Lewis Acid Catalyzed Direct Cyanation of Indoles and Pyrroles with N-Cyano-N-phenyl-p-toluenesulfonamide (NCTS)

被引：136
作者：
Yang, Yang
Zhang, Yan
Wang, Jianbo [1 ]
机构：
[1] Peking Univ, Beijing Natl Lab Mol Sci BNLMS, Beijing 100871, Peoples R China
来源：
ORGANIC LETTERS | 2011年 / 13卷 / 20期
关键词：
C-H FUNCTIONALIZATION; ARYL HALIDES; ELECTROPHILIC CYANATION; CONVENIENT PROCEDURE; EFFICIENT SYNTHESIS; AROMATIC NITRILES; REAGENT; BROMIDES; ROUTE; BONDS;
D O I：
10.1021/ol202335p
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
BF3 center dot OEt2-catalyzed direct cyanation of indoles and pyrroles using a less toxic, bench-stable, and easily handled electrophilic cyanating agent N-cyano-N-phenyl-para-toluenesulfonamide (NCTS) affords 3-cyanoindoles and 2-cyanopyrroles in good yields with excellent regioselectivity. The substrate scope is broad with respect to indoles and pyrroles.
引用
收藏
页码：5608 / 5611
页数：4
相关论文
共 63 条
  • [1] A Novel and Convenient Synthesis of Benzonitriles: Electrophilic Cyanation of Aryl and Heteroaryl Bromides
    Anbarasan, Pazhamalai
    Neumann, Helfried
    Beller, Matthias
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (15) : 4217 - 4222
  • [2] A General Rhodium-Catalyzed Cyanation of Aryl and Alkenyl Boronic Acids
    Anbarasan, Pazhamalai
    Neumann, Helfried
    Beller, Matthias
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (02) : 519 - 522
  • [3] A Convenient Synthesis of Benzonitriles via Electrophilic Cyanation with N-Cyanobenzimidazole
    Anbarasan, Pazhamalai
    Neumann, Helfried
    Beller, Matthias
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (16) : 4725 - 4728
  • [4] [Anonymous], 1970, Chemistry of the Cyano Group
  • [5] [Anonymous], 1884, Berichte Dtsch. Chem. Ges, DOI DOI 10.1002/CBER.18840170219
  • [6] Catalytic Functionalization of Indoles in a New Dimension
    Bandini, Marco
    Eichholzer, Astrid
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) : 9608 - 9644
  • [7] INTERACTION OF ARYLTRIMETHYLSTANNANES WITH CYANOGEN CHLORIDE AND BROMIDE - ROUTE TO ARYL CYANIDES
    BARTLETT, EH
    EABORN, C
    WALTON, DRM
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1972, 46 (02) : 267 - 269
  • [8] Gold-mediated C-H bond functionalisation
    Boorman, Tanya C.
    Larrosa, Igor
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (04) : 1910 - 1925
  • [9] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant
    Chen, Xiao
    Hao, Xue-Shi
    Goodhue, Charles E.
    Yu, Jin-Quan
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) : 6790 - 6791
  • [10] A robust palladium-catalyzed cyanation procedure: beneficial effect of zinc acetate
    Chidambaram, R
    [J]. TETRAHEDRON LETTERS, 2004, 45 (07) : 1441 - 1444
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