Copper-Catalyzed Synthesis of N-Aryl and N-Sulfonyl Indoles from 2-Vinylanilines with O2 as Terminal Oxidant and TEMPO as Cocatalyst

被引：25
|
作者：
Liwosz, Timothy W. [1 ]
Chemler, Sherry R. [1 ]
机构：
[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14620 USA
来源：
SYNLETT | 2015年 / 26卷 / 03期
基金：
美国国家卫生研究院;
关键词：
copper; oxidation; indoles; oxygen; TEMPO; C-H ACTIVATION; ONE-POT SYNTHESIS; 4-SUBSTITUTED INDOLES; AEROBIC OXIDATION; PALLADIUM; CYCLIZATION; BOND; ALCOHOLS; ANILINES; HETEROCYCLES;
D O I：
10.1055/s-0034-1379015
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A copper-catalyzed intramolecular alkene oxidative amination that utilizes TEMPO as cocatalyst and O-2 as the terminal oxidant has been developed. The method furnishes N-aryl and N-sulfonyl indoles from N-aryl and N-sulfonyl 2-vinylanilines, respectively. Additionally, sequential copper-catalyzed reactions where initial Chan-Lam coupling of 2-vinylanilines with arylboronic acids is followed by oxidative amination of the alkene can generate N-aryl indoles in one pot.
引用
收藏
页码：335 / 339
页数：5
相关论文
共 50 条
  • [41] Interception of amide ylides with sulfonamides: synthesis of (E)-N-sulfonyl amidines catalyzed by Zn(OTf)2
    Chen, Jijun
    Long, Wenhao
    Fang, Shangwen
    Yang, Yonggang
    Wan, Xiaobing
    CHEMICAL COMMUNICATIONS, 2017, 53 (99) : 13256 - 13259
  • [42] Synthesis of Fluorenes via Tandem Copper-Catalyzed [3+2] Cycloaddition and Rhodium-Catalyzed Denitrogenative Cyclization in a 5-Exo Mode from 2-Ethynylbiaryls and N-Sulfonyl Azides in One Pot
    Seo, Boram
    Jeon, Woo Hyung
    Kim, Jaeeun
    Kim, Sunghwa
    Lee, Phil Ho
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (02): : 722 - 732
  • [43] Regioselective copper-catalyzed amination of chlorobenzoic acids:: Synthesis and solid-state structures of N-aryl anthranilic acid derivatives
    Mei, XF
    August, AT
    Wolf, C
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01): : 142 - 149
  • [44] Synthesis of 3-Aryl-2-(trifluoromethyl)indoles via Copper-Catalyzed Hydroarylation and Subsequent Cadogan Cyclization
    Yamamoto, Yoshishiko
    Ohkubo, Erina
    Shibuya, Masatoshi
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (10) : 1747 - 1751
  • [45] Copper(I) catalysis: Synthesis of N,N′-diarylated and N-aryl,N′-formylated chiral C2-symmetric diamines
    Alakonda, Laxhmaiah
    Periasamy, Mariappan
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (24) : 3859 - 3863
  • [46] Synthesis of Pyrroles from Terminal Alkynes, N-Sulfonyl Azides, and Alkenyl Alkyl Ethers through 1-Sulfonyl-1,2,3-triazoles
    Kim, Cheol-Eui
    Park, Sangjune
    Eom, Dahan
    Seo, Boram
    Lee, Phil Ho
    ORGANIC LETTERS, 2014, 16 (07) : 1900 - 1903
  • [47] Copper-Catalyzed Synthesis of 2-Unsubstituted, N-Substituted Benzimidazoles
    Hirano, Keiichi
    Biju, Akkattu T.
    Glorius, Frank
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (24): : 9570 - 9572
  • [48] PHOTOCHEMICAL SYNTHESIS OF 2,3-DIHYDROINDOLES FROM N-ARYL ENAMINES
    CHAPMAN, OL
    EIAN, GL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (19) : 5329 - &
  • [49] Copper-Catalyzed Oxidative Decarboxylative Arylation of Benzothiazoles with Phenylacetic Acids and α-Hydroxyphenylacetic Acids with O2 as the Sole Oxidant
    Song, Qiuling
    Feng, Qiang
    Zhou, Mingxin
    ORGANIC LETTERS, 2013, 15 (23) : 5990 - 5993
  • [50] Rh(III)-catalyzed synthesis of (dihydro)quinolines via the annulation of N-sulfonyl 2-aminobenzaldehydes with olefins
    Zhang, Yimeng
    Zhang, Tao
    Zhan, Haoqiang
    Li, Xingwei
    CHINESE JOURNAL OF CATALYSIS, 2014, 35 (11) : 1840 - 1845
12345