Rhodium(III)-Catalyzed Synthesis of Skipped Enynes via C(sp3)-H Alkynylation of Terminal Alkenes

被引：18
|
作者：
Della-Felice, Franco [1 ]
Zanini, Margherita [1 ]
Jie, Xiaoming [1 ]
Tan, Eric [1 ]
Echavarren, Antonio M. [1 ]
机构：
[1] Barcelona Inst Sci & Technol, Inst Chem Res Catalonia ICIQ, Ave Paisos Catalans 16, Tarragona 43007, Spain
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2021年 / 60卷 / 11期
基金：
欧盟地平线“2020”;
关键词：
1,4-enynes; alkynylation; allylic functionalization; rhodium; undirected C-H activation;
D O I：
10.1002/anie.202014877
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The Rh-III-catalyzed allylic C-H alkynylation of non-activated terminal alkenes leads selectively to linear 1,4-enynes at room-temperature. The catalytic system tolerates a wide range of functional groups without competing functionalization at other positions. Similarly, the vinylic C-H alkynylation of alpha,beta- and beta,gamma- unsaturated amides gives conjugated Z-1,3-enynes and E-enediynes.
引用
收藏
页码：5693 / 5698
页数：6
相关论文
共 50 条
  • [1] Rhodium(III)-Catalyzed Intermolecular Amidation with Azides via C(sp3)-H Functionalization
    Wang, Nuancheng
    Li, Renhe
    Li, Liubo
    Xu, Shansheng
    Song, Haibin
    Wang, Baiquan
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (11): : 5379 - 5385
  • [2] Terminal C(sp3)-H alkylation of internal alkenes via Ni/H-catalyzed isomerization
    Wang, Zhen-Yu
    Wan, Jia-Hao
    Wang, Gao-Yin
    Wang, Rui
    Jin, Ruo-Xing
    Lan, Quan
    Wang, Xi-Sheng
    TETRAHEDRON LETTERS, 2018, 59 (23) : 2302 - 2305
  • [3] Rhodium(III)-Catalyzed C(sp3)-H Bond Aminocarbonylation with Isocyanates
    Zhao, Huaiqing
    Zhou, Xi
    Li, Bo
    Liu, Xiufen
    Guo, Ningxin
    Lu, Zhengliang
    Wang, Shoufeng
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (07): : 4153 - 4159
  • [4] Rhodium(III)-Catalyzed Amidation of Unactivated C(sp3)H Bonds
    Wang, He
    Tang, Guodong
    Li, Xingwei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (44) : 13049 - 13052
  • [5] Rhodium(III)-Catalyzed Acylation of C(sp3)-H Bonds with Cyclopropenones
    Kong, Lingheng
    Zhou, Xukai
    Xu, Youwei
    Li, Xingwei
    ORGANIC LETTERS, 2017, 19 (13) : 3644 - 3647
  • [6] Palladium(0)-Catalyzed Alkynylation of C(sp3)-H Bonds
    He, Jian
    Wasa, Masayuki
    Chan, Kelvin S. L.
    Yu, Jin-Quan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (09) : 3387 - 3390
  • [7] Palladium(0)-Catalyzed Alkynylation of C(sp3)-H Bonds
    Yu, Jin-Quan
    He, Jian
    SYNTHESIS-STUTTGART, 2013, 45 (11): : A77 - A78
  • [8] Synthesis of β-alkynyl α-amino acids via palladium-catalyzed alkynylation of unactivated C(sp3)-H bonds
    Bo Wang
    Gang He
    Gong Chen
    Science China Chemistry, 2015, 58 : 1345 - 1348
  • [9] Synthesis of β-alkynyl α-amino acids via palladium-catalyzed alkynylation of unactivated C(sp3)-H bonds
    Wang, Bo
    He, Gang
    Chen, Gong
    SCIENCE CHINA-CHEMISTRY, 2015, 58 (08) : 1345 - 1348
  • [10] Rhodium(III)-catalyzed alkyllation of primary C(sp3)-H bonds with α-diazocarbonyl compounds
    Hou, Wei
    Yang, Yaxi
    Wu, Yunxiang
    Feng, Huijin
    Li, Yuanchao
    Zhou, Bing
    CHEMICAL COMMUNICATIONS, 2016, 52 (62) : 9672 - 9675
12345