An efficient and mild iron-mediated synthesis of alkenyl halides via direct C-C bond formation of benzyl alcohols and aryl alkynes

被引：37
|
作者：
Liu, Zhong-Quan [1 ]
Wang, Jianguo
Han, Jie
Zhao, Yankai
Zhou, Bo
机构：
[1] Gannan Normal Univ, Inst Organ Chem, Ganzhou 341000, Jiangxi, Peoples R China
来源：
TETRAHEDRON LETTERS | 2009年 / 50卷 / 11期
关键词：
ALLYLIC ALCOHOLS; CATALYZED BENZYLATION; ALKYLATION; SUBSTITUTION;
D O I：
10.1016/j.tetlet.2009.01.013
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
This work demonstrated an efficient and mild method for preparing various substituted alkenyl halides via direct C-C bond formation of benzyl alcohols and aryl alkynes in CH2Cl2 at 50 degrees*C by using 50 mol % of FeCl3 center dot 6H(2)O or FeBr3. Compared with the systems using excessive boron trihalides and stoichiometric n-BuLi to prepare substituted alkenyl halides, the present procedure would provide an excellent alternative due to the environmentally benign system and atom efficiency. (C) 2009 Elsevier Ltd. All rights reserved
引用
收藏
页码：1240 / 1242
页数：3
相关论文
共 28 条
  • [21] Free-Radical Triggered Ordered Domino Reaction: An Approach to C-C Bond Formation via Selective Functionalization of α-Hydroxyl-(sp3)C-H in Fluorinated Alcohols
    Xu, Zhengbao
    Hang, Zhaojia
    Liu, Zhong-Quan
    ORGANIC LETTERS, 2016, 18 (18) : 4470 - 4473
  • [22] General and Facile Method for exo-Methlyene Synthesis via Regioselective C-C Double-Bond Formation Using a Copper-Amine Catalyst System
    Nishikata, Takashi
    Nakamura, Kimiaki
    Itonaga, Kohei
    Ishikawa, Shingo
    ORGANIC LETTERS, 2014, 16 (21) : 5816 - 5819
  • [23] Synthesis of Phosphoramidates: A Facile Approach Based on the C-N Bond Formation via Ir-Catalyzed Direct C-H Amidation
    Kim, Hyunwoo
    Park, Juhyeon
    Kim, Jeung Gon
    Chang, Sukbok
    ORGANIC LETTERS, 2014, 16 (20) : 5466 - 5469
  • [24] Iron-Catalyzed Cascade Arene-Aldehyde Addition/Cyclizations for the Highly Efficient Synthesis of Xanthenes and Its Analogous: Observation of a C-C Bond Cleavage in Indole-Based Triarylmethanes
    Li, Hongfeng
    Yang, Jingyu
    Liu, Yuanhong
    Li, Yanzhong
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (17) : 6797 - 6801
  • [25] Mild Approach to Nucleoside Analogues via Photoredox/Cu-Catalyzed Decarboxylative C-N Bond Formation. Total Synthesis of Oxetanocin A
    Wang, Ruonan
    Xu, Hao
    Banerjee, Arpan
    Cui, Zhongwen
    Ma, Yuyong
    Whittingham, William G.
    Yang, Peng
    Li, Ang
    ORGANIC LETTERS, 2023, 26 (14) : 2691 - 2696
  • [26] Direct Arylation/Alkylation/Magnesiation of Benzyl Alcohols in the Presence of Grignard Reagents via Ni-, Fe-, or Co-Catalyzed sp3 C-O Bond Activation
    Yu, Da-Gang
    Wang, Xin
    Zhu, Ru-Yi
    Luo, Shuang
    Zhang, Xiao-Bo
    Wang, Bi-Qin
    Wang, Lei
    Shi, Zhang-Jie
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (36) : 14638 - 14641
  • [27] Cu(OAc)2 catalyzed N-benzylation of 3-aminocoumarins with primary aromatic amines and alcohols : A new efficient route to access direct C-N bond via monobenzylation of 3-aminocoumarin derivatives
    Kausar, Nazia
    Das, Asish R.
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2018, 95 (01) : 81 - 89
  • [28] tert-Butyl peroxybenzoate (TBPB)-mediated 2-isocyanobiaryl insertion with 1,4-dioxane: efficient synthesis of 6-alkyl phenanthridines via C(sp3)-H/C(sp2)-H bond functionalization
    Cao, Jia-Jia
    Zhu, Tong-Hao
    Wang, Shun-Yi
    Gu, Zheng-Yang
    Wang, Xiang
    Ji, Shun-Jun
    CHEMICAL COMMUNICATIONS, 2014, 50 (49) : 6439 - 6442
123