Metal-Free Electrochemical Hydroboration of Olefins

被引:4
作者
Yuan, Qilin [1 ]
Zhang, Xiao [1 ]
Guo, Lin [1 ]
Yang, Chao [1 ]
Xia, Wujiong [1 ,2 ]
机构
[1] Harbin Inst Technol Shenzhen, Sch Sci, State Key Lab Urban Water Resource & Environm, Shenzhen 518055, Peoples R China
[2] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China
关键词
Electrochemical Synthesis; Alkene Hydroboration; Organoboron Derivatives; Anodic Oxidation; ADDITION-REACTIONS; ORGANIC ELECTROSYNTHESIS; BORYL RADICALS; SECONDARY; ALKENES; LIGHT; BOND; ELECTROOXIDATION; METHODOLOGY; ELECTRICITY;
D O I
10.1002/adsc.202300286
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Herein, we reported the electrochemical hydroboration of olefins to access the organoboron derivatives in a one-pot reaction under air and at room temperature. This reaction manifold was applied to a broad range of alkenes with 40-90% yields and good functional group tolerance without using a metal catalyst or an additional hydride source. Mechanistic studies suggested that this anodic oxidation conducted in an undivided cell allowing the production of a boron radical species, which initiates the hydroboration of olefins event by a radical addition process.
引用
收藏
页码:1788 / 1793
页数:6
相关论文
共 86 条
[1]   Addition reactions of bis(pinacolato)diborane(4) to carbonyl enones and synthesis of (pinacolato)2BCH2B and (pinacolato)2BCH2CH2B by insertion and coupling [J].
Abu Ali, H ;
Goldberg, I ;
Srebnik, M .
ORGANOMETALLICS, 2001, 20 (18) :3962-3965
[2]   Electrochemical Borylation of Electron-Deficient Alkenes and Allenoates [J].
Aelterman, Maude ;
Jubault, Philippe ;
Poisson, Thomas .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (17)
[3]   Electrochemical Hydroboration of Alkynes [J].
Aelterman, Maude ;
Sayes, Morgane ;
Jubault, Philippe ;
Poisson, Thomas .
CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (32) :8277-8282
[4]   Electrochemical instability of highly fluorinated tetraphenyl borates and syntheses of their respective biphenyls [J].
Beil, Sebastian B. ;
Moehle, Sabine ;
Enders, Patrick ;
Waldvogel, Siegfried R. .
CHEMICAL COMMUNICATIONS, 2018, 54 (48) :6128-6131
[5]   Platinum catalysed 3,4- and 1,4-diboration of α,β-unsaturated carbonyl compounds using bis-pinacolatodiboron [J].
Bell, NJ ;
Cox, AJ ;
Cameron, NR ;
Evans, JSO ;
Marder, TB ;
Duin, MA ;
Elsevier, CJ ;
Baucherel, X ;
Tulloch, AAD ;
Tooze, RP .
CHEMICAL COMMUNICATIONS, 2004, (16) :1854-1855
[6]   Organocatalytic versus Iron-Assisted β-Boration of Electron-Deficient Olefins [J].
Bonet, Amadeu ;
Sole, Cristina ;
Gulyas, Henrik ;
Fernandez, Elena .
CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (04) :1011-1014
[7]   First-Row d-Block Element-Catalyzed Carbon-Boron Bond Formation and Related Processes [J].
Bose, Shubhankar Kumar ;
Mao, Lujia ;
Kuehn, Laura ;
Radius, Udo ;
Nekvinda, Jan ;
Santos, Webster L. ;
Westcott, Stephen A. ;
Steel, Patrick G. ;
Marder, Todd B. .
CHEMICAL REVIEWS, 2021, 121 (21) :13238-13341
[8]   Synthesis and Applications of Boronic Acid-Containing Polymers: From Materials to Medicine [J].
Brooks, William L. A. ;
Sumerlin, Brent S. .
CHEMICAL REVIEWS, 2016, 116 (03) :1375-1397
[9]   TRANSITION-METAL-PROMOTED HYDROBORATIONS OF ALKENES, EMERGING METHODOLOGY FOR ORGANIC TRANSFORMATIONS [J].
BURGESS, K ;
OHLMEYER, MJ .
CHEMICAL REVIEWS, 1991, 91 (06) :1179-1191
[10]   Alkenyl Boronates: Synthesis and Applications [J].
Carreras, Javier ;
Caballero, Ana ;
Perez, Pedro J. .
CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (03) :329-343