Pd(II)-Catalyzed Direct Sulfonylation of Unactivated C(sp3)-H Bonds with Sodium Sulfinates

被引：107
|
作者：
Rao, Wei-Hao [1 ]
Zhan, Bei-Bei [1 ]
Chen, Kai [1 ]
Ling, Peng-Xiang [1 ]
Zhang, Zhuo-Zhuo [1 ]
Shi, Bing-Feng [1 ]
机构：
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 14期
关键词：
C-S BOND; CATALYZED DIRECT THIOLATION; EFFICIENT SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; C(SP(2))-H BONDS; TERMINAL ALKYNES; ARYL HALIDES; ARYLATION; FUNCTIONALIZATION; ALKYLATION;
D O I：
10.1021/acs.orglett.5b01634
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Pd(II)-catalyzed sulfonylation of unactivated C(sp(3))-H bonds with sodium arylsulfinates using an 8-aminoquinoline auxiliary is described. This reaction demonstrates excellent functional group tolerance with respect to both the caboxamide starting material and the sodium arylsulfinate coupling partner, affording a broad range of aryl alkyl sulfones. Moreover, the late-stage modification of complex molecules was achieved via this sulfonylation protocol.
引用
收藏
页码：3552 / 3555
页数：4
相关论文
共 50 条
  • [21] Transition metal-catalyzed arylation of unactivated C(sp3)-H bonds
    Baudoin, Olivier
    CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 4902 - 4911
  • [22] Palladium-catalyzed oxygenation of unactivated sp3 C-H bonds
    1600, American Chemical Society, Columbus, United States (126):
  • [23] Rhodium-Catalyzed Intramolecular Silylation of Unactivated C(sp3)-H Bonds
    Kuninobu, Yoichiro
    Nakahara, Takahiro
    Takeshima, Hirotaka
    Takai, Kazuhiko
    ORGANIC LETTERS, 2013, 15 (02) : 426 - 428
  • [24] PdII-Catalyzed Intermolecular Amination of Unactivated C(sp3)H Bonds
    Gou, Quan
    Liu, Gang
    Liu, Zi-Ning
    Qin, Jun
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (44) : 15491 - 15495
  • [25] Direct coupling of unactivated alkynes and C(sp3)-H bonds catalyzed by a Pt(II, IV)-centered catalyst: a computational study
    Li, Zhi-Feng
    Li, Hui-Xue
    Yang, Xiao-Ping
    Liu, Xin-Wen
    Zuo, Guo-Fang
    Zhao, Cunyuan
    RSC ADVANCES, 2015, 5 (40) : 31954 - 31964
  • [26] Iodine-catalysed sp3 C-H sulfonylation to form β-dicarbonyl sulfones with sodium sulfinates
    Gao, Wen-Chao
    Zhao, Jin-Jin
    Chang, Hong-Hong
    Li, Xing
    Liu, Qiang
    Wei, Wen-Long
    RSC ADVANCES, 2014, 4 (90): : 49329 - 49332
  • [27] -Lactone Synthesis via Palladium(II)-Catalyzed Lactonization of Unactivated Methylene C(sp3)-H Bonds
    Liu, Bin
    Shi, Bing-Feng
    SYNLETT, 2016, 27 (16) : 2396 - 2400
  • [28] Catalytic fluorination of unactivated C(sp3)-H bonds
    Ma, Jun-An
    Li, Shen
    ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (06): : 712 - 715
  • [29] Stereoselective alkoxycarbonylation of unactivated C(sp3)-H bonds with alkyl chloroformates via Pd(II)/Pd(IV) catalysis
    Liao, Gang
    Yin, Xue-Song
    Chen, Kai
    Zhang, Qi
    Zhang, Shuo-Qing
    Shi, Bing-Feng
    NATURE COMMUNICATIONS, 2016, 7
  • [30] Stereoselective alkoxycarbonylation of unactivated C(sp3)–H bonds with alkyl chloroformates via Pd(II)/Pd(IV) catalysis
    Gang Liao
    Xue-Song Yin
    Kai Chen
    Qi Zhang
    Shuo-Qing Zhang
    Bing-Feng Shi
    Nature Communications, 7
12345