Acyl Radicals from Aromatic Carboxylic Acids by Means of Visible-Light Photoredox Catalysis

被引：153
作者：
Bergonzini, Giulia [1 ]
Cassani, Carlo [1 ]
Wallentin, Carl-Johan [1 ]
机构：
[1] Gothenburg Univ, Dept Chem & Mol Biol, S-41258 Gothenburg, Sweden
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 47期
基金：
瑞典研究理事会;
关键词：
acyl radicals; acylarylation; carboxylic acids; oxindoles; photoredox catalysis; ALPHA-AMINO-ACIDS; METAL-FREE; MERGING PHOTOREDOX; ROOM-TEMPERATURE; NICKEL CATALYSIS; DECARBOXYLATIVE FLUORINATION; ENANTIOSELECTIVE SYNTHESIS; SYNTHETIC APPLICATIONS; ACTIVATED ALKENES; ACYLATION;
D O I：
10.1002/anie.201506432
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Simple and abundant carboxylic acids have been used as acyl radical precursor by means of visible-light photoredox catalysis. By the transient generation of a reactive anhydride intermediate, this redox-neutral approach offers a mild and rapid entry to high-value heterocyclic compounds without the need of UV irradiation, high temperature, high CO pressure, tin reagents, or peroxides.
引用
收藏
页码：14066 / 14069
页数：4
相关论文
共 66 条
  • [1] [Anonymous], 2015, ANGEW CHEM-GER EDIT
  • [2] Badillo JJ, 2010, CURR OPIN DRUG DISC, V13, P758
  • [3] Strategies for the enantioselective synthesis of spirooxindoles
    Ball-Jones, Nicolas R.
    Badillo, Joseph J.
    Franz, Annaliese K.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (27) : 5165 - 5181
  • [4] A practical access to acyl radicals from acyl hydrazides
    Bath, S
    Laso, NM
    Lopez-Ruiz, H
    Quiclet-Sire, B
    Zard, SZ
    [J]. CHEMICAL COMMUNICATIONS, 2003, (02) : 204 - 205
  • [5] Generation and intramolecular reactivity of acyl radicals from alkynylthiol esters under reducing tin-free conditions
    Benati, L
    Calestani, G
    Leardini, R
    Minozzi, M
    Nanni, D
    Spagnolo, P
    Strazzari, S
    [J]. ORGANIC LETTERS, 2003, 5 (08) : 1313 - 1316
  • [6] Photocatalytic Decarboxylative Reduction of Carboxylic Acids and Its Application in Asymmetric Synthesis
    Cassani, Carlo
    Bergonzini, Giulia
    Wallentin, Carl-Johan
    [J]. ORGANIC LETTERS, 2014, 16 (16) : 4228 - 4231
  • [7] Chemistry of acyl radicals
    Chatgilialoglu, C
    Crich, D
    Komatsu, M
    Ryu, I
    [J]. CHEMICAL REVIEWS, 1999, 99 (08) : 1991 - 2069
  • [8] Redox-economical radical generation from organoborates and carboxylic acids by organic photoredox catalysis
    Chinzei, Tatsuya
    Miyazawa, Kazuki
    Yasu, Yusuke
    Koike, Takashi
    Akita, Munetaka
    [J]. RSC ADVANCES, 2015, 5 (27) : 21297 - 21300
  • [9] Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones by the Decarboxylative Arylation of -Oxo Acids
    Chu, Lingling
    Lipshultz, Jeffrey M.
    MacMillan, David W. C.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (27) : 7929 - 7933
  • [10] Carboxylic Acids as A Traceless Activation Group for Conjugate Additions: A Three-Step Synthesis of (±)-Pregabalin
    Chu, Lingling
    Ohta, Chisa
    Zuo, Zhiwei
    MacMillan, David W. C.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (31) : 10886 - 10889
1234567