Synthesis of Substituted Naphthalenes via a Catalytic Ring-Expansion Rearrangement

被引:53
|
作者
Glass, Adam C. [1 ]
Morris, Benjamin B. [1 ]
Zakharov, Lev N. [1 ]
Liu, Shih-Yuan [1 ]
机构
[1] Univ Oregon, Dept Chem, Eugene, OR 97403 USA
基金
美国国家科学基金会;
关键词
D O I
10.1021/ol8019617
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new methodology for the preparation of substituted naphthalenes starting from readily available indenones, organometal reagents, and trimethylsilyldiazomethane via a catalytic rearrangement process is described. Hindered biaryl naphthalenes, including triortho-substituted biaryls, can be accessed through our method. Our results are consistent with a mechanism involving a benzobenzvalene intermediate.
引用
收藏
页码:4855 / 4857
页数:3
相关论文
共 50 条
  • [31] Highly Stereoselective Construction and Chiral Transfer Ring-expansion of Highly Substituted Cyclopropanes
    Nishii, Yoshinori
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2015, 73 (07) : 701 - 712
  • [32] Cyclic polyglycolides via ring-expansion polymerization with cyclic tin catalysts
    Weidner, Steffen M.
    Meyer, Andreas
    Kricheldorf, Hans R.
    EUROPEAN POLYMER JOURNAL, 2024, 207
  • [33] Ring-Expansion Reactions of the Biomass Derivative Cyrene via Enamine Dihalocyclopropanation
    Puschnig, Johannes
    Greatrex, Ben W.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (09)
  • [34] Synthesizing a Trefoil Knotted Block Copolymer via Ring-Expansion Strategy
    Cao, Peng-Fei
    Rong, Li-Han
    Mangadlao, Joey Dacula
    Advincula, Rigoberto C.
    MACROMOLECULES, 2017, 50 (04) : 1473 - 1481
  • [35] Synthesis of β-Selenylated Cyclopentanones via Photoredox-Catalyzed Selenylation/Ring-Expansion Cascades of Alkenyl Cyclobutanols
    Jung, Hye Im
    Kim, Dae Young
    SYNLETT, 2019, 30 (11) : 1361 - 1365
  • [36] Palladium catalyzed synthesis of highly substituted naphthalenes via direct ring construction from amides with alkynes
    Wu, Junliang
    Cui, Xiuling
    Mi, Xia
    Li, Ying
    Wu, Yangjie
    CHEMICAL COMMUNICATIONS, 2010, 46 (36) : 6771 - 6773
  • [37] ELASTOMER PRODUCED BY RING-EXPANSION POLYMERIZATION
    CALDERON, N
    HINRICHS, RL
    CHEMTECH, 1974, 4 (10) : 627 - 630
  • [38] Ligand-modulated ring-expansion
    Carta, Veronica
    Soto, Miguel A.
    MacLachlan, Mark J.
    CHEMICAL COMMUNICATIONS, 2019, 55 (09) : 1245 - 1248
  • [39] RING-EXPANSION IN AROMATIC NITRENES AND CARBENES
    GLEITER, R
    RETTIG, W
    WENTRUP, C
    HELVETICA CHIMICA ACTA, 1974, 57 (07) : 2111 - 2124
  • [40] CYANOGEN AZIDE RING-EXPANSION REACTION
    MCMURRY, JE
    COPPOLIN.AP
    JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (16): : 2821 - 2827