Transition-metal-free C-S, C-Se, and C-Te Bond Formation from Organoboron Compounds

被引:14
|
作者
Sacramento, Manoela [1 ]
Costa, Gabriel P. [1 ]
Barcellos, Angelita M. [1 ]
Perin, Gelson [1 ]
Lenardao, Eder J. [1 ]
Alves, Diego [1 ]
机构
[1] Univ Fed Pelotas UFPel, CCQFA, Lab Sintese Organ Limpa LASOL, POB 354, BR-96010900 Pelotas, RS, Brazil
来源
CHEMICAL RECORD | 2021年 / 21卷 / 10期
关键词
Alternative sources of energy; Boron reagent; Clean procedures; Chalcogenide; Transition-metal-free; COUPLING REACTIONS; ARYLBORONIC ACIDS; DIARYL SELENIDES; BORON REAGENTS; ELECTROPHILIC CYCLIZATION; ORGANOSELENIUM COMPOUNDS; UNSYMMETRICAL DIARYL; REDOX CYCLE; ONE-POT; ANTIOXIDANT;
D O I
10.1002/tcr.202100021
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The present review describes the successful application of organoboron compounds in transition-metal-free C-S, C-Se, and C-Te bond formations. We presented studies regarding these C-Chalcogen bond formations using organoboron reagents, such as boronic acids, boronic esters, borate anions, and several sources of chalcogen atoms/moieties. Moreover, a broad range of transition-metal-free approaches to synthesize sulfides, selenides, and tellurides were described using conventional heating methods, which are sometimes green since they use green solvents, safe reagents, among others. Furthermore, protocols using alternative energy sources, including ultrasound, microwave irradiation, photocatalysis, and electrolytic processes, were also shown to be suitable. These protocols were applied to prepare a broad scope of functionalized chalcogenides with high molecular diversity. These studies and their proposed mechanisms were also reported herein in addition to the reuse of reaction promoters.
引用
收藏
页码:2855 / 2879
页数:25
相关论文
共 50 条
  • [1] Organoboron compounds as versatile reagents in the transition metal-catalyzed C-S, C-Se and C-Te bond formation
    Barcellos, Angelita M.
    Sacramento, Manoela
    da Costa, Gabriel P.
    Perin, Gelson
    Lenardao, Eder Joao
    Alves, Diego
    COORDINATION CHEMISTRY REVIEWS, 2021, 442
  • [2] Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions
    Beletskaya, Irina P.
    Ananikov, Valentine P.
    CHEMICAL REVIEWS, 2011, 111 (03) : 1596 - 1636
  • [3] Transition-metal-free C-S bond cleavage and transformation of organosulfur compounds
    Yang, Ke
    Li, Qin
    Li, Zhengyi
    Sun, Xiaoqiang
    CHEMICAL COMMUNICATIONS, 2023, 59 (36) : 5343 - 5364
  • [4] Transition-Metal-Free C-S Bond Formation: Synthesis of Polysubstituted Diaryl Sulfides and α-Thioarylcarbonyl Compounds
    Zou, Liang-Hua
    Zhao, Cong
    Li, Ping-Gui
    Wang, Ying
    Li, Jie
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (23): : 12892 - 12898
  • [5] A Comprehensive Review of Magnetic Nanocatalysts for C-S, C-Se Bond Formation
    Ali, Radwan
    Han, Jianlin
    Kazemi, Mosstafa
    Javahershenas, Ramin
    CHEMISTRYOPEN, 2025,
  • [6] Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formations via Cross-Coupling and Atom-Economic Addition Reactions. Achievements and Challenges
    Beletskaya, Irina P.
    Ananikov, Valentine P.
    CHEMICAL REVIEWS, 2022, 122 (21) : 16110 - 16293
  • [7] Transition-Metal-Free Coupling Reaction of Dithiocarbamates with Indoles: C-S Bond Formation
    Halimehjani, Azim Ziyaei
    Shokrgozar, Sahar
    Beier, Petr
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (10): : 5778 - 5783
  • [8] Transition-metal-free synthesis of imidazobenzothiazines via domino C-S/C-N bond formation
    Tu, Xingzhao
    Zhou, Lihong
    Li, Zhijie
    Lei, Ning
    Zeng, Qingle
    MONATSHEFTE FUR CHEMIE, 2014, 145 (12): : 1925 - 1931
  • [9] Transition-metal-free synthesis of imidazobenzothiazines via domino C-S/C-N bond formation
    Xingzhao Tu
    Lihong Zhou
    Zhijie Li
    Ning Lei
    Qingle Zeng
    Monatshefte für Chemie - Chemical Monthly, 2014, 145 : 1925 - 1931
  • [10] C-S and C-Se Bond Formation at Bridging Vinyliminium Ligands in Diiron Complexes
    Marchetti, Fabio
    Zacchini, Stefano
    Zanotti, Valerio
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2013, 2013 (29) : 5145 - 5152