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
  • [21] Copper-catalyzed cascade coupling/cyclization of terminal alkynes with diazoacetates: a straightforward route for trisubstituted furans
    Zhou, Lei
    Ma, Jiachen
    Zhang, Yan
    Wang, Jianbo
    TETRAHEDRON LETTERS, 2011, 52 (42) : 5484 - 5487
  • [22] Copper-Catalyzed Cross-Coupling of Alkyl and Aryl Grignard Reagents with Alkynyl Halides
    Cahiez, Gerard
    Gager, Olivier
    Buendia, Julien
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (07) : 1278 - 1281
  • [23] Copper-Catalyzed C-N Cross-Coupling of Substituted 2-Halobenzoates with Secondary Acyclic Amides
    Wang, Man-Gang
    Yu, Hua
    Wu, Jun
    Shang, Zhi-Cai
    SYNTHESIS-STUTTGART, 2013, 45 (14): : 1955 - 1964
  • [24] Copper-catalyzed cross-coupling of arenediazonium tetrafluoroborates with polyfluoroarenes
    Zhu, Xingyi
    Li, Feng
    Su, Weike
    TETRAHEDRON LETTERS, 2013, 54 (10) : 1285 - 1289
  • [25] Metal-Catalyzed Cross-Coupling of Terminal Alkynes with Different Carbene Precursors
    Che, Jiuwei
    Xing, Dong
    Hu, Wenhao
    CURRENT ORGANIC CHEMISTRY, 2016, 20 (01) : 41 - 60
  • [26] Copper-catalyzed cross-coupling reactions of nucleobases with arylboronic acids:: An efficient access to N-arylnucleobases
    Yue, Y
    Zheng, ZG
    Wu, B
    Xia, CQ
    Yu, XQ
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (24) : 5154 - 5157
  • [27] Recent Advances in Copper-Catalyzed Carbon Chalcogenides Cross-Coupling Reactions
    Roy, Totan
    Mahata, Atanu
    Kundu, Debasish
    CURRENT ORGANIC SYNTHESIS, 2023, 20 (03) : 267 - 277
  • [28] An Efficient Copper-Catalyzed Cross-Coupling Reaction of Thiols with Aryl Iodides
    Kao, Hsin-Lun
    Chen, Chin-Keng
    Wang, Yu-Jen
    Lee, Chin-Fa
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (09) : 1776 - 1781
  • [29] Copper-Catalyzed Cross-Coupling of Thiols, Alcohols, and Oxygen for the Synthesis of Esters
    Lim, Seungyeon
    Ji, Miran
    Wang, Xi
    Lee, Chan
    Jang, Hye-Young
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (03) : 591 - 595
  • [30] Copper-Catalyzed Thiolation of Terminal Alkynes with N-Thiosuccinimides to Access Alkynyl Sulfides
    Hu, Guo-Qin
    Wang, Cai
    Zhao, Fan
    Liu, Yao-Wei
    Liu, Jing-Hui
    Zhao, Bin
    CHEMISTRYSELECT, 2022, 7 (05):