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
  • [31] Catalytic alkylation of unactivated C(sp3)-H bonds for C(sp3)-C(sp3) bond formation
    Chen, Zhen
    Rong, Meng-Yu
    Nie, Jing
    Zhu, Xue-Feng
    Shi, Bing-Feng
    Ma, Jun-An
    CHEMICAL SOCIETY REVIEWS, 2019, 48 (18) : 4921 - 4942
  • [32] Pd(II)-Catalyzed Intermolecular Arylation of Unactivated C(sp3)-H Bonds with Aryl Bromides Enabled by 8-Aminoquinoline Auxiliary
    Wei, Yu
    Tang, Huarong
    Cong, Xuefeng
    Rao, Bin
    Wu, Chao
    Zeng, Xiaoming
    ORGANIC LETTERS, 2014, 16 (08) : 2248 - 2251
  • [33] Pd-catalyzed arylation of Sp3 C-H bonds
    Daugulis, Olafs
    Khan, Rana Kashif M.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233 : 132 - 132
  • [34] Copper-Catalyzed, Interrupted Remote Fluoromethylthiolation of Unactivated C(sp3)-H Bonds
    Yu, Fan
    Wang, Wengui
    Wang, Shoufeng
    ORGANIC LETTERS, 2024, 26 (10) : 2068 - 2072
  • [35] Recent Advances in Copper-Catalyzed Functionalization of Unactivated C(sp3)-H Bonds
    Deshpande, Neha
    Satani, Piyushkumar
    Bharodiya, Akshay
    Naveen, Togati
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (12)
  • [36] Pd(II)-catalyzed alkoxylation of unactivated C(sp3)-H and C(sp2)-H bonds using a removable directing group: efficient synthesis of alkyl ethers
    Chen, Fa-Jie
    Zhao, Sheng
    Hu, Fang
    Chen, Kai
    Zhang, Qi
    Zhang, Shuo-Qing
    Shi, Bing-Feng
    CHEMICAL SCIENCE, 2013, 4 (11) : 4187 - 4192
  • [37] Pd(II)-Catalyzed Chemoselective Acetoxylation of C(sp2)-H and C(sp3)-H Bonds in Tertiary Amides
    Vijaykumar, Muniyappa
    Punji, Benudhar
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (12): : 8172 - 8181
  • [38] Ligand-Enabled Pd(II)-Catalyzed Bromination and Iodination of C(sp3)-H Bonds
    Zhu, Ru-Yi
    Saint-Denis, Tyler G.
    Shao, Ying
    He, Jian
    Sieber, Joshua D.
    Senanayake, Chris H.
    Yu, Jin-Quan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (16) : 5724 - 5727
  • [39] Pd(II)-Catalyzed Enantioselective C(sp3)-H Borylation
    He, Jian
    Shao, Qian
    Wu, Qingfeng
    Yu, Jin-Quan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (09) : 3344 - 3347
  • [40] Visible-light-induced copper-catalyzed regiodivergent C(sp3)-sulfonylation of oxime esters with sodium sulfinates
    Ma, Ben
    Chen, Zhiyong
    Ma, Min
    Zhao, Zheng
    Long, Yun'e
    Chen, Dongping
    Yang, Jingya
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (20): : 5876 - 5883
12345