Synthesis of five- and six-membered dihalogenated heterocyclic compounds by electrophile-triggered cyclization.
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.
Ji
Ke-Gong
KG
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China.
Zhu
Hai-Tao
HT
Yang
Fang
F
Shaukat
Ali
A
Xia
Xiao-Feng
XF
Yang
Yan-Fang
YF
Liu
Xue-Yuan
XY
Liang
Yong-Min
YM
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
D005663:Furans; D006571:Heterocyclic Compounds; D011714:Pyrans; D011758:Pyrroles