title: Synthesis of five- and six-membered dihalogenated heterocyclic compounds by electrophile-triggered cyclization.
abstract: Highly substituted dihalogenated dihydrofurans, dihydropyrroles, and dihydro-2H-pyrans bearing alkyl, vinyl, aryl, and heteroaryl moieties can be prepared in good to excellent yields (up to 99%) by allowing 1,4-butyne-diol, 4-aminobut-2-yn-1-ol, and pent-2-yne-1,5-diol derivatives to react with different electrophiles (I(2), IBr, and ICl) at room temperature. Both halogen atoms generated from electrophiles were used effectively. The resulting halides can be further exploited by using palladium-catalyzed coupling reactions. The presence of trace amount of water is essential for this electrophilic cyclization.
authors: State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China.
authors: Ke-Gong
authors: KG
authors: Ji
authors: Hai-Tao
authors: HT
authors: Zhu
authors: Fang
authors: F
authors: Yang
authors: Ali
authors: A
authors: Shaukat
authors: Xiao-Feng
authors: XF
authors: Xia
authors: Yan-Fang
authors: YF
authors: Yang
authors: Xue-Yuan
authors: XY
authors: Liu
authors: Yong-Min
authors: YM
authors: Liang
mesh_terms: D018360:Crystallography, X-Ray; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D005663:Furans; D006571:Heterocyclic Compounds; D011714:Pyrans; D011758:Pyrroles