Lewis Acid Catalyzed Regioselective Hydroheteroarylation of Pentafulvenes

被引：10
|
作者：
Chand, S. Sarath [1 ,2 ]
Gopalan, Greeshma [1 ,2 ]
Santhini, P. V. [1 ,2 ]
Preethanuj, P. [2 ]
John, Jubi [2 ]
Harakat, Dominique [3 ]
Jaroschik, Florian [3 ]
Radhakrishnan, K. V. [1 ,2 ]
机构：
[1] Acad Sci & Innovat Res AcSIR, New Delhi 110001, India
[2] Natl Inst Interdisciplinary Sci & Technol CSIR, Organ Chem Sect, Trivandrum 695019, Kerala, India
[3] Univ Reims, Inst Chim Mol Reims CNRS UMR 7312, F-51687 Reims 2, France
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 05期
关键词：
H BOND ACTIVATION; INTERMOLECULAR HYDROARYLATION; CATIONIC POLYFULVENES; 6+3 CYCLOADDITION; INDOLE SYNTHESIS; FACILE SYNTHESIS; AROMATIC IMINES; METAL-COMPLEXES; DOMINO REACTION; FULVENES;
D O I：
10.1021/acs.orglett.6b00047
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A diverse approach toward the catalytic regioselective nucleophilic addition of nitrogen heterocycles to Lewis acid activated pentafulvenes has been established. The developed protocol introduces pentafulvenes as nonsymmetrical alkenes for the hydroheteroarylation reaction, providing alkylidenecyclopentenylation at the C-3 position of indoles and the C-2 position of pyrrole.
引用
收藏
页码：964 / 967
页数：4
相关论文
共 50 条
  • [31] Lewis Acid-Catalyzed Cyclization of Enaminones with Propargylic Alcohols: Regioselective Synthesis of Multisubstituted 1,2-Dihydropyridines
    Shao, Yushang
    Zhu, Kai
    Qin, Zhengchen
    Li, Ende
    Li, Yanzhong
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (11): : 5731 - 5736
  • [32] Copper-Catalyzed Regioselective Intramolecular Electrophilic Sulfenoamination via Lewis Acid Activation of Disulfides under Aerobic Conditions
    Ni, Yang
    Zuo, Honghua
    Li, Yan
    Wu, Yuzhou
    Zhong, Fangrui
    ORGANIC LETTERS, 2018, 20 (14) : 4350 - 4353
  • [33] TRIBUTYLCHLOROSTANNANE AS LEWIS-ACID IN THE REGIOSELECTIVE REDUCTIVE CLEAVAGE OF KETALS
    SRIKRISHNA, A
    VISWAJANANI, R
    SYNLETT, 1995, (01) : 95 - 96
  • [34] Lewis acid catalyzed Povarov reaction of pentafulvenes and spiro[2,4]-hepta-[4,6]-diene: An efficient access to cyclopentene fused quinolines
    Saranya, Shreyass
    Baiju, Thekke Veettil
    Gopalan, Greeshma
    Radhakrishnan, Kokkuvayil Vasu
    SYNTHETIC COMMUNICATIONS, 2018, 48 (07) : 816 - 829
  • [35] ACID-CATALYZED REGIOSELECTIVE NITRATION OF O-XYLENE TO 4-NITRO-O-XYLENE WITH NITROGEN DIOXIDE: BRONSTED ACID VERSUS LEWIS ACID
    Tang, Bo
    Wei, Songbo
    Peng, Xinhua
    SYNTHETIC COMMUNICATIONS, 2014, 44 (14) : 2057 - 2065
  • [36] Lewis-acid-catalyzed phosphorylation of alcohols
    Wang, Xiao-Hong
    Liu, Xuan
    Xue, Ya-Wen
    Wang, Yan-Bin
    Wei, Xiao-Hong
    Su, Qiong
    RSC ADVANCES, 2024, 14 (06) : 3757 - 3760
  • [37] LEWIS ACID CATALYZED REACTIONS ON MINERAL COAL
    KOLLING, G
    HODEK, W
    MEYER, F
    CHEMIE INGENIEUR TECHNIK, 1971, 43 (03) : 147 - &
  • [38] Lewis Acid Catalyzed Reaction of Triphenylmethanol with Acetylacetone
    Konshin, Valery
    Turmasova, Anna
    Konshina, Dzhamilya
    LETTERS IN ORGANIC CHEMISTRY, 2015, 12 (07) : 511 - 515
  • [39] Lewis Acid Catalyzed Asymmetric Cyanohydrin Synthesis
    North, Michael
    Usanov, Dmitry L.
    Young, Carl
    CHEMICAL REVIEWS, 2008, 108 (12) : 5146 - 5226
  • [40] Lewis acid catalyzed phosphorylation utilizing pyrophosphates
    Sculimbrene, Bianca R.
    Coppola, Kyle A.
    Pedretty, Kyle P.
    Testa, Joseph E.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
12345