also examined in this reaction. This process is efficient and useful for the synthesis of (Z)-N-(1-alkenyl)imidazoles and related Z products. Thus, the reaction is useful because of the importance of the imidazole scaffold.
authors.affiliation: Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123 (P. R. China), Fax: (+86) 512-65880403.
authors.forename: Linhua
authors.initials: L
authors.lastname: Lu
authors.forename: Hong
authors.initials: H
authors.lastname: Yan
authors.forename: Defu
authors.initials: D
authors.lastname: Liu
authors.forename: Guangwei
authors.initials: G
authors.lastname: Rong
authors.forename: Jincheng
authors.initials: J
authors.lastname: Mao
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010710:Phosphates / Q000737:chemistry*; D017680:Potassium Compounds / Q000737:chemistry*
chemical_list: D000480:Alkynes; D007093:Imidazoles; D010710:Phosphates; D017680:Potassium Compounds; C013216:potassium phosphate
keywords: alkynes; imidazoles; nitrogen heterocycles; nucleophilic addition; synthetic methods