Thioamide-Directed Cp*Co(III)-Catalyzed C-H Allylation of Ferrocenes

被引:28
作者
Zhang, Zhuo-Zhuo [1 ]
Liao, Gang [2 ]
Chen, Hao-Ming [2 ]
Shi, Bing-Feng [2 ,3 ,4 ]
机构
[1] Chengdu Univ, Sch Food & Biol Engn, Chengdu 610106, Sichuan, Peoples R China
[2] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China
[3] Zhengzhou Univ, Green Catalysis Ctr, Zhengzhou 450001, Peoples R China
[4] Zhengzhou Univ, Coll Chem, Zhengzhou 450001, Peoples R China
关键词
PLANAR CHIRAL FERROCENES; COBALT(III)-CATALYZED ALLYLATION; BOND FUNCTIONALIZATION; AMIDATION; ARYLATION; ACTIVATION; KETONES;
D O I
10.1021/acs.orglett.1c00533
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, the first Cp*Co(III)-catalyzed C-H allylation of ferrocene thioamides with allyl carbonates has been developed. This reaction is compatible with a wide range of functional groups, providing various allylated ferrocene derivatives in up to 90% yields. In addition, the C-H allylation protocol is also compatible with the use of vinylcyclopropanes as allylating reagents by merging C-H and C-C activation into one catalytic system. Mechanistic studies revealed that the thiocarbonyl-directing group plays a vital role in C-H activation.
引用
收藏
页码:2626 / 2631
页数:6
相关论文
共 50 条
  • [31] Cp*Co(III)-Catalyzed C-H Hydroarylation of Alkynes and Alkenes and Beyond: A Versatile Synthetic Tool
    Carral-Menoyo, Asier
    Sotomayor, Nuria
    Lete, Esther
    ACS OMEGA, 2020, 5 (39): : 24974 - 24993
  • [32] Rhodium(III)-Catalyzed C-H Alkynylation of Ferrocenes with Hypervalent Iodine Reagents
    Wang, Shao-Bo
    Gu, Qing
    You, Shu-Li
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (22) : 11829 - 11835
  • [33] Manganese(I)-Catalyzed C-H Allylation of Tryptophans and Their Oligopeptides On Water
    Struwe, Julia
    Oyama, Tsuyoshi
    Gallou, Fabrice
    Ackermann, Lutz
    SYNLETT, 2024, 35 (08) : 903 - 907
  • [34] Co(III)-Catalyzed Enaminone-Directed C-H Amidation for Quinolone Synthesis
    Shi, Pengfei
    Wang, Lili
    Chen, Kehao
    Wang, Jie
    Zhu, Jin
    ORGANIC LETTERS, 2017, 19 (09) : 2418 - 2421
  • [35] Achiral CpxIr(III)/Chiral Carboxylic Acid Catalyzed Enantioselective C-H Amidation of Ferrocenes under Mild Conditions
    Liu, Lei
    Song, Hong
    Liu, Yan-Hua
    Wu, Le-Song
    Shi, Bing-Feng
    ACS CATALYSIS, 2020, 10 (13) : 7117 - 7122
  • [36] Ruthenium(II)-Catalyzed S(II)-Directed Aromatic C-H Allylation with Vinylaziridines
    Duan, Yu-Tong
    Wang, Zhong-Xia
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (23) : 16076 - 16090
  • [37] Cp∗Co(III)-catalyzed C-H amidation of 2-arylimidazo[1,2-α]pyridines with dioxazolones
    Yu, Yongqi
    Bai, Jinjin
    You, Mengdan
    Yu, Jiajia
    Li, Wenguang
    Xiao, Yuanjiu
    Zhang, Shiyu
    Xiong, Zhenhua
    Tan, Ze
    TETRAHEDRON, 2025, 171
  • [38] Synthesis of Benzofulvenes via Cp*Co(III)-Catalyzed C-H Activation and Carbocyclization of Aromatic Ketones with Internal Alkynes
    Yu, Yongqi
    Wu, Qianlong
    Liu, Da
    Hu, Liang
    Yu, Lin
    Tan, Ze
    Zhu, Gangguo
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (11) : 7449 - 7458
  • [39] Mild Rhodium(III)-Catalyzed Direct C-H Allylation of Arenes with Allyl Carbonates
    Wang, Honggen
    Schroeder, Nils
    Glorius, Frank
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (20) : 5386 - 5389
  • [40] Cp*Co(III)-Catalyzed C-H Acylmethylation of Arenes by Employing Sulfoxonium Ylides as Carbene Precursors
    Ji, Shuying
    Yan, Kelu
    Li, Bin
    Wang, Baiquan
    ORGANIC LETTERS, 2018, 20 (18) : 5981 - 5984