N-Iodosuccinimide as a Precatalyst for Direct Cross-Coupling of Alcohols withC-Nucleophiles under Solvent-Free Reaction Conditions

被引:5
|
作者
Ajvazi, Njomza [1 ]
Stavber, Stojan [1 ,2 ]
机构
[1] Jozef Stefan Int Postgrad Sch, Jamova 39, Ljubljana 1000, Slovenia
[2] Jozef Stefan Inst, Jamova 39, Ljubljana 1000, Slovenia
关键词
alcohols; N-iodosuccinimide; C-C coupling; solvent-free reactions; green chemistry; SUBSTITUTION; ALKYLATION;
D O I
10.3390/catal10080850
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
C-C bond formation is one of the most important implements in synthetic organic chemistry. In pursuit of effective synthetic routes functioning under greener pathways to achieve direct C-C bond formation, we reportN-iodosuccinimide (NIS) as the most effective precatalyst among theN-halosuccinimides (NXSs) for the direct cross-coupling of benzyl alcohols with C-nucleophiles under solvent-free reaction conditions (SFRC). The protocol is metal-free, and air- and water-tolerant, providing a large-scale synthesis with almost quantitative yields.
引用
收藏
页数:8
相关论文
共 50 条
  • [21] Solvent-free N-iodosuccinimide-promoted synthesis of spiroimidazolines from alkenes and amidines under ball-milling conditions
    Xu, Hui
    Chen, Kuan
    Liu, Hong-Wei
    Wang, Guan-Wu
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (19): : 2864 - 2869
  • [22] Ru(II)-NHC catalysed N-Alkylation of amines with alcohols under solvent-free conditions
    Karaca, Emine Ozge
    Dehimat, Zieneb Imene
    Yasar, Sedat
    Gurbuz, Nevin
    Tebbani, Dahmane
    Cetinkaya, Bekir
    Ozdemir, Ismail
    INORGANICA CHIMICA ACTA, 2021, 520
  • [23] Direct substitution of the hydroxy group of alcohols with N-nucleophiles mediated by the substoichiometric amount of SelectfluorTM F-TEDA-BF4 as a precatalyst under mild reaction conditions
    Ajvazi, Njomza
    Stavber, Stojan
    TETRAHEDRON LETTERS, 2023, 115
  • [24] Direct C2-Alkylation of Azoles with Alcohols and Ethers through Dehydrogenative Cross-Coupling under Metal-Free Conditions
    He, Tao
    Yu, Lin
    Zhang, Lei
    Wang, Lei
    Wang, Min
    ORGANIC LETTERS, 2011, 13 (19) : 5016 - 5019
  • [25] Aldol reaction under solvent-free conditions: Highly stereoselective synthesis of 1,3-amino alcohols
    Loh, TP
    Huang, JM
    Goh, SH
    Vittal, JJ
    ORGANIC LETTERS, 2000, 2 (09) : 1291 - 1294
  • [26] FMMWCNTs@CPA@SMTU@PdII NPs: As a Versatile Ferromagnetic Nanostructured Catalyst for Sonogashira-Hagihara Cross-Coupling Reaction in Solvent-Free Conditions
    Ghasemzadeh, Maryam Sadat
    Akhlaghinia, Batool
    CHEMISTRYSELECT, 2019, 4 (04): : 1542 - 1555
  • [27] N-bromosuccinimide (NBS):: a mild and efficient catalyst for tetrahydropyranylation of alcohols and Phenols under solvent-free conditions
    Khazaei, Ardeshir
    Rostami, Amin
    Raiatzadeh, Ayeh
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2007, 54 (04) : 1029 - 1032
  • [28] Synthesis of Quinoxaline Derivatives via Copper(I)-Catalyzed Cross-Coupling Reaction of 1,2-Dihalobenzenes with N,N′-Disubstituted Ethane-1,2-diamines under Ligand- and Solvent-Free Conditions
    Shen, Guodong
    Zhao, Lingyu
    Zhao, Xiliang
    Huangfu, Xinlei
    Li, Zhe
    Wang, Rui
    Zhang, Tongxin
    SYNLETT, 2017, 28 (09) : 1111 - 1115
  • [29] Direct C-4 alkylation of quinazoline N-oxides with ethers via an oxidative cross-coupling reaction under metal-free conditions
    Yang, Qin
    Lou, Minhao
    Yin, Zhijian
    Deng, Zhihong
    Ding, Qiuping
    Peng, Yiyuan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (45) : 8724 - 8731
  • [30] HZSM-5-zeolite as remarkable and reusable catalyst for the direct acetylation of alcohols and phenols under solvent-free conditions
    Heravi, MM
    Tajbakhsh, M
    Mohajerani, B
    Ghassemzadeh, M
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1999, 38 (07): : 859 - 860