Tetrasubstituted 1,3-Enynes by Gold-Catalyzed Direct C(sp2)-H Alkynylation of Acceptor-Substituted Enamines

被引：17
作者：
Han, Chunyu [1 ]
Tian, Xianhai [1 ]
Zhang, Huili [1 ]
Rominger, Frank [1 ]
Hashmi, A. Stephen K. [1 ,2 ]
机构：
[1] Heidelberg Univ, Organ Chem Inst, D-69120 Heidelberg, Germany
[2] King Abdulaziz Univ, Fac Sci, Chem Dept, Jeddah 21589, Saudi Arabia
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 12期
关键词：
C-H ALKYNYLATION; TERMINAL ALKYNES; BENZIODOXOLE REAGENTS; ACCESS; DIMERIZATION; RUTHENIUM; ACIDS; EBX;
D O I：
10.1021/acs.orglett.1c01486
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A gold-catalyzed synthesis of tetrasubstituted 1,3-enynes from hypervalent iodine(III) reagents and activated alkenes is reported. This reaction involves an in situ formed alkynyl Au(III) species and a subsequent direct C(sp(2))-H functionalization of alkenes, offering 26 enynes in 62-92% yield with excellent functional group tolerance.
引用
收藏
页码：4764 / 4768
页数：5
相关论文
共 90 条
  • [1] Cu-Catalyzed Fe-Driven Csp-Csp and Csp-Csp2 Cross-Coupling: An Access to 1,3-Diynes and 1,3-Enynes
    Ahammed, Sabir
    Kundu, Debasish
    Ranu, Brindaban C.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (16) : 7391 - 7398
  • [2] Oxidant-free oxidative gold catalysis: the new paradigm in cross-coupling reactions
    Akram, Manjur O.
    Banerjee, Somsuvra
    Saswade, Sagar S.
    Bedi, Vaibhav
    Patil, Nitin T.
    [J]. CHEMICAL COMMUNICATIONS, 2018, 54 (79) : 11069 - 11083
  • [3] Palladium-Catalyzed Direct ortho-Alkynylation of Aromatic Carboxylic Acid Derivatives
    Ano, Yusuke
    Tobisu, Mamoru
    Chatani, Naoto
    [J]. ORGANIC LETTERS, 2012, 14 (01) : 354 - 357
  • [4] Atom Economy B.M., 1995, ANGEW CHEM INT EDIT, V34, P281
  • [5] Palladium-Catalyzed Regio- and Stereoselective Cross-Addition of Terminal Alkynes to Ynol Ethers and Synthesis of 1,4-Enyn-3-ones
    Babu, Madala Hari
    Dwivedi, Vikas
    Kant, Ruchir
    Reddy, Maddi Sridhar
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (12) : 3783 - 3786
  • [6] Gold and hypervalent iodine(iii): liaisons over a decade for electrophilic functional group transfer reactions
    Banerjee, Somsuvra
    Bhoyare, Vivek W.
    Patil, Nitin T.
    [J]. CHEMICAL COMMUNICATIONS, 2020, 56 (18) : 2677 - 2690
  • [7] Benziodoxole-based hypervalent iodine reagents for atom-transfer reactions
    Brand, Jonathan P.
    Gonzalez, Davinia Fernandez
    Nicolai, Stefano
    Waser, Jerome
    [J]. CHEMICAL COMMUNICATIONS, 2011, 47 (01) : 102 - 115
  • [8] Electrophilic alkynylation: the dark side of acetylene chemistry
    Brand, Jonathan P.
    Waser, Jerome
    [J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (11) : 4165 - 4179
  • [9] Para-Selective Gold-Catalyzed Direct Alkynylation of Anilines
    Brand, Jonathan P.
    Waser, Jerome
    [J]. ORGANIC LETTERS, 2012, 14 (03) : 744 - 747
  • [10] One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines
    Brand, Jonathan P.
    Chevalley, Clara
    Waser, Jerome
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 : 565 - 569
123456789