Deboronative Selenylation, Bromination, or Hydroxylation of Organic Boronic Acids Facilitated by Tetrabutylammonium Tribromide under Transition Metal-Free Conditions

被引:0
|
作者
Tian Yongsheng [1 ]
Wei Lanfeng [3 ]
Huang Jiawei [1 ]
Wei Yu [1 ]
Xu Liang [1 ]
Liu Shuai [2 ]
机构
[1] Shihezi Univ, Sch Chem & Chem Engn, State Key Lab Incubat Base Green Proc Chem Engine, Shihezi 832003, Xinjiang, Peoples R China
[2] Shihezi Univ, Bintuan Energy Dev Inst, Shihezi 832003, Xinjiang, Peoples R China
[3] Xinjiang Inst Engn, Xinjiang Key Lab Coal Mine Disasters Intelligent, Urumqi 830023, Peoples R China
基金
中国国家自然科学基金;
关键词
tetrabutylammonium tribromide; organic boronic acid; selenylation; bromination; hydroxylation; transition metal-free; ARYLBORONIC ACIDS; PHOTOREDOX CATALYSIS; OXIDATIVE HYDROXYLATION; ARYL; FUNCTIONALIZATION; ARYLATION; SOLVENT; PROTODEBORONATION; DISELENIDES; SELENIDES;
D O I
10.6023/cjoc202312023
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Divergent approaches for the convenient ipso-functionalization of organic boronic acids are presented, capitalizing on tetrabutylammonium tribromide (TBATB) under different, yet transition metal-free conditions. Through these methods, a wide array of organoborons can be efficiently converted into their corresponding selenylated, brominated, or hydroxylated products in moderate to excellent yields. The versatility of this strategy lies in its transition metal-free conditions, simple operation, and step-economic pathways, offering a promising idea for the ipso-functionalization of organoborons
引用
收藏
页码:1987 / 1997
页数:11
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  • [1] Metal-Free Protodeboronation of Electron-Rich Arene Boronic Acids and Its Application to ortho-Functionalization of Electron-Rich Arenes Using a Boronic Acid as a Blocking Group
    Ahn, Su-Jin
    Lee, Chun-Young
    Kim, Nak-Kyoon
    Cheon, Cheol-Hong
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (16): : 7277 - 7285
  • [2] Studies of the boron-carbon linkage Part I The oxidation and nitration of phenylboric acid
    Ainley, AD
    Challenger, F
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1930, : 2171 - 2180
  • [3] Selenium Radical Mediated Cascade Cyclization: Concise Synthesis of Selenated Benzofurans (Benzothiophenes)
    An, Cui
    Li, Chen-Yuan
    Huang, Xiao-Bo
    Gao, Wen-Xia
    Zhou, Yun-Bing
    Liu, Miao-Chang
    Wu, Hua-Yue
    [J]. ORGANIC LETTERS, 2019, 21 (17) : 6710 - 6714
  • [4] Acid-catalyzed oxidative cleavage of S-S and Se-Se bonds with DEAD: efficient access to sulfides and selenides
    An, Rui
    Liao, Lihao
    Liu, Xiang
    Song, Shuqin
    Zhao, Xiaodan
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (24): : 3557 - 3561
  • [5] Mechanism of Cu-Catalyzed Iododeboronation: A Description of Ligand-Enabled Transmetalation, Disproportionation, and Turnover in Cu-Mediated Oxidative Coupling Reactions
    Andrews, Matthew J.
    Carpentier, Ambre
    Slawin, Alexandra M. Z.
    Cordes, David B.
    Macgregor, Stuart A.
    Watson, Allan J. B.
    [J]. ACS CATALYSIS, 2023, 13 (16) : 11117 - 11126
  • [6] Nickel-Catalyzed Intramolecular Decarbonylative Coupling of Aryl Selenol Esters
    Bai, Jin-Hua
    Qi, Xiu-Juan
    Sun, Wei
    Yu, Tian-Yang
    Xu, Peng-Fei
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (08) : 2084 - 2088
  • [7] Enhanced Reactivity for Aromatic Bromination via Halogen Bonding with Lactic Acid Derivatives
    Baker, Sarah I.
    Yaghoubi, Mahshid
    Bidwell, Samantha L.
    Pierce, Savannah L.
    Hratchian, Hrant P.
    Baxter, Ryan D.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (13): : 8492 - 8502
  • [8] 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
    [J]. COORDINATION CHEMISTRY REVIEWS, 2021, 442
  • [9] Synthetic utility of biomimicking vanadium bromoperoxidase and n-tetrabutylammonium tribromide (TBATB) in organic synthesis
    Belal, Md.
    Sarkar, Satavisha
    Subramanian, Ranga
    Khan, Abu T.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (13) : 2562 - 2579
  • [10] Photocatalytic Deoxygenation of Sulfoxides Using Visible Light: Mechanistic Investigations and Synthetic Applications
    Clarke, Aimee K.
    Parkin, Alison
    Taylor, Richard J. K.
    Unsworth, William P.
    Rossi-Ashton, James A.
    [J]. ACS CATALYSIS, 2020, 10 (10) : 5814 - 5820