Synthesis of Fluorinated Aminoalkylboronic Acids from Amphoteric α-Boryl Aldehydes

被引：6
|
作者：
Soor, Harjeet S. [1 ]
Diaz, Diego B. [1 ]
Burton, Katherine I. [1 ]
Yudin, Andrei K. [1 ]
机构：
[1] Univ Toronto, Dept Chem, 80 St George St, Toronto, ON M5S 3H6, Canada
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2021年 / 60卷 / 30期
基金：
加拿大自然科学与工程研究理事会;
关键词：
aminoalkylboronic acids; electrophilic fluorination; fluorine-containing boronic acids; alpha-boryl aldehydes; STEREOSELECTIVE-SYNTHESIS; NUCLEOPHILIC TRIFLUOROMETHYLATION; BORONIC ACIDS; INHIBITORS; LINCHPINS; BINDING;
D O I：
10.1002/anie.202104133
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Our ongoing search for underdeveloped functional group combinations has brought to light alpha-fluorinated aminoalkylboronic acids, a new class of molecules featuring the B-CF linkage. These compounds can now be generated from secondary amines and alpha-boryl aldehydes through electrophilic fluorination of boryl enamines or enamides. Fluorinated beta-aminoalkylboronic acids show no signs of degradation under ambient conditions. We present evidence for the involvement of chair-like motifs, favored over the acyclic forms by up to 1.7 +/- 0.1 kcal mol(-1) in water and held together by an amine-boronate hydrogen bond. Fluorinated beta-aminoalkylboronic acids are stable over a wide pH range and are characterized by a pK(a) of 3.4, which is the lowest of any alkylboronic acid.
引用
收藏
页码：16366 / 16371
页数：6
相关论文
共 50 条
  • [41] Asymmetric Synthesis of Cyclic Fluorinated Amino Acids
    Hao, Jing
    Milcent, Thierry
    Retailleau, Pascal
    Soloshonok, Vadim A.
    Ongeri, Sandrine
    Crousse, Benoit
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (27-28) : 3688 - 3692
  • [42] Synthesis of new fluorinated derivatives of quinolinecarboxylic acids
    Nosova E.V.
    Sidorova L.P.
    Lipunova G.N.
    Mochul'skaya N.N.
    Chasovskikh O.M.
    Charushin V.N.
    Chemistry of Heterocyclic Compounds, 2002, 38 (08) : 922 - 928
  • [43] Synthesis of new fluorinated derivatives of quinolinecarboxylic acids
    Nosova, EV
    Sidorova, LP
    Lipunova, GN
    Mochul'skaya, NN
    Chasovskikh, OM
    Charushin, VN
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2002, (08): : 1060 - 1066
  • [44] Synthesis of Alkyl Fluorides and Fluorinated Unnatural Amino Acids via Photochemical Decarboxylation of α-Fluorinated Carboxylic Acids
    Gutierrez-Bonet, A'lvaro
    Liu, Wenbin
    ORGANIC LETTERS, 2023, : 483 - 487
  • [45] STRAIGHTFORWARD SYNTHESIS OF 2-ALKENOIC ACIDS FROM THE CORRESPONDING SATURATED ALDEHYDES
    OUTURQUIN, F
    PAULMIER, C
    SYNTHESIS-STUTTGART, 1989, (09): : 690 - 691
  • [46] Synthesis of biarylketones and phthalides from organoboronic acids and aldehydes catalyzed by cobalt complexes
    Karthikeyan, Jaganathan
    Parthasarathy, Kanniyappan
    Cheng, Chien-Hong
    CHEMICAL COMMUNICATIONS, 2011, 47 (37) : 10461 - 10463
  • [47] A one-pot synthesis of tetrahydroisoquinolonic acids from aldehydes and amines in trimethylorthoformate
    Yu, NF
    Poulain, R
    Gesquiere, JC
    SYNLETT, 2000, (03) : 355 - 356
  • [48] THE SYNTHESIS OF BETA-AMINO ACIDS FROM AROMATIC HYDROXY AND ALKOXY ALDEHYDES
    RODIONOV, VM
    DUDINSKAYA, AA
    AVRAMENKO, VG
    SUVOROV, NN
    ZHURNAL OBSHCHEI KHIMII, 1958, 28 (08): : 2242 - 2246
  • [49] Photocatalytic Synthesis of Acetals and Ketals from Aldehydes and Silylenolethers without the Use of Acids
    Steuernagel, Desiree
    Wagenknecht, Hans-Achim
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (13)
  • [50] Synthesis of γ-Oxo γ-Aryl and γ-Aryl α-Amino Acids from Aromatic Aldehydes and Serine
    Chacko, Shibin
    Ramapanicker, Ramesh
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (36) : 7120 - 7128
12345