Trifluoroacetic acid catalyzed tetrahydropyranylation of alcohols and phenols and direct conversion of THP ethers into acetates

被引：0
|
作者：
Bodipati, Naganjaneyulu [1 ]
Palla, Srinivasa Rao [1 ]
Peddinti, Rama Krishna [1 ]
机构：
[1] Indian Inst Technol, Dept Chem, Roorkee 247667, Uttar Pradesh, India
来源：
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY | 2012年 / 51卷 / 02期
关键词：
Tetrahydropyranylation; trifluoroacetic acid; alcohols; phenols; THP ethers; acetates; SOLVENT-FREE TETRAHYDROPYRANYLATION; ONE-STEP CONVERSION; EFFICIENT CATALYST; HIGHLY EFFICIENT; CHEMOSELECTIVE TETRAHYDROPYRANYLATION; SYNTHETIC PROTOCOL; MILD; DEPROTECTION; TRIFLATE; CHLORIDE;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple procedure for tetrahydropyranylation of alcohols and phenols in dichloromethane and their depyranylation in methanol in the presence of trifluoroacetic acid at ambient temperature is described. This methodology is useful for substrates having functionalities such as ester, amide, nitro, aldehyde and olefinic bonds. Trifluoroacetic acid mediated direct conversion of tetrahydropyranyl ethers into their corresponding acetates is also described.
引用
收藏
页码：356 / 361
页数：6
相关论文
共 50 条
  • [1] Mild and efficient tetrahydropyranylation of alcohols and dehydropyranylation of THP ethers catalyzed by ferric perchlorate
    Heravi, MM
    Behbahani, FK
    Oskooie, HA
    Shoar, RH
    TETRAHEDRON LETTERS, 2005, 46 (15) : 2543 - 2545
  • [2] Copper nitrate/acetic acid as an efficient synergistic catalytic system for the chemoselective tetrahydropyranylation of alcohols and phenols
    Wang, Min
    Song, Zhi-Guo
    Gong, Hong
    Jiang, Heng
    MONATSHEFTE FUR CHEMIE, 2009, 140 (02): : 177 - 179
  • [3] Tetrahydropyranylation of alcohols and phenols catalyzed by a new polystyrene-bound tin(IV) porphyrin
    Moghadam, Majid
    Tangestaninejad, Shahram
    Mirkhani, Valiollah
    Mohammadpoor-Baltork, Iraj
    Gharaati, Shadab
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2011, 337 (1-2) : 95 - 101
  • [4] Niobium(V) chloride: an active Lewis acid catalyst for tetrahydropyranylation of alcohols and phenols
    Nagaiah, K
    Reddy, BVS
    Sreenu, D
    Narsaiah, AV
    ARKIVOC, 2005, : 192 - 199
  • [5] Highly efficient tetrahydropyranylation of alcohols and phenols catalyzed by a new and reusable high-valent vanadium(IV) porphyrin
    Taghavi, S. Abdolmanaf
    Moghadam, Majid
    Mohammadpoor-Baltork, Iraj
    Tangestaninejad, Shahram
    Mirkhani, Valiollah
    Khosropour, Ahmad Reza
    COMPTES RENDUS CHIMIE, 2011, 14 (12) : 1095 - 1102
  • [6] Zeolite-catalyzed environmentally friendly tetrahydropyranylation of alcohols and phenols
    Hegedüs, A
    Vígh, I
    Hell, Z
    SYNTHETIC COMMUNICATIONS, 2004, 34 (22) : 4145 - 4152
  • [7] Efficient tetrahydropyranylation of phenols and alcohols catalyzed by supported Mo and W keggin heteropolyacids
    Romanelli, GP
    Vázquez, PG
    Pizzio, LR
    Cáceres, CV
    Blanco, MN
    Autino, JC
    SYNTHETIC COMMUNICATIONS, 2003, 33 (08) : 1359 - 1365
  • [8] Microwave accelerated tetrahydropyranylation and detetrahydropyranylation of alcohols, phenols, and thiols catalyzed by hydrated zirconia
    Gajare, AS
    Sabde, DP
    Shingare, MS
    Wakharkar, RD
    SYNTHETIC COMMUNICATIONS, 2002, 32 (10) : 1549 - 1555
  • [9] Iron-catalyzed solvent-free conversion of alcohols and phenols into diphenylmethyl (DPM) ethers
    Namboodiri, VV
    Varma, RS
    TETRAHEDRON LETTERS, 2002, 43 (26) : 4593 - 4595
  • [10] Polystyrene-supported GaCl3: A new, highly efficient and recyclable heterogeneous Lewis acid catalyst for tetrahydropyranylation of alcohols and phenols
    Rahmatpour, Ali
    POLYHEDRON, 2012, 44 (01) : 66 - 71
12345