Deoxygenative alkynylation of amides via C=0 O bond cleavage

被引：0
|
作者：
Chen, Lan [1 ]
Zhou, Wei [1 ]
Zhang, Jianwen [1 ]
Ding, Yimin [1 ]
Szostak, Michal [2 ]
Liu, Chengwei [1 ]
机构：
[1] Shanghai Univ, Dept Chem, 99 Shangda Rd, Shanghai 200444, Peoples R China
[2] Rutgers State Univ, Dept Chem, 73 Warren St, Newark, NJ 07102 USA
来源：
CHEMICAL COMMUNICATIONS | 2024年 / 60卷 / 64期
关键词：
C-H ACTIVATION; GRIGNARD; SILYLATION; REDUCTION; REAGENTS; LACTAMS; AMINE; IMINE; 1ST;
D O I：
10.1039/d4cc02316a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A novel deoxygenative alkynylation of amides promoted by a synergistic action of a divalent rare-earth element and a transition metal has been developed. In this method, alpha-alkynyl substituted amines are synthesized from unactivated amides and alkynes in a single transformation. Broad substrate scope and excellent selectivity for C=O cleavage has been demonstrated. This approach represents a general method for the construction of versatile alpha-alkynyl substituted amines from unactivated amide bonds.
引用
收藏
页码：8454 / 8457
页数：4
相关论文
共 50 条
  • [1] Deoxygenative alkynylation of amides via C 00000000 00000000 00000000 00000000 11111111 00000000 11111111 00000000 00000000 00000000 O bond cleavage
    Chen, Lan
    Zhou, Wei
    Zhang, Jianwen
    Ding, Yimin
    Szostak, Michal
    Liu, Chengwei
    Chemical Communications, 2024, 60 (64) : 8454 - 8457
  • [2] Nickel-Catalyzed Alkynylation of Anisoles via C-O Bond Cleavage
    Tobisu, Mamoru
    Takahira, Tsuyoshi
    Ohtsuki, Akimichi
    Chatani, Naoto
    ORGANIC LETTERS, 2015, 17 (03) : 680 - 683
  • [3] Nitrogenation of Amides via C-C and C-N Bond Cleavage
    Zhu, Ming -Hui
    Cheng, Zengrui
    Wei, Jialiang
    Tan, Hui
    Jiao, Ning
    CCS CHEMISTRY, 2023, 5 (05): : 1061 - 1068
  • [4] Transamidation via C-N bond cleavage of amides and tertiary amines
    Idris, Muhammad Aliyu
    Lee, Sunwoo
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (18): : 2737 - 2743
  • [5] Carbon-Carbon Bond Formation of Trifluoroacetyl Amides with Grignard Reagents via C(O)-CF3 Bond Cleavage
    Zhu, Longzhi
    Le, Liyuan
    Yang, Mingpan
    Au, Chak-Tong
    Qiu, Renhua
    Kambe, Nobuaki
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (09): : 5635 - 5644
  • [6] Alkynylation of Tertiary Cycloalkanols via Radical C-C Bond Cleavage: A Route to Distal Alkynylated Ketones
    Wang, Shun
    Guo, Li Na
    Wang, Hua
    Duan, Xin-Hua
    ORGANIC LETTERS, 2015, 17 (19) : 4798 - 4801
  • [7] Scalable deoxygenative alkynylation of alcohols via flow photochemistry
    Xu, Pin
    Ma, Cong
    COMMUNICATIONS CHEMISTRY, 2024, 7 (01):
  • [8] Cobalt-Catalyzed Bis-alkynylation of Amides via Double C-H Bond Activation
    Landge, Vinod G.
    Jaiswal, Garima
    Balaraman, Ekambaram
    ORGANIC LETTERS, 2016, 18 (04) : 812 - 815
  • [9] Base-catalyzed synthesis of amides and imines via C-C and C=C bond cleavage
    Yadav, Dilip Kumar T.
    Bhanage, Bhalchandra M.
    RSC ADVANCES, 2015, 5 (16) : 12387 - 12391
  • [10] Palladium-Catalyzed Decarboxylative Alkynylation of α-Acyloxyketones by C(sp3)-O Bond Cleavage
    Doi, Ryohei
    Yabuta, Akimasa
    Sato, Yoshihiro
    CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (23) : 5884 - 5888
12345