Electrochemically promoted decarboxylative borylation of alkyl N-hydroxyphthalimide esters

被引：27
|
作者：
Dai, Jian-Jun [1 ,2 ]
Teng, Xin-Xin [1 ]
Fang, Wen [1 ]
Xu, Jun [1 ,2 ]
Xu, Hua-Jian [1 ,2 ]
机构：
[1] Hefei Univ Technol, Sch Food & Biol Engn, Hefei 230009, Peoples R China
[2] Hefei Univ Technol, Anhui Prov Key Lab Adv Catalyt Mat & React Engn, Hefei 230009, Peoples R China
来源：
CHINESE CHEMICAL LETTERS | 2022年 / 33卷 / 03期
基金：
国家重点研发计划; 中国国家自然科学基金;
关键词：
Electrochemical; Decarboxylation; Borylation; Alkyl boronic esters; Redox active esters; IRON-CATALYZED BORYLATION; ORGANIC ELECTROSYNTHESIS; ALKYLBORONIC ESTERS; RADICAL BORYLATION; COUPLING REACTIONS; HALIDES; SECONDARY; HYDROBORATIONS; METHODOLOGY; REAGENTS;
D O I：
10.1016/j.cclet.2021.09.011
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An electrochemically promoted decarboxylative borylation reaction is reported. The reaction proceeds under mild conditions in an undivided cell without use of transition metal- or photo-catalysts. The key feature of the reaction is the compatibility of diboron reagents with the electrochemical conditions. This reaction exhibits broad substrate scope, good functional group tolerability, and easy scalability. (C) 2021 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
引用
收藏
页码：1555 / 1558
页数：4
相关论文
共 50 条
  • [21] Visible-Light-Promoted Reaction of N-Hydroxyphthalimide Esters with Vinyl Boronic Pinacol Ester
    Gkizis, Petros L.
    Triandafillidi, Ierasia
    Stini, Naya A.
    Batsika, Charikleia S.
    Kokotos, Christoforos G.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (15)
  • [22] Selective Syntheses of Z-Alkenes via Photocatalyzed Decarboxylative Coupling of N-Hydroxyphthalimide Esters with Terminal Arylalkynes
    Dai, Guo-Li
    Lai, Shu-Zhen
    Luo, Zhuangzhu
    Tang, Zhen-Yu
    ORGANIC LETTERS, 2019, 21 (07) : 2269 - 2272
  • [23] The Acylation of α-Carbonyl Sulfoxonium Ylides with N-Hydroxyphthalimide Esters
    Mizobuchi, Eduardo F.
    Burtoloso, Antonio C. B.
    SYNTHESIS-STUTTGART, 2025, 57 (05): : 965 - 972
  • [24] Visible-light-induced decarboxylative cascade cyclization of acryloylbenzamides with N-hydroxyphthalimide esters via EDA complexes
    Li, Qing
    Zhu, Zhi-Qiang
    Zhang, Wen-Yi
    Le, Zhang-Gao
    Xie, Zong-Bo
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (05) : 965 - 969
  • [25] Ferric nitrate-promoted oxidative esterification of toluene with N-hydroxyphthalimide: Synthesis of N-hydroxyimide esters
    Li, Pingping
    Sun, Jian
    Xu, Xiaohe
    Mi, Zhisheng
    Lin, Yuyan
    Cheng, Jingya
    Bai, Renren
    Xie, Yuanyuan
    TETRAHEDRON LETTERS, 2018, 59 (27) : 2640 - 2643
  • [26] N-HYDROXYPHTHALIMIDE
    MIAO, FM
    WANG, JL
    MIAO, XS
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1995, 51 : 712 - 713
  • [27] N-hydroxyphthalimide
    Miao, F.-M.
    Wang, J.-L.
    Miao, X.-S.
    Acta Crystallographica, Section C: Crystal Structure Communications, 1995, 51 (pt 4):
  • [28] Advances of N-Hydroxyphthalimide Esters in Photocatalytic Alkylation Reactions
    He Shuaiqi
    Li Haocong
    Chen Xiaolan
    Krylov, Igor B.
    Terent'ev, Alexander O.
    Qu Lingbo
    Yu Bing
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (12) : 4661 - 4689
  • [29] Mechanisms for radical reactions initiating from N-hydroxyphthalimide esters
    Azpilcueta-Nicolas, Carlos R.
    Lumb, Jean-Philip
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2024, 20 : 346 - 378
  • [30] Switchable Decarboxylative Heck-Type Reaction and Oxo-alkylation of Styrenes with N-Hydroxyphthalimide Esters under Photocatalysis
    Xia, Zi-Hao
    Zhang, Chun-Lin
    Gao, Zhong-Hua
    Ye, Song
    ORGANIC LETTERS, 2018, 20 (12) : 3496 - 3499
12345