Myoglobin-catalyzed intermolecular carbene N-H insertion with arylamine substrates

被引：145
|
作者：
Sreenilayam, Gopeekrishnan [1 ]
Fasan, Rudi [1 ]
机构：
[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA
来源：
CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 08期
关键词：
HIGHLY ENANTIOSELECTIVE INSERTION; ALPHA-AMINO-ACIDS; DIAZO-COMPOUNDS; OLEFIN CYCLOPROPANATION; O-H; BONDS; COMPLEXES; ESTERS; ROUTE; DERIVATIVES;
D O I：
10.1039/c4cc08753d
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Engineered variants of the heme-containing protein myoglobin can efficiently catalyze the insertion of alpha-diazo esters into the N-H bond of arylamines, featuring a combination of high chemoselectivity, elevated turnover numbers, and broad substrate scope.
引用
收藏
页码：1532 / 1534
页数：3
相关论文
共 50 条
  • [31] Copper-Catalyzed N-H Insertion and Oxidative Aromatization Cascade: Facile Synthesis of 2-Arylaminophenols
    Ding, Dong
    Lv, Xiaobing
    Li, Jian
    Xu, Guangyang
    Ma, Bing
    Sun, Jiangtao
    CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (06) : 1539 - 1542
  • [32] Palladium catalyzed N-H bond insertion and intramolecular cyclization cascade: the divergent synthesis of heterocyclics
    Ding, Dong
    Liu, Gang
    Xu, Guangyang
    Li, Jian
    Wang, Guoping
    Sun, Jiangtao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (16) : 2533 - 2537
  • [33] Chemoselective carbene insertion into the N-H bonds of NH3•H2O
    Liu, Zhaohong
    Yang, Yong
    Song, Qingmin
    Li, Linxuan
    Zanoni, Giuseppe
    Liu, Shaopeng
    Xiang, Meng
    Anderson, Edward A.
    Bi, Xihe
    NATURE COMMUNICATIONS, 2022, 13 (01)
  • [34] Advances in the Enantioselective Metal-catalyzed N-H and O-H Insertion Reactions with Diazocarbonyl Compounds
    Burtoloso, Antonio C. B.
    Santiago, Joao V.
    Bernardim, Barbara
    Talero, Alexander G.
    CURRENT ORGANIC SYNTHESIS, 2015, 12 (05) : 650 - 659
  • [35] Iridium(III)-Catalyzed Intermolecular C(sp3)-H Insertion Reaction of Quinoid Carbene: A Radical Mechanism
    Wang, Hai-Xu
    Richard, Yann
    Wan, Qingyun
    Zhou, Cong-Ying
    Che, Chi-Ming
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (05) : 1845 - 1850
  • [36] Progress in N-H Insertion Reaction of α-Diazocarbonyl Compounds
    Feng, Jiajun
    Yi, Xiangyan
    Fu, Yaofeng
    Yu, Yang
    Huang, Fei
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (11) : 3013 - 3025
  • [37] Fe-Catalyzed B-H and N-H insertion reactions of iodonium ylides
    An, Hejun
    Cui, Zhi
    Liang, Jinchao
    Ma, Xingxing
    Chen, Jinglong
    Song, Qiuling
    ORGANIC CHEMISTRY FRONTIERS, 2025,
  • [38] Visible-light-induced organocatalytic enantioselective N-H insertion of α-diazoesters enabled by indirect free carbene capture
    Guo, Wengang
    Zhou, Ying
    Xie, Hongling
    Yue, Xin
    Jiang, Feng
    Huang, Hai
    Han, Zhengyu
    Sun, Jianwei
    CHEMICAL SCIENCE, 2023, 14 (04) : 843 - 848
  • [39] Non-aggregated ruthenium naphthalocyanine enabling homogeneous carbene insertion into N-H bonds at low catalyst loading
    Kroitor, Andrey P.
    Martynov, Alexander G.
    Gorbunova, Yulia G.
    Tsivadze, Aslan Yu.
    Sorokin, Alexander B.
    DALTON TRANSACTIONS, 2025, 54 (10) : 4018 - 4024
  • [40] Asymmetric N-H Insertion of Secondary and Primary Anilines under the Catalysis of Palladium and Chiral Guanidine Derivatives
    Zhu, Yin
    Liu, Xiaohua
    Dong, Shunxi
    Zhou, Yuhang
    Li, Wei
    Lin, Lili
    Feng, Xiaoming
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (06) : 1636 - 1640
12345