Synthesis of arylstannanes by palladium-catalyzed desulfitative coupling reaction of sodium arylsulfinates with distannanes

被引：9
|
作者：
Lian, Chang [1 ]
Yue, Guanglu [1 ]
Zhang, Haonan [1 ]
Wei, Liyan [1 ]
Liu, Danyang [1 ]
Liu, Sichen [1 ]
Fang, Huayi [2 ]
Qiu, Di [1 ]
机构：
[1] Tianjin Normal Univ, Minist Educ, Key Lab Inorgan Organ Hybrid Funct Mat Chem, Coll Chem,Tianjin Key Lab Struct & Performance Fu, Tianjin 300387, Peoples R China
[2] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China
来源：
TETRAHEDRON LETTERS | 2018年 / 59卷 / 45期
基金：
中国国家自然科学基金;
关键词：
Palladium catalysis; Desulfitative; Cross-coupling; Sodium arylsulfinates; Arylstannane; ARYL SULFINIC ACIDS; DIRECT ESI-MS; ORGANIC HALIDES; BOND-CLEAVAGE; MEDIATED FLUORINATION; ORGANOTIN COMPOUNDS; ALLYLTIN COMPOUNDS; CARBON BOND; ARYLATION; KETONES;
D O I：
10.1016/j.tetlet.2018.09.065
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel Pd-catalyzed desulfitative cross-coupling reaction of sodium arylsulfinates with hexaalkyl distannanes is realized, allowing the facile synthesis of functionalized arylstannanes with moderate to excellent yields. The successful implement of gram-scale synthesis and tandem Stille coupling reaction demonstrates the potential applications of this method in organic synthesis. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4019 / 4023
页数：5
相关论文
共 50 条
  • [1] Palladium-catalyzed desulfitative arylation of sulfonamides with sodium arylsulfinates
    Zhao, Zijian
    Lian, Yan
    Zhao, Chang
    Wang, Bing
    SYNTHETIC COMMUNICATIONS, 2018, 48 (12) : 1436 - 1442
  • [2] Palladium-Catalyzed Desulfitative Cross-Coupling Reaction of Sodium Arylsulfinates with H-Phosphonate Diesters
    Miao, Tao
    Wang, Lei
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (05) : 967 - 971
  • [3] A highly efficient palladium-catalyzed desulfitative arylation of azoles with sodium arylsulfinates
    Wang, Min
    Li, Dengke
    Zhou, Wei
    Wang, Lei
    TETRAHEDRON, 2012, 68 (07) : 1926 - 1930
  • [4] Palladium-catalyzed desulfitative cross-coupling of arylsulfinates with arylboronic acids
    Cheng, Kai
    Yu, Hai-Zhu
    Zhao, Baoli
    Hu, Sai
    Zhang, Xian-Man
    Qi, Chenze
    RSC ADVANCES, 2014, 4 (101) : 57923 - 57928
  • [5] Palladium-Catalyzed Cascade Desulfitative Arylation of Acetylinic Oximes with Sodium Arylsulfinates
    Li, Jianxiao
    Cen, Liying
    He, Dan
    Zhou, Daohao
    Huang, Songxuan
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (20)
  • [6] Palladium-Catalyzed Desulfitative Cross-Coupling of Sodium Arylsulfinates with Aryl Bromides and Chlorides: An Alternative Convenient Synthesis of Biaryls
    Zhou, Chao
    Li, Yaming
    Lu, Yang
    Zhang, Rong
    Jin, Kun
    Fu, Xinmei
    Duan, Chunying
    CHINESE JOURNAL OF CHEMISTRY, 2013, 31 (10) : 1269 - 1273
  • [7] Palladium-catalyzed desulfitative arylation of 3-haloquinolines with arylsulfinates
    Colomb, Julie
    Billard, Thierry
    TETRAHEDRON LETTERS, 2013, 54 (11) : 1471 - 1474
  • [8] Palladium-catalyzed C-3 desulfitative arylation of indolizines with sodium arylsulfinates and arylsulfonyl hydrazides
    Wang, Chunjie
    Jia, Huali
    Li, Zhiwei
    Zhang, Hui
    Zhao, Baoli
    RSC ADVANCES, 2016, 6 (26) : 21814 - 21821
  • [9] Palladium-Catalyzed Desulfitative Cross-Coupling Reaction of Sodium Sulfinates with Propargylic Carbonates
    Qin, Anni
    Zhu, Guirong
    Chen, Qin
    Qian, Hui
    Ma, Shengming
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (20) : 4656 - 4660
  • [10] Palladium-Catalyzed Desulfitative Cross-Coupling Reaction of Sodium Sulfinates with Benzyl Chlorides
    Zhao, Feng
    Tan, Qi
    Xiao, Fuhong
    Zhang, Shufeng
    Deng, Guo-Jun
    ORGANIC LETTERS, 2013, 15 (07) : 1520 - 1523
12345