N,N′-Mono substituted acyclic thioureas: efficient ligands for the palladium catalyzed Heck reaction of deactivated aryl bromides

被引:9
|
作者
Keesara, Srinivas [1 ]
Parvathaneni, Saiprathima [1 ]
Mandapati, Mohan Rao [1 ]
机构
[1] Indian Inst Chem Technol, I&PC Div, Hyderabad 500607, Andhra Pradesh, India
关键词
Thiourea; Heck reaction; Phosphine free; Palladium; N-HETEROCYCLIC CARBENES; CROSS-COUPLING REACTION; SUZUKI REACTIONS; COMPLEXES; PD; PD(II); ACID;
D O I
10.1016/j.tetlet.2014.09.053
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of N,N'-mono substituted acyclic thiourea ligands are found to be highly active phosphine-free catalysts for palladium catalyzed Heck reaction of aryl iodides and bromides with olefins. We have achieved high turnover numbers for aryl iodides with olefins (TONS up to 970,000 for the reaction of iodobenzene with styrene). (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6769 / 6772
页数:4
相关论文
共 50 条
  • [1] Palladium-catalyzed Heck reaction of aryl bromides in aqueous media using tris(N-heterocyclic carbene) ligands
    Ozdemir, Ismail
    Demir, Serpil
    Cetinkaya, Bekir
    SYNLETT, 2007, (06) : 889 - 892
  • [2] Palladium-Catalyzed Carbonylation of Aryl Bromides with N-Substituted Cyanamides
    Lian, Zhong
    Friis, Stig D.
    Lindhardt, Anders T.
    Skrydstrup, Troels
    SYNLETT, 2014, 25 (09) : 1241 - 1245
  • [3] Palladium/tetraphosphine catalysed heck reaction with ortho-substituted aryl bromides
    Feuerstein, M
    Doucet, H
    Santelli, M
    SYNLETT, 2001, (12) : 1980 - 1982
  • [4] Palladium-catalyzed amination of aryl bromides: Use of phosphinoether ligands for the efficient coupling of acyclic secondary amines
    Marcoux, JF
    Wagaw, S
    Buchwald, SL
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (06): : 1568 - 1569
  • [5] Palladium-Catalyzed Heck Coupling Reaction of Aryl Bromides in Aqueous Media Using Tetrahydropyrimidinium Salts as Carbene Ligands
    Yasar, Sedat
    Ozcan, Emine Ozge
    Gurbuz, Nevin
    Cetinkaya, Bekir
    Ozdemir, Ismail
    MOLECULES, 2010, 15 (02): : 649 - 659
  • [6] First efficient palladium-catalyzed Heck reactions of aryl bromides with alkyl methacrylate
    Beller, M
    Riermeier, TH
    TETRAHEDRON LETTERS, 1996, 37 (36) : 6535 - 6538
  • [7] PALLADIUM CATALYZED REACTION OF HEXABUTYLDITIN WITH ARYL BROMIDES - PREPARATION OF NEGATIVELY SUBSTITUTED ARYLTRIBUTYLTIN
    KOSUGI, M
    SHIMIZU, K
    OHTANI, A
    MIGITA, T
    CHEMISTRY LETTERS, 1981, (06) : 829 - 830
  • [8] N,N-dimethyl-β-alanine as an inexpensive and efficient ligand for palladium-catalyzed Heck reaction
    Cui, Xin
    Li, Zhe
    Tao, Chuan-Zhou
    Xu, Yu
    Li, Juan
    Liu, Lei
    Guo, Qing-Xiang
    ORGANIC LETTERS, 2006, 8 (12) : 2467 - 2470
  • [9] Palladium-Catalyzed Heck Reaction of Polyoxometalate-Functionalised Aryl Iodides and Bromides with Olefins
    Zhu, Yulin
    Wang, Longsheng
    Hao, Jian
    Yin, Panchao
    Zhang, Jin
    Li, Qiang
    Zhu, Li
    Wei, Yongge
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (13) : 3076 - 3080
  • [10] N4-Tetradentate Dicarboxyamidate/Dipyridyl Palladium Complexes as Robust Catalysts for the Heck Reaction of Deactivated Aryl Chlorides
    Srinivas, Pottabathula
    Likhar, Pravin R.
    Maheswaran, Hariharasarma
    Sridhar, Balasubramanian
    Ravikumar, Krishnan
    Kantam, Mannepalli Lakshmi
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (07) : 1578 - 1581