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
  • [41] Phthalimide-N-sulfonic acid: a new and efficient organocatalyst for the Biginelli reaction under solvent-free conditions
    Kiyani, Hamzeh
    Ghiasi, Maryam
    RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (09) : 6635 - 6648
  • [42] Phthalimide-N-sulfonic acid: a new and efficient organocatalyst for the Biginelli reaction under solvent-free conditions
    Hamzeh Kiyani
    Maryam Ghiasi
    Research on Chemical Intermediates, 2015, 41 : 6635 - 6648
  • [43] Copper-Catalyzed Cross-Coupling Reaction of Thiols with Aryl Iodides under Ligand-Free Conditions
    Huang, Yu-Ting
    Tsai, Wan-Ting
    Badsara, Satpal Singh
    Chan, Chien-Ching
    Lee, Chin-Fa
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2014, 61 (09) : 967 - 974
  • [44] Cu(OAc)2/pyrimidines-catalyzed cross-coupling reactions of aryl iodides and activated aryl bromides with alkynes under aerobic, solvent-free and palladium-free conditions
    Xie Ye-Xiang
    Deng Chen-Liang
    Pi Shao-Feng
    Li Jin-Heng
    Yin Du-Lin
    CHINESE JOURNAL OF CHEMISTRY, 2006, 24 (10) : 1290 - 1294
  • [45] Selective Silylation of Alcohols, Phenols and Oximes Using N-Chlorosaccharin as an Efficient Catalyst under Mild and Solvent-Free Conditions
    Aghapour, Ghasem
    Moghaddam, Ali Kazemi
    Nadali, Samaneh
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2015, 62 (02) : 197 - 203
  • [46] Iodine catalyzed solvent-free cross-dehydrogenative coupling of arylamines and H-phosphonates for the synthesis of N-arylphosphoramidates under atmospheric conditions
    Dar, Bashir Ahmad
    Dangroo, Nisar A.
    Gupta, Amit
    Wali, Aarti
    Khuroo, Mohammad Akbar
    Vishwakarma, Ram A.
    Singh, Baldev
    TETRAHEDRON LETTERS, 2014, 55 (09) : 1544 - 1548
  • [47] Direct synthesis of xanthenes from benzyl alcohols using choline peroxydisulfate ionic liquid as a reagent under otherwise solvent-free conditions
    Soleimani, Omid
    Hosseinian, Asghar
    JOURNAL OF CHEMICAL RESEARCH, 2018, (06) : 337 - 340
  • [48] Dehydrative Cross-Coupling for C-N Bond Construction under Transition-Metal-Free Conditions
    Xing, Huicong
    Chen, Meijuan
    Zhang, Dong
    Geng, Zhishuai
    Xie, Peizhong
    Loh, Teck-Peng
    ORGANIC LETTERS, 2022, 24 (31) : 5657 - 5662
  • [49] Recyclable Heterogeneous Iron Catalyst for C-N Cross-Coupling under Ligand-Free Conditions
    Swapna, K.
    Kumar, A. Vijay
    Reddy, V. Prakash
    Rao, K. Rama
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (19): : 7514 - 7517
  • [50] Direct cross-coupling of aryl alkynyliodines with arylsulfinic acids leading to alkynyl sulfones under catalyst-free conditions
    Wang, Leilei
    Wei, Wei
    Yang, Daoshan
    Cui, Huanhuan
    Yue, Huilan
    Wang, Hua
    TETRAHEDRON LETTERS, 2017, 58 (51) : 4799 - 4802