Palladium-Catalyzed α-Arylation of Benzylic Phosphonates

被引：45
作者：
Montel, Sonia [1 ]
Raffier, Ludovic [1 ]
He, Yuying [1 ]
Walsh, Patrick J. [1 ]
机构：
[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Penn Merck Lab High Throughput Expt, Philadelphia, PA 19104 USA
来源：
ORGANIC LETTERS | 2014年 / 16卷 / 05期
基金：
美国国家科学基金会; 美国国家卫生研究院;
关键词：
CARBANIONS; SULFOXIDES; COMPLEXES; AMIDES;
D O I：
10.1021/ol5002413
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new synthetic route to access diarylmethyl phosphonates is presented. The transformation enables the introduction of aromatic groups on benzylic phosphonates via a deprotonative cross-coupling process (DCCP). The Pd(OAc)(2)/CataCXium A-based catalyst afforded a reaction between benzyl diisopropyl phosphonate derivatives and aryl bromides in good to excellent isolated yields (64-92%).
引用
收藏
页码：1446 / 1449
页数：4
相关论文
共 35 条
  • [1] Photochemical vinylcyclopropane rearrangements of 1-substituted-3-(2,2-diphenylvinyl)-2,2-dimethylcyclopropanes to cyclopentenes and different heterocycles
    Armesto, D
    Ortiz, MJ
    Agarrabeitia, AR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) : 1056 - 1060
  • [2] Arrachart G., 2013, Patent, Patent No. [WO2013167516 A1 20131114, 201316716]
  • [3] Additive effects on palladium-catalyzed deprotonative-cross-coupling processes (DCCP) of sp3 C-H bonds in diarylmethanes
    Bellomo, Ana
    Zhang, Jiadi
    Trongsiriwat, Nisalak
    Walsh, Patrick J.
    [J]. CHEMICAL SCIENCE, 2013, 4 (02) : 849 - 857
  • [4] BIELLMANN JF, 1982, ORG REACTIONS, V27, P1
  • [5] Bisceglia JA, 2012, CURR ORG CHEM, V16, P2206
  • [6] Review on Modern Advances of Chemical Methods for the Introduction of a Phosphonic Acid Group
    Demmer, Charles S.
    Krogsgaard-Larsen, Niels
    Bunch, Lennart
    [J]. CHEMICAL REVIEWS, 2011, 111 (12) : 7981 - 8006
  • [7] Georlette P., 2013, Patent, Patent No. [WO2013176868 A1 20131128, 2013176868]
  • [8] Zn(tmp)2:: A versatile base for the selective functionalization of C-H bonds
    Hlavinka, Mark L.
    Hagadorn, John R.
    [J]. ORGANOMETALLICS, 2007, 26 (17) : 4105 - 4108
  • [9] Jackson ER, 2012, CURR TOP MED CHEM, V12, P706
  • [10] Diaryl Sulfoxides from Aryl Benzyl Sulfoxides: A Single PalladiumCatalyzed Triple Relay Process
    Jia, Tiezheng
    Bellomo, Ana
    Montel, Sonia
    Zhang, Mengnan
    Baina, Kawtar E. L.
    Zheng, Bing
    Walsh, Patrick J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (01) : 260 - 264
1234