Iron-Catalyzed Cross-Dehydrogenative Coupling of Oxindoles with Thiols/Selenols for Direct C(sp3)-S/Se Bond Formation

被引：32
|
作者：
Huang, Lu-Shan [1 ,2 ]
Han, Dong-Yang [1 ,2 ]
Xu, Da-Zhen [1 ,2 ]
机构：
[1] Nankai Univ, Coll Chem, Natl Engn Res Ctr Pesticide Tianjin, State Key Lab, Tianjin 300071, Peoples R China
[2] Nankai Univ, Coll Chem, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2019年 / 361卷 / 17期
基金：
中国国家自然科学基金;
关键词：
Iron; Cross-dehydrogenative coupling; Oxidation; Air; C-S bond formation; C-C BOND; ORGANOCATALYZED SULFENYLATION; 3,3-DISUBSTITUTED OXINDOLES; ASYMMETRIC SULFENYLATION; REGIOSELECTIVE SYNTHESIS; H BONDS; FUNCTIONALIZATION; ACTIVATION; ANTIFUNGAL; PHYTOALEXINS;
D O I：
10.1002/adsc.201900400
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
The C-X (S/Se) bonds are common and ubiquitous in natural products and pharmaceuticals. Here, we report an iron-catalyzed cross-dehydrogenative coupling (CDC) reaction for the direct synthesis of C(sp(3))-X (S/Se) bonds from oxindoles, phenylacetamides, pyrazolones, phenylacetonitriles and ethyl cyanoacetate with thiols and selenols. All the reactions were performed under simple and mild conditions, and air (molecular oxygen) was employed as an ideal green oxidant, thus promising broad application in chemical industry and modification of bioactive molecules.
引用
收藏
页码：4016 / 4021
页数：6
相关论文
共 50 条
  • [41] Copper-catalyzed aerobic asymmetric cross-dehydrogenative coupling of C(sp3)-H bonds driven by visible light
    Zhou, Kexu
    Yu, Ying
    Lin, Yu-Mei
    Li, Yanjun
    Gong, Lei
    GREEN CHEMISTRY, 2020, 22 (14) : 4597 - 4603
  • [42] Iron-catalyzed cross-dehydrogenative C-H amidation of benzofurans and benzothiophenes with anilines
    Ni, Yang
    Wan, Xiang
    Zuo, Honghua
    Bashir, Muhammad Adnan
    Liu, Yu
    Yu, Huaibin
    Liao, Rong-Zhen
    Wu, Guojiao
    Zhong, Fangrui
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (07) : 1490 - 1495
  • [43] Cp*Rh(III)-Catalyzed Cross-Coupling of Alkyltrifluoroborate with α-Diazomalonates for C(sp3)-C(sp3) Bond Formation
    Lu, Yin-Suo
    Yu, Wing-Yiu
    ORGANIC LETTERS, 2016, 18 (06) : 1350 - 1353
  • [44] Copper Porphyrin Catalyzed C(sp3)-H Activation via Cross-Dehydrogenative Coupling: Facile Transformation of Aldehydes to Esters
    Shan, Zi-Wei
    Chen, Xiao-Yan
    Zhang, Hao
    Liu, Hai-Yang
    Yuan, Gao-Qing
    SYNLETT, 2022, 33 (11) : 1075 - 1082
  • [45] Cobalt-Catalyzed Cross-Dehydrogenative Coupling Reaction between Unactivated C(sp2)-H and C(sp3)-H Bonds
    Li, Qun
    Hu, Weipeng
    Hu, Renjian
    Lu, Hongjian
    Li, Guigen
    ORGANIC LETTERS, 2017, 19 (17) : 4676 - 4679
  • [46] Iron-Catalyzed Cross-Dehydrogenative Coupling of para-Quinone Methides with Formamides: In Situ Activation of C(sp2)-H Bonds
    Yuan, Minjing
    Li, Zikang
    Shang, Wenli
    Xiong, Biquan
    Xu, Weifeng
    Zhu, Longzhi
    Liu, Yu
    Tang, Ke-Wen
    Wong, Wai-Yeung
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (22): : 16663 - 16678
  • [47] Cu-catalyzed cross-dehydrogenative coupling:: A versatile strateav for C-C bond formations via the oxidative activation of sp3 C-H bonds
    Li, Zhiping
    Bohle, D. Scott
    Li, Chao-Jun
    PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2006, 103 (24) : 8928 - 8933
  • [48] Applications of copper and iron-catalyzed Csp3–Csp3 cross-dehydrogenative coupling in organic synthesis
    Khalifa Z.
    Patel A.B.
    Synthetic Communications, 2023, 53 (20) : 1665 - 1700
  • [49] An unprecedented tandem synthesis of fluorescent coumarin-fused pyrimidines via copper-catalyzed cross-dehydrogenative C(sp3)-N bond coupling
    Kumari, Santosh
    Shakoor, S. M. Abdul
    Khullar, Sadhika
    Mandal, Sanjay K.
    Sakhuja, Rajeev
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (17) : 3220 - 3228
  • [50] Merging Photoredox with Bronsted Acid Catalysis: The Cross-Dehydrogenative C-O Coupling for sp3 C-H Bond Peroxidation
    Xia, Qing
    Wang, Qiang
    Yan, Changcun
    Dong, Jianyang
    Song, Hongjian
    Li, Ling
    Liu, Yuxiu
    Wang, Qingmin
    Liu, Xiangming
    Song, Haibin
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (45) : 10871 - 10877
12345