Copper-catalyzed vinylation of hydrazides. A regioselective entry to highly substituted pyrroles

被引：105
|
作者：
Rivero, Marta Rodriguez [1 ]
Buchwald, Stephen L. [1 ]
机构：
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
来源：
ORGANIC LETTERS | 2007年 / 9卷 / 06期
关键词：
D O I：
10.1021/ol062978s
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A modular route to highly substituted pyrroles has been developed. This transformation consists of two sequential copper-catalyzed vinylations of bis-Boc-hydrazine followed by thermal rearrangement/cyclization. A wide variety of functionalized pyrroles can be prepared in a selective manner from simple and easily accessible precursors.
引用
收藏
页码：973 / 976
页数：4
相关论文
共 50 条
  • [21] Highly Diastereoselective and Regioselective Copper-Catalyzed Nitrosoformate Dearomatization Reaction under AerobicOxidation Conditions
    Yang, Weibo
    Huang, Long
    Yu, Yang
    Pflaesterer, Daniel
    Rominger, Frank
    Hashmi, A. Stephen K.
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (14) : 3927 - 3931
  • [22] Synthesis of N-aryl hydrazides by copper-catalyzed coupling of hydrazides with aryl iodides
    Wolter, M
    Klapars, A
    Buchwald, SL
    ORGANIC LETTERS, 2001, 3 (23) : 3803 - 3805
  • [23] Copper-catalyzed highly regioselective 2-aryloxylation of 2,x-dihalopyridines
    Zhou, Qizhong
    Zhang, Bin
    Du, Tieqi
    Gu, Haining
    Ye, Yuyuan
    Jiang, Huajiang
    Chen, Rener
    TETRAHEDRON, 2013, 69 (01) : 327 - 333
  • [24] Highly Regioselective Copper-Catalyzed Benzylic C?H Amination by N-Fluorobenzenesulfonimide
    Ni, Zhikun
    Zhang, Qian
    Xiong, Tao
    Zheng, Yiying
    Li, Yan
    Zhang, Hongwei
    Zhang, Jingping
    Liu, Qun
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (05) : 1244 - 1247
  • [25] Highly regioselective radical alkylation of 3-substituted pyrroles
    Guadarrama-Morales, Oscar
    Mendez, Francisco
    Miranda, Luis D.
    TETRAHEDRON LETTERS, 2007, 48 (26) : 4515 - 4518
  • [26] Copper-Catalyzed Alkynylation of Hydrazides: An Easy Access to Functionalized Azadipeptides
    Le Du, Eliott
    Borrel, Julien
    Waser, Jerome
    ORGANIC LETTERS, 2022, 24 (36) : 6614 - 6618
  • [27] Efficient Copper-Catalyzed S-Vinylation of Thiols with Vinyl Halides
    Kao, Hsin-Lun
    Lee, Chin-Fa
    ORGANIC LETTERS, 2011, 13 (19) : 5204 - 5207
  • [28] Mild copper-catalyzed vinylation reactions of azoles and Phenols with vinyl bromides
    Taillefer, Marc
    Ouali, Armelle
    Renard, Brice
    Spindler, Jean-Francis
    CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (20) : 5301 - 5313
  • [29] Sequential copper-catalyzed vinylation/cyclization: An efficient synthesis of functionalized oxazoles
    Martin, Rubn
    Cuenca, Ana
    Buchwald, Stephen L.
    ORGANIC LETTERS, 2007, 9 (26) : 5521 - 5524
  • [30] Copper-catalyzed homocoupling of ketoxime carboxylates for synthesis of symmetrical pyrroles
    Ran, Longfei
    Ren, Zhi-Hui
    Wang, Yao-Yu
    Guan, Zheng-Hui
    GREEN CHEMISTRY, 2014, 16 (01) : 112 - 115
12345