Arylation/Intramolecular Conjugate Addition of 1,6-Enynes Enabled by Manganese(I)-Catalyzed C-H Bond Activation

被引：40
作者：
Tan, Yun-Xuan [1 ]
Liu, Xing-Yu [1 ,2 ]
Zhao, Yi-Shuang [1 ]
Tian, Ping [1 ,3 ]
Lin, Guo-Qiang [1 ,2 ,3 ]
机构：
[1] Univ Chinese Acad Sci, Shanghai Inst Organ Chem, CAS Key Lab Synthet Chem Nat Subst, 345 Lingling Rd, Shanghai 200032, Peoples R China
[2] ShanghaiTech Univ, Sch Phys Sci & Technol, 100 Haike Rd, Shanghai 201210, Peoples R China
[3] Shanghai Univ Tradit Chinese Med, Innovat Res Inst Tradit Chinese Med IRI, 1200 Cailun Rd, Shanghai 201203, Peoples R China
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 01期
关键词：
MANGANESE-CATALYZED SYNTHESIS; ARYLATIVE CYCLIZATION; COBALT CATALYSIS; CARBENE ANIONS; ALKYNES; ACCESS; FUNCTIONALIZATION; MECHANISM; ALLENES; ESTERS;
D O I：
10.1021/acs.orglett.8b03288
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An arylation/intramolecular conjugate addition of cyclohexadienone-containing 1,6-enynes has been established through initiation by manganese(I)-catalyzed C-H bond activation. This tandem reaction involved unusual E/Z-isomerized alkenyl-Mn intermediates and proceeded smoothly with high chemoselectivities and perfect atom economy. The cyclization products could be further transformed to various structures. Mechanistic studies suggested that cleavage of the C-H bond was involved in the turnover-limiting step, and a manganese carbene anion intermediate was proposed to explain such an E/Z isomerization process.
引用
收藏
页码：5 / 9
页数：5
相关论文
共 78 条
  • [1] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope
    Ackermann, Lutz
    [J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1315 - 1345
  • [2] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage
    Ackermann, Lutz
    Vicente, Ruben
    Kapdi, Anant R.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) : 9792 - 9826
  • [3] Total Synthesis of Incarviditone and Incarvilleatone
    Brown, Patrick D.
    Willis, Anthony C.
    Sherburn, Michael S.
    Lawrence, Andrew L.
    [J]. ORGANIC LETTERS, 2012, 14 (17) : 4537 - 4539
  • [4] Manganese-catalyzed synthesis of monofluoroalkenes via C-H activation and C-F cleavage
    Cai, Sai-Hu
    Ye, Lu
    Wang, Ding-Xing
    Wang, Yi-Qiu
    Lai, Lin-Jie
    Zhu, Chuan
    Feng, Chao
    Loh, Teck-Peng
    [J]. CHEMICAL COMMUNICATIONS, 2017, 53 (62) : 8731 - 8734
  • [5] Manganese(I)-Catalyzed Direct C-H Allylation of Arenes with Allenes
    Chen, Shi-Yong
    Li, Qingjiang
    Wang, Honggen
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (20) : 11173 - 11181
  • [6] Manganese(I)-Catalyzed Regio- and Stereoselective 1,2-Diheteroarylation of Allenes: Combination of C-H Activation and Smiles Rearrangement
    Chen, Shi-Yong
    Han, Xiang-Lei
    Wu, Jia-Qiang
    Li, Qingjiang
    Chen, Yunyun
    Wang, Honggen
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (33) : 9939 - 9943
  • [7] Polycyclization Enabled by Relay Catalysis: One-Pot Manganese-Catalyzed C-H Allylation and Silver-Catalyzed Povarov Reaction
    Chen, Shi-Yong
    Li, Qingjiang
    Liu, Xu-Ge
    Wu, Jia-Qiang
    Zhang, Shang-Shi
    Wang, Honggen
    [J]. CHEMSUSCHEM, 2017, 10 (11) : 2360 - 2364
  • [8] Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality
    Chen, Xiao
    Engle, Keary M.
    Wang, Dong-Hui
    Yu, Jin-Quan
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) : 5094 - 5115
  • [9] Z-Selective Olefin Synthesis via Iron-Catalyzed Reductive Coupling of Alkyl Halides with Terminal Arylalkynes
    Cheung, Chi Wai
    Zhurkin, Fedor E.
    Hu, Xile
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (15) : 4932 - 4935
  • [10] Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation
    Cho, Seung Hwan
    Kim, Ji Young
    Kwak, Jaesung
    Chang, Sukbok
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 5068 - 5083
12345678