Investigation of the catalytic activity of poly(4-vinylpyridine) supported iodine as a new, efficient and recoverable catalyst for regioselective ring opening of epoxides

被引:28
作者
Khalig, Nader Ghaffari [1 ]
机构
[1] Univ Guilan, Dept Chem, Rasht, Iran
关键词
LEWIS-ACID CATALYST; ORGANIC-SYNTHESIS; MOLECULAR-IODINE; HIGHLY EFFICIENT; ACETIC-ACID; CHLOROFORM SOLUTION; ALCOHOLS; PYRIDINE; MILD; CHLORIDE;
D O I
10.1039/c2ra20080e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient methodology for ring opening of epoxides in alcohols, water and acetic acid promoted by poly(4-vinylpyridine) supported iodine under neutral conditions, has been demonstrated. The reactions occur with high regioselectivity. The products were obtained in good to excellent yields. The reaction of optically active styrene oxide with P(4-VPI)I-+(3)- in methanol was found to be very stereospecific and the product was isolated in 88% ee. This catalyst is stable and can be easily regenerated and used.
引用
收藏
页码:3321 / 3327
页数:7
相关论文
共 59 条
[1]   APPLICATION OF FUNCTIONALIZED POLYMERS IN ORGANIC-SYNTHESIS [J].
AKELAH, A ;
SHERRINGTON, DC .
CHEMICAL REVIEWS, 1981, 81 (06) :557-587
[2]  
[Anonymous], SYNTHESIS SEPARATION
[3]   Anomalous electrolytes I The electrical conductivity of solutions of iodine and cyanogen iodide in pyridine [J].
Audrieth, LF ;
Birr, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1933, 55 :668-673
[4]  
Banerjee AK, 2006, J SCI IND RES INDIA, V65, P299
[5]   Copper(II) tetrafluoroborate catalyzed ring-opening reaction of epoxides with alcohols at room temperature [J].
Barluenga, J ;
Vázquez-Villa, H ;
Ballesteros, A ;
González, JM .
ORGANIC LETTERS, 2002, 4 (17) :2817-2819
[6]  
Biswas A, 2009, CHIM OGGI, V27, P33
[7]  
CHEUDARY BM, 1996, SYNTHETIC COMMUN, V26, P2989
[8]   Molecular Iodine in Protection and Deprotection Chemistry [J].
Das, Subrato ;
Borah, Ruli ;
Devi, Rashmi Rekha ;
Thakur, Ashim Jyoti .
SYNLETT, 2008, (18) :2741-2762
[9]   Rhodium-catalyzed ring opening of vinyl epoxides with alcohols and aromatic amines [J].
Fagnou, K ;
Lautens, M .
ORGANIC LETTERS, 2000, 2 (15) :2319-2321
[10]   Aluminumdodecatungstophosphate (AlPW12O40) as a reusable Lewis acid catalyst -: Facile regioselective ring opening of epoxides with alcohols, acetic acid and thiols [J].
Firouzabadi, H ;
Iranpoor, N ;
Jafari, AA ;
Makarem, S .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 250 (1-2) :237-242