Boron-Catalyzed O-H Bond Insertion of α-Aryl α-Diazoesters in Water

被引：73
|
作者：
San, Htet Htet [1 ,2 ]
Wang, Shi-Jun [1 ,2 ]
Jiang, Min [3 ]
Tang, Xiang-Ying [1 ,2 ]
机构：
[1] Huazhong Univ Sci & Technol, Sch Chem & Chem Engn, 1037 Luoyu Rd, Wuhan 430074, Hubei, Peoples R China
[2] Huazhong Univ Sci & Technol, Hubei Key Lab Bioinorgan Chem & Mat Med, 1037 Luoyu Rd, Wuhan 430074, Hubei, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 15期
关键词：
FRUSTRATED LEWIS PAIRS; METAL-FREE HYDROGENATION; AROMATIC C-H; B(C6F5)(3)-CATALYZED TRANSFER; SI-H; CARBENOID INSERTION; FACILE PROTOCOL; DIRECT MANNICH; ACID; FUNCTIONALIZATION;
D O I：
10.1021/acs.orglett.8b01988
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A catalytic, metal-free O H bond insertion of alpha-diazoesters in water in the presence of B(C6F5)(3)center dot nH(2)O (2 mol %) was developed, affording a series of alpha-hydroxyesters in good to excellent yields. The reaction features easy operation and wide substrate scope, and importantly, no metal is needed as compared with the conventional methods. Significantly, this approach further expands the applications of B(C6F5)(3) under water-tolerant conditions.
引用
收藏
页码：4672 / 4676
页数：5
相关论文
共 50 条
  • [31] O-H•••C Hydrogen Bond in the Methane-Water Complex
    Isaev, A. N.
    RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY A, 2016, 90 (10) : 1978 - 1985
  • [32] Mechanistic Insight into the Rhodium-Catalyzed O-H Insertion Reaction: A DFT Study
    Xie, Zhi-Zhong
    Liao, Wen-Juan
    Cao, Jun
    Guo, Li-Ping
    Verpoort, Francis
    Fang, Weihai
    ORGANOMETALLICS, 2014, 33 (10) : 2448 - 2456
  • [33] Catalytic enantioselective O-H insertion reactions
    Maier, TC
    Fu, GC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (14) : 4594 - 4595
  • [34] RHODIUM-CARBENOID MEDIATED O-H INSERTION REACTIONS - O-H INSERTION VS H-ABSTRACTION AND EFFECT OF CATALYST
    COX, GG
    MILLER, DJ
    MOODY, CJ
    SIE, ERHB
    KULAGOWSKI, JJ
    TETRAHEDRON, 1994, 50 (10) : 3195 - 3212
  • [35] Catalytic enantioselective O-H insertion reactions
    Maier, Thomas C.
    Fu, Gregory C.
    Journal of the American Chemical Society, 2006, 128 (14): : 4594 - 4595
  • [36] Nickel-Catalyzed Boron Insertion into the C2-O Bond of Benzofurans
    Saito, Hayate
    Otsuka, Shinya
    Nogi, Keisuke
    Yorimitsu, Hideki
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (47) : 15315 - 15318
  • [37] Isolation of an intermediate in the insertion of a carbodiimide into a boron- aryl bond
    Hill, NJ
    Moore, JA
    Findlater, M
    Cowley, AH
    CHEMICAL COMMUNICATIONS, 2005, (43) : 5462 - 5464
  • [38] Group 8 Metals-Catalyzed O-H Bond Addition to Unsaturated Molecules
    Bruneau, Christian
    HYDROFUNCTIONALIZATION, 2013, 43 : 203 - 230
  • [39] THE BOND NUMBER RELATIONSHIP FOR THE O-H ... O SYSTEMS
    GRABOWSKI, SJ
    CROATICA CHEMICA ACTA, 1988, 61 (04) : 815 - 819
  • [40] Catalytic O-H bond insertion reactions using surface modified sewage sludge as a catalyst
    Zhang, Zhipeng
    Yu, Yang
    Huang, Fei
    Yi, Xiangyan
    Xu, Yao
    He, Yide
    Baell, Jonathan B.
    Huang, He
    GREEN CHEMISTRY, 2020, 22 (05) : 1594 - 1604
12345