Lewis Acid and Fluoroalcohol Mediated Nucleophilic Addition to the C2 Position of Indoles

被引：41
|
作者：
Morimoto, Naoki [1 ]
Morioku, Kumika [2 ]
Suzuk, Hideyuki [3 ]
Takeuchi, Yasuo [1 ]
Nishina, Yuta [3 ,4 ]
机构：
[1] Okayama Univ, Grad Sch Med Dent & Pharmaceut Sci, Div Pharmaceut Sci, Kita Ku, Okayama 7008530, Japan
[2] Okayama Univ, Fac Engn, Dept Appl Chem & Biotechnol, Kita Ku, Okayama 7008530, Japan
[3] Okayama Univ, Res Core Interdisciplinary Sci, Kita Ku, Okayama 7008530, Japan
[4] Japan Sci & Technol Agcy, Precursory Res Embryon Sci & Technol, 4-1-8 Honcho, Kawaguchi, Saitama 3320012, Japan
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 09期
关键词：
N-ACETYL INDOLES; HETEROCYCLIC CHEMISTRY; AROMATIC HETEROCYCLES; BUILDING-BLOCKS; DERIVATIVES; BENZOFUROINDOLINES; FUNCTIONALIZATION; STEREOCHEMISTRY; HYDROARYLATION; CONSTRUCTION;
D O I：
10.1021/acs.orglett.6b00629
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Indole readily undergoes nucleophilic substitution at the C3 site, and many indole derivatives have been functionalized using this property. Indole also forms indolium, which allows electrophilic addition in acidic conditions, but current examples have been limited to intramolecular reactions. C2 site-selective nucleophilic addition to indole derivatives using fluoroalcohol and a Lewis acid was developed.
引用
收藏
页码：2020 / 2023
页数：4
相关论文
共 50 条
  • [21] Lewis acid mediated addition of silyl ketene acetals to sulfinimines
    Kawecki, R
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (23): : 8724 - 8727
  • [22] Zinc triflate as Lewis acid in nucleophilic addition to cyclic N-acyliminium ions
    Pilli, RA
    Robello, LG
    SYNLETT, 2005, (15) : 2297 - 2300
  • [23] Lewis acid catalyzed C-3 alkylidenecyclopentenylation of indoles: an easy access to functionalized indoles and bisindoles
    Chand, S. Sarath
    Sasidhar, B. S.
    Prakash, Praveen
    Sasikumar, P.
    Preethanuj, P.
    Jaroschik, Florian
    Harakat, Dominique
    Vasse, Jean-Luc
    Radhakrishnan, K. V.
    RSC ADVANCES, 2015, 5 (48): : 38075 - 38084
  • [24] A New Methodology for Functionalization at the 3-Position of Indoles by a Combination of Boron Lewis Acid with Nitriles
    Mizoi, Kenta
    Mashima, Yu
    Kawashima, Yuya
    Takahashi, Masato
    Mimori, Seisuke
    Hosokawa, Masakiyo
    Murakami, Yasuoki
    Hamana, Hiroshi
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2015, 63 (07) : 538 - 545
  • [25] C2 oxygenates by chloromethane addition to syngas
    Soong, Y.
    Blackwell, A.G.
    Schehl, R.R.
    Noceti, R.P.
    Fuel Science and Technology International, 1993, 11 (07): : 937 - 950
  • [26] Visible-Light-Mediated Ir(III)-Catalyzed Concomitant C3 Oxidation and C2 Amination of Indoles
    Shukla, Gaurav
    Alam, Tipu
    Srivastava, Hemant Kumar
    Kumar, Ritush
    Patel, Bhisma K.
    ORGANIC LETTERS, 2019, 21 (10) : 3543 - 3547
  • [27] Lewis Acid Mediated Addition of Tri-n-Butylstannylmethylisoxazole with Aldehydes
    Yamamoto, M.
    Ohtsuka, K.
    Kishikawa, K.
    Kohmoto, S.
    Synthetic Communications, 26 (11):
  • [28] Recent Advances in the C2 and C3 Regioselective Direct Arylation of Indoles
    Lebrasseur, Nathalie
    Larrosa, Igor
    ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 105, 2012, 105 : 309 - 351
  • [29] Selective C2 and C3 phosphorylmethylation of indoles with a phosphorylmethyl dibenzothiophenium reagent
    Shi, Xiaomin
    Qu, Hongmei
    Wu, Yaxing
    Wang, Fei
    Chen, Chao
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (15): : 4176 - 4181
  • [30] Lewis acid mediated Michael addition of non-aromatic multiple C-C bonds to α,β-unsaturated dicarbonyl compounds
    Denisov, Dmitry A.
    Novikov, Roman A.
    Tomilov, Yury, V
    TETRAHEDRON LETTERS, 2021, 80
12345