Copper-Catalyzed Cross-Coupling of Secondary -Haloamides with Terminal Alkynes: Access to Diverse 2,3-Allenamides

被引:6
|
作者
Lv, Yunhe [1 ,2 ]
Pu, Weiya [1 ]
Zhu, Xueli [1 ]
Zhao, Tiantian [1 ]
Lin, Feifei [1 ]
机构
[1] Anyang Normal Univ, Coll Chem & Chem Engn, Anyang 455000, Peoples R China
[2] Henan Prov Key Lab New Optoelect Funct Mat, Anyang 455000, Peoples R China
关键词
Alkynes; copper; cross-coupling; -haloamides; trisubstituted allenes; ONE-POT SYNTHESIS; PROPARGYLIC ALCOHOLS; EFFICIENT SYNTHESIS; 1,3-DISUBSTITUTED ALLENES; TRISUBSTITUTED ALLENES; ROOM-TEMPERATURE; CHIRAL ALLENES; ENANTIOSELECTIVE SYNTHESIS; SYNTHETIC APPLICATIONS; SONOGASHIRA REACTIONS;
D O I
10.1002/adsc.201701556
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A copper-catalyzed C(sp)-C(sp(3)) cross-coupling of terminal alkynes with readily available secondary -haloamides for the efficient synthesis of 2,3-allenamides is realized. The methodology is characterized by its wide substrate scope, which makes it an important complement to traditional methods for synthesizing allenes. A mechanism involving an alkynylcopper species is proposed.
引用
收藏
页码:1397 / 1401
页数:5
相关论文
共 50 条
  • [41] Microwave-Assisted Copper-Catalyzed Cross-Coupling Reaction of Alkynes with Aryl Iodides and Vinyl Halides
    Tsai, Wen-Ting
    Lin, Yun-Yung
    Wang, Yu-Jen
    Lee, Chin-Fa
    SYNTHESIS-STUTTGART, 2012, 44 (10): : 1507 - 1510
  • [42] Ligand-Free Copper-Catalyzed Cross-Coupling Reaction of Alkynes with Aryl Iodides and Vinyl Halides
    Tsai, Wan-Ting
    Lin, Yun-Yung
    Chen, Yi-An
    Lee, Chin-Fa
    SYNLETT, 2014, 25 (03) : 443 - 447
  • [43] A Copper-Catalyzed Sonogashira Coupling Reaction of Diverse Activated Alkyl Halides with Terminal Alkynes Under Ambient Conditions
    Cao, Yu-Xi
    Dong, Xiao-Yang
    Yang, Jun
    Jiang, Sheng-Peng
    Zhou, Shuangliu
    Li, Zhong-Liang
    Chen, Guo-Qiang
    Liu, Xin-Yuan
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (11) : 2280 - 2284
  • [44] Divergent Palladium-Catalyzed Cross-Coupling of Nitropyrazoles with Terminal Alkynes
    Ha, Hyeri
    Shin, Changhoon
    Bae, Seri
    Joo, Jung Min
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (20-21) : 2645 - 2650
  • [45] Selective Manganese-Catalyzed Dimerization and Cross-Coupling of Terminal Alkynes
    Weber, Stefan
    Veiros, Luis F.
    Kirchner, Karl
    ACS Catalysis, 2021, 11 : 6474 - 6483
  • [46] Selective Manganese-Catalyzed Dimerization and Cross-Coupling of Terminal Alkynes
    Weber, Stefan
    Veiros, Luis F.
    Kirchner, Karl
    ACS CATALYSIS, 2021, 11 (11): : 6474 - 6483
  • [47] Copper-Catalyzed Cross-Coupling of Nonactivated Secondary Alkyl Halides and Tosylates with Secondary Alkyl Grignard Reagents
    Yang, Chu-Ting
    Zhang, Zhen-Qi
    Liang, Jun
    Liu, Jing-Hui
    Lu, Xiao-Yu
    Chen, Huan-Huan
    Liu, Lei
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (27) : 11124 - 11127
  • [48] Copper-Catalyzed Regiodivergent Borylation of Fluorinated Alkynes and Palladium-Catalyzed Regiospecific Suzuki-Miyaura Cross-Coupling
    Rummler, Lenaic
    El Sater, Mariam Abd
    Blanchard, Nicolas
    Bizet, Vincent
    SYNLETT, 2024, 35 (10) : 1107 - 1112
  • [49] Copper-Catalyzed Cross-Coupling of Fluorinated Vinylstannanes with Organic Halides
    Zine, Khalid
    Petrignet, Julien
    Delaye, Pierre-Olivier
    Carcenac, Yvan
    Parrain, Jean-Luc
    Abarbri, Mohamed
    CHEMISTRYSELECT, 2016, 1 (02): : 272 - 276
  • [50] Copper-Catalyzed Enantioselective Reductive Cross-Coupling of Aldehydes and Imines
    Mitsui, Atsuhisa
    Nagao, Kazunori
    Ohmiya, Hirohisa
    ORGANIC LETTERS, 2020, 22 (03) : 800 - 803