Synthesis of γ-halogenated ketones via the Ce(IV)-mediated oxidative coupling of cyclobutanols and inorganic halides

被引:42
作者
Casey, Brian M. [1 ]
Eakin, Cynthia A. [1 ]
Flowers, Robert A., II [1 ]
机构
[1] Lehigh Univ, Dept Chem, Bethlehem, PA 18015 USA
基金
美国国家卫生研究院;
关键词
CAN; Cyclobutanol; gamma-Substituted ketone; Oxidative coupling; CERIUM(IV) AMMONIUM-NITRATE; SOLVENT-DEPENDENT CHEMOSELECTIVITIES; RADICAL-CATION; ALKYL-HALIDES; EFFICIENT;
D O I
10.1016/j.tetlet.2008.12.114
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A straightforward method for the synthesis of gamma-halo-substituted ketones formed via the CAN-initiated oxidative addition of halides to 1-substituted cyclobutanols has been developed. This method has short reaction times, and provides access to a range of bromo and iodo gamma-substituted ketones in good to excellent yields. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1264 / 1266
页数:3
相关论文
共 22 条
  • [11] Recent advances in synthetic transformations mediated by cerium(IV) ammonium nitrate
    Nair, V
    Balagopal, L
    Rajan, R
    Mathew, J
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (01) : 21 - 30
  • [12] Carbon-heteroatom bond-forming reactions mediated by cerium(IV) ammonium nitrate: An overview
    Nair, V
    Panicker, SB
    Nair, LG
    George, TG
    Augustine, A
    [J]. SYNLETT, 2003, (02) : 156 - 165
  • [13] An efficient bromination of alkenes using cerium(IV) ammonium nitrate (CAN) and potassium bromide
    Nair, V
    Panicker, SB
    Augustine, A
    George, TG
    Thomas, S
    Vairamani, M
    [J]. TETRAHEDRON, 2001, 57 (34) : 7417 - 7422
  • [14] Cerium(IV) ammonium nitrate mediated addition of thiocyanate and azide to styrenes: Expeditious routes to phenacyl thiocyanates and phenacyl azides
    Nair, V
    Nair, LG
    George, TG
    Augustine, A
    [J]. TETRAHEDRON, 2000, 56 (38) : 7607 - 7611
  • [15] Cerium(IV) ammonium nitrate - A versatile single-electron oxidant
    Nair, Vijay
    Deepthi, Ani
    [J]. CHEMICAL REVIEWS, 2007, 107 (05) : 1862 - 1891
  • [16] REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF UNSATURATED CARBONYL-COMPOUNDS BASED ON CERIC AMMONIUM NITRATE-PROMOTED OXIDATIVE ADDITION OF TRIMETHYLSILYL ENOL ETHERS TO CONJUGATED DIENES
    PAOLOBELLI, AB
    CECCHERELLI, P
    PIZZO, F
    RUZZICONI, R
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (15) : 4954 - 4958
  • [17] A simple and fast procedure for efficient synthesis of β- and γ-azidoarylketones
    Singh, PND
    Muthukrishnan, S
    Murthy, RS
    Klima, RF
    Mandel, SM
    Hawk, M
    Yarbrough, N
    Gudmundsdóttir, AD
    [J]. TETRAHEDRON LETTERS, 2003, 44 (51) : 9169 - 9171
  • [18] UCHIDA M, 1989, CHEM PHARM BULL, V37, P958
  • [19] 2-PHENYLPYRROLES AS CONFORMATIONALLY RESTRICTED BENZAMIDE ANALOGS - A NEW CLASS OF POTENTIAL ANTIPSYCHOTICS .2.
    VANWIJNGAARDEN, I
    KRUSE, CG
    VANDERHEYDEN, JAM
    TULP, MTM
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (10) : 1934 - 1940
  • [20] Solvent-dependent chemoselectivities in additions of β-carbonyl imines to allyltrimethylsilane with CTAN
    Zhang, Y
    Raines, AJ
    Flowers, RA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (19) : 6267 - 6272