Highly efficient protection of alcohols and phenols catalysed by tin porphyrin supported on MIL-101

被引:12
作者
Zadehahmadi, Farnaz [1 ]
Tangestaninejad, Shahram [1 ]
Moghadam, Majid [1 ]
Mirkhani, Valiollah [1 ]
Mohammadpoor-Baltork, Iraj [1 ]
Kardanpour, Reihaneh [1 ]
机构
[1] Univ Isfahan, Catalysis Div, Dept Chem, Esfahan 8174673441, Iran
关键词
metal-organic framework; tin(IV) porphyrin; MIL-101(Cr); trimethylsilylation; tetrahydropyranylation; METAL-ORGANIC FRAMEWORK; HEXAMETHYLDISILAZANE HMDS; RECYCLABLE CATALYST; CHEMOSELECTIVE TRIMETHYLSILYLATION; TIN(IV) PORPHYRIN; FUNCTIONAL-GROUPS; SILYL ETHERS; TETRAHYDROPYRANYLATION; MILD; DEPROTECTION;
D O I
10.1002/aoc.3270
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The catalytic activity of 5,10,15,20-tetrakis(4-aminophenyl)porphyrinatotin(IV) trifluoromethanesulfonate, [Sn-IV(TNH2PP)(OTf)(2)], supported on chloromethylated MIL-101, was investigated in the trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) and also their tetrahydropyranylation with 3,4-dihydro-2H-pyran. Excellent yields, mild reaction conditions, short reaction times and reusability of the catalyst without significant decrease in its initial activity are noteworthy advantages of this supported catalyst. Copyright (c) 2015 John Wiley & Sons, Ltd.
引用
收藏
页码:209 / 215
页数:7
相关论文
共 58 条
[1]   ON PREPARATION OF METALLOPORPHYRINS [J].
ADLER, AD ;
LONGO, FR ;
KAMPAS, F ;
KIM, J .
JOURNAL OF INORGANIC & NUCLEAR CHEMISTRY, 1970, 32 (07) :2443-&
[2]   Zeolite-like metal-organic frameworks as platforms for applications:: On metalloporphyrin-based catalysts [J].
Alkordi, Mohamed H. ;
Liu, Yunling ;
Larsen, Randy W. ;
Eubank, Jarrod F. ;
Eddaoudi, Mohamed .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (38) :12639-+
[3]   ELECTROCHEMICAL POLYMERIZATION OF AMINO-SUBSTITUTED, PYRROLE-SUBSTITUTED, AND HYDROXY-SUBSTITUTED TETRAPHENYLPORPHYRINS [J].
BETTELHEIM, A ;
WHITE, BA ;
RAYBUCK, SA ;
MURRAY, RW .
INORGANIC CHEMISTRY, 1987, 26 (07) :1009-1017
[4]   {[K.18-Crown-6]Br3}n: A tribromide catalyst for the catalytic protection of amines and alcohols [J].
Chehardoli, Gholamabbas ;
Zolfigol, Mohammad Ali ;
Derakhshanpanah, Fateme .
CHINESE JOURNAL OF CATALYSIS, 2013, 34 (09) :1730-1733
[5]   Vanadyl(IV) acetate: a mild and efficient heterogeneous catalyst for the tetrahydropyranylation of alcohols, thiols and phenols [J].
Choudary, BM ;
Neeraja, V ;
Kantam, ML .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2001, 175 (1-2) :169-172
[6]   Heterogeneous catalysis in trimethylsilylation of alcohols and phenols by zirconium sulfophenyl phosphonate [J].
Curini, M ;
Epifano, F ;
Marcotullio, MC ;
Rosati, O ;
Costantino, U .
SYNTHETIC COMMUNICATIONS, 1999, 29 (03) :541-546
[7]   Synthesis of sulfonic acid functionalized carbon catalyst from glycerol pitch and its application for tetrahydropyranyl protection/deprotection of alcohols and phenols [J].
Devi, B. L. A. Prabhavathi ;
Gangadhar, K. N. ;
Kumar, K. L. N. Siva ;
Shanker, K. Shiva ;
Prasad, R. B. N. ;
Prasad, P. S. Sai .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2011, 345 (1-2) :96-100
[8]   Hybrid porous solids:: past, present, future [J].
Ferey, Gerard .
CHEMICAL SOCIETY REVIEWS, 2008, 37 (01) :191-214
[9]   Tungstophosphoric acid (H3PW12O40) as a heterogeneous inorganic catalyst.: Activation of hexamethyldisilazane (HMDS) by tungstophosphoric acid for efficient and selective solvent-free O-silylation reactions [J].
Firouzabadi, H ;
Iranpoor, N ;
Amani, K ;
Nowrouzi, F .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (23) :2601-2604
[10]   Highly regio- and chemoselective silylation of diethyl α-hydroxyphosphonates, alcohols and phenols in the presence of solid TiCl3(OTf) as a catalyst with hexamethyldisilazane (HMDS) at room temperature in the absence of solvent [J].
Firouzabadi, Habib ;
Iranpoor, Nasser ;
Farahi, Soghra .
CATALYSIS COMMUNICATIONS, 2009, 10 (11) :1547-1550