One-pot palladium-catalyzed phosphination of aryl iodides with Ph2PSnR3

被引:26
|
作者
Martín, SE [1 ]
Bonaterra, M [1 ]
Rossi, RA [1 ]
机构
[1] Univ Nacl Cordoba, Fac Ciencias Quim, Dept Quim Organ, INFIQC, RA-5000 Cordoba, Argentina
关键词
tertiary phosphines; palladium catalysis; P-C cross-coupling;
D O I
10.1016/S0022-328X(02)02014-4
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
We found a very efficient one-pot phosphination reaction starting with Ph3P, which by reaction with Na metal in liquid ammonia gives Ph2P- ions that reacted with R3SnCl to afford (trialkylstannyl)diphenylphosphine. The palladium-catalyzed coupling reaction of these stannanes with aryl iodides yield functionalized phosphines in high yield (69-97%). The use of Ph3P as starting reagent, the endurance of the reaction to a wide variety of functional groups and the easiness of a one-pot reaction make this method a useful and versatile approach to tertiary phosphine oxides. (C) 2002 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:223 / 227
页数:5
相关论文
共 50 条
  • [41] A ONE-POT PALLADIUM-CATALYZED SYNTHESIS OF BETA,BETA-DIARYLKETONES AND ALDEHYDES FROM ARYL IODIDES AND ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS
    CACCHI, S
    PALMIERI, G
    SYNTHESIS-STUTTGART, 1984, (07): : 575 - 577
  • [42] One-pot synthesis of diaryl ketones from aldehydes via palladium-catalyzed reaction with aryl boronic acids
    Qin, Changming
    Chen, Jiuxi
    Wu, Huayue
    Cheng, Jiang
    Zhang, Qiang
    Zuo, Bing
    Su, Weike
    Ding, Jinchang
    TETRAHEDRON LETTERS, 2008, 49 (11) : 1884 - 1888
  • [43] One-Pot Synthesis of Unsymmetrical Diaryl Thioethers by Palladium-Catalyzed Coupling of Two Aryl Bromides and a Thiol Surrogate
    Fernandez-Rodriguez, Manuel A.
    Hartwig, John F.
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (08) : 2355 - 2359
  • [44] Facile One-Pot Palladium-Catalyzed Sequential Coupling to Diarylmethanes by Using Aryl Methyl Ketones as the Methylene Donors
    Wang, Xing
    Liu, Lian-Hua
    Shi, Jin-Hua
    Peng, Ji
    Tu, Hai-Yang
    Zhang, Ai-Dong
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (30) : 6870 - 6877
  • [45] PALLADIUM-CATALYZED CARBONYLATION OF ARYL IODIDES IN AQUEOUS-MEDIA
    BUMAGIN, NA
    NIKITIN, KV
    BELETSKAYA, IP
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 358 (1-3) : 563 - 565
  • [46] Palladium-Catalyzed Coupling of Hydroxylamines with Aryl Bromides, Chlorides, and Iodides
    Porzelle, Achim
    Woodrow, Michael D.
    Tomkinson, Nicholas C. O.
    ORGANIC LETTERS, 2009, 11 (01) : 233 - 236
  • [47] Palladium-catalyzed cascade reaction of α,β-unsaturated sulfones with aryl iodides
    Mauleón, P
    Núñez, AA
    Alonso, I
    Carretero, JC
    CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (07) : 1511 - 1520
  • [48] Unexpected regioselectivity in the palladium-catalyzed reaction of silacyclobutanes with aryl iodides
    Tanaka, Y
    Nishigaki, A
    Kimura, Y
    Yamashita, M
    APPLIED ORGANOMETALLIC CHEMISTRY, 2001, 15 (08) : 667 - 670
  • [49] STYRENE DERIVATIVES VIA PALLADIUM-CATALYZED VINYLATION OF ARYL IODIDES
    HALLBERG, A
    WESTERLUND, C
    CHEMISTRY LETTERS, 1982, (12) : 1993 - 1994
  • [50] Palladium-Catalyzed Formylation of Aryl Iodides with HCOOH as CO Source
    Sun, Guanglong
    Lv, Xue
    Zhang, Yinan
    Lei, Min
    Hu, Lihong
    ORGANIC LETTERS, 2017, 19 (16) : 4235 - 4238