Phosphine-Free Suzuki-Miyaura Cross-Coupling in Aqueous Media Enables Access to 2-C-Aryl-Glycosides

被引：63
|
作者：
Cobo, Isidro [1 ,2 ]
Matheu, M. Isabel [2 ]
Castillon, Sergio [2 ]
Boutureira, Omar [1 ,2 ]
Davis, Benjamin G. [1 ]
机构：
[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England
[2] Univ Rovira & Virgili, Dept Quim Analit & Quim Organ, Tarragona 43007, Spain
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 07期
基金：
英国工程与自然科学研究理事会; 英国生物技术与生命科学研究理事会;
关键词：
C-GLYCOSIDE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ARYL GLYCOSIDES; GLYCOSYLTRANSFERASE INHIBITORS; CARBOHYDRATE-CHEMISTRY; PERACETYLATED GLYCALS; EFFICIENT SYNTHESIS; ARYLBORONIC ACIDS; ORGANIC-SYNTHESIS; EXO-GLYCALS;
D O I：
10.1021/ol3003139
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A general strategy for the synthesis of 2-aryl-glycals and their elaboration to 2-C-aryl-alpha-glycosides and 1,5-anhydro-2-C-ary1-2-deoxy alditols are described. The use of reliable, efficient phosphine-free Suzuki-Miyaura cross-coupling of 2-iodoglycals in aqueous media as a key step proceeds with complete regioselectivity at C-2 and enables access to 2-aryl-glycals with different configurations in excellent yields.
引用
收藏
页码：1728 / 1731
页数：4
相关论文
共 50 条
  • [1] Ferrocenylimidazoline palladacycles: efficient phosphine-free catalysts for Suzuki-Miyaura cross-coupling reaction
    Ma, Ji
    Cui, Xiuling
    Zhang, Bi
    Song, Maoping
    Wu, Yangjie
    [J]. TETRAHEDRON, 2007, 63 (25) : 5529 - 5538
  • [2] Towards phosphine-free Pd(II) pincer complexes for catalyzing Suzuki-Miyaura cross-coupling reaction in aqueous medium
    Jerome, Peter
    Sathishkumar, Pushpanathan N.
    Bhuvanesh, Nattamai S. P.
    Karvembu, Ramasamy
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2017, 845 : 115 - 124
  • [3] Supported phosphine-free palladium catalysts for the Suzuki-Miyaura reaction in aqueous media
    Phan, Nam T. S.
    Styring, Peter
    [J]. GREEN CHEMISTRY, 2008, 10 (10) : 1055 - 1060
  • [4] Suzuki-Miyaura Cross-Coupling of Potassium Alkoxyethyltrifluoroborates: Access to Aryl/Heteroarylethyloxy Motifs
    Fleury-Bregeot, Nicolas
    Presset, Marc
    Beaumard, Floriane
    Colornbel, Virginie
    Oehlrich, Daniel
    Rombouts, Frederik
    Molander, Gary A.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22): : 10399 - 10408
  • [5] Pd(OAc)2@SBA-15/PrEn nanoreactor: a highly active, reusable and selective phosphine-free catalyst for Suzuki-Miyaura cross-coupling reaction in aqueous media
    Rostamnia, Sadegh
    Xin, Hongchuan
    [J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2013, 27 (06) : 348 - 352
  • [6] Synthesize, Characterization and Application of Phosphine-free Polymer Supported Palladium Nanoparticles as Effective Catalyst in Suzuki-Miyaura Cross-coupling Reactions
    Mahdavi, Hossein
    Hashemi, Payam
    [J]. JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2013, 60 (04) : 425 - 436
  • [7] Unexpected base dependence in aqueous Suzuki-Miyaura cross-coupling
    Buxton, Audrey M.
    Hamilton, Alaina E.
    Chalker, Justin M.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [8] A Convenient Catalyst for Aqueous and Protein Suzuki-Miyaura Cross-Coupling
    Chalker, Justin M.
    Wood, Charlotte S. C.
    Davis, Benjamin G.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (45) : 16346 - +
  • [9] Aqueous Suzuki-Miyaura cross-coupling for the undergraduate teaching lab
    Hamilton, Alaina E.
    Buxton, Audrey M.
    Chalker, Justin M.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [10] Phosphine-free Suzuki cross-coupling reactions under ultrasound
    Silva, Aires da Conceicao
    de Souza, Andria Luzia F.
    Antunes, O. A. C.
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2007, 692 (14) : 3104 - 3108
12345