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

被引:25
|
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
  • [21] 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
  • [22] Ru(ii)-catalyzed C-H alkynylation of ferrocenes with bromoalkynes directed by carboxamide groups
    Zhao, Ru-Yuan
    Zhang, Jing
    Niu, Rui-Han
    Li, Jin-Heng
    Sun, Bo
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (08) : 2007 - 2012
  • [23] 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
  • [24] Cp*Co(III)-catalyzed ortho C-H amidation of 2-pyridinyl ferrocenes with 1,4,2-dioxazol-5-ones
    Wang, Shao-Bo
    Gu, Qing
    You, Shu-Li
    JOURNAL OF CATALYSIS, 2018, 361 : 393 - 397
  • [25] Rhodium(ii)-catalyzed C-H carboxylation of ferrocenes with CO2
    Lv, Hong
    Wang, Xinchao
    Hao, Yanzhao
    Ma, Chao
    Li, Shangda
    Li, Gang
    Zhang, Jian
    GREEN CHEMISTRY, 2023, 25 (02) : 554 - 559
  • [26] Rhodium(III)-catalyzed heteroatom-directed C-H allylation with allylic phosphonates and allylic carbonates at room temperature
    Jo, Hyeim
    Han, Sangil
    Park, Jihye
    Choi, Miji
    Han, Sang Hoon
    Jeong, Taejoo
    Lee, Seok-Yong
    Kwak, Jong Hwan
    Jung, Young Hoon
    Kim, In Su
    TETRAHEDRON, 2016, 72 (04) : 571 - 578
  • [27] Thiocarbamate-directed Cp*Co(III)-Catalyzed Olefinic C-H Amidation: Facile Access to Enamines with High (Z)-Selectivity
    Liang, Ya-Ru
    Si, Xiao-Ju
    Zhang, He
    Yang, Dandan
    Niu, Jun-Long
    Song, Mao-Ping
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (04) : 694 - 700
  • [28] 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
  • [29] Thioketone-directed rhodium(I) catalyzed enantioselective C-H bond arylation of ferrocenes
    Zhong-Jian Cai
    Chen-Xu Liu
    Qiang Wang
    Qing Gu
    Shu-Li You
    Nature Communications, 10
  • [30] Thioketone-directed rhodium(I) catalyzed enantioselective C-H bond arylation of ferrocenes
    Cai, Zhong-Jian
    Liu, Chen-Xu
    Wang, Qiang
    Gu, Qing
    You, Shu-Li
    NATURE COMMUNICATIONS, 2019, 10 (1)