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
  • [31] The journey of C-S bond formation from metal catalysis to electrocatalysis
    Chen, Ze-Wei
    Bai, Rekha
    Annamalai, Pratheepkumar
    Badsara, Satpal Singh
    Lee, Chin-Fa
    NEW JOURNAL OF CHEMISTRY, 2021, 46 (01) : 15 - 38
  • [32] A NEW METHOD FOR RADICAL GENERATION - REDUCTIVE C-SE OR C-S BOND-CLEAVAGE OF CYCLIC ONIUM SALTS
    KATAOKA, T
    TSUTSUMI, K
    KANO, K
    MORI, K
    MIYAKE, M
    YOKOTA, M
    SHIMIZU, H
    HORI, M
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11): : 3017 - 3025
  • [33] Construction of C-S and C-Se Bonds from Unstrained Ketone Precursors under Photoredox Catalysis
    Liu Xinyu
    Wang Shunyi
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (04) : 1382 - 1384
  • [34] Construction of C-S and C-Se Bonds from Unstrained Ketone Precursors under Photoredox Catalysis
    Wu, Hao
    Chen, Shuguang
    Liu, Chunni
    Zhao, Quansheng
    Wang, Zhen
    Jin, Qiren
    Sun, Shijie
    Guo, Jing
    He, Xinwei
    Walsh, Patrick J.
    Shang, Yongjia
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (08)
  • [35] C–F bond activation under transition-metal-free conditions
    HanJun Ai
    Xingxing Ma
    Qiuling Song
    XiaoFeng Wu
    Science China(Chemistry), 2021, (10) : 1630 - 1659
  • [36] C–F bond activation under transition-metal-free conditions
    Han-Jun Ai
    Xingxing Ma
    Qiuling Song
    Xiao-Feng Wu
    Science China(Chemistry), 2021, 64 (10) : 1630 - 1659
  • [37] Progress in the Formation of C-S Bond
    Sun, Fengli
    Liu, Xuemin
    Chen, Xinzhi
    Qian, Chao
    Ge, Xin
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (09) : 2211 - 2220
  • [38] A four-component protocol for tandem C-S and C-C bond formation to access thienopyrrolediones under transition-metal free conditions
    Xing, Qiaoyan
    Qu, Hongzhi
    Chen, Ya
    Xiao, Fuhong
    Deng, Guo-Jun
    TETRAHEDRON, 2024, 158
  • [39] Sulfenylation of C-H Bonds for C-S Bond Formation under Metal-Free Conditions
    Dong, Dao-Qing
    Hao, Shuang-Hong
    Yang, Dao-Shan
    Li, Li-Xia
    Wang, Zu-Li
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (45) : 6576 - 6592
  • [40] The effects of C-S and C-Se bonds on torquoselectivity: stereoselective olefination of α-thio and α-selenoketones with ynolates
    Yoshikawa, Takashi
    Mori, Seiji
    Shindo, Mitsuru
    TETRAHEDRON, 2009, 65 (43) : 8832 - 8838