Enantioselective Intermolecular Benzylic C-H Amination under Chiral Paddle-Wheel Diruthenium Catalysis

被引：1
|
作者：
Makino, Kotoko [1 ,2 ]
Mori, Kohei [1 ,2 ]
Kiryu, Shoichi [1 ]
Miyazawa, Taku [1 ]
Kumagai, Yuhei [1 ]
Higashida, Kosuke [2 ]
Kojima, Masahiro [1 ]
Yoshino, Tatsuhiko [2 ,3 ]
Matsunaga, Shigeki [1 ,2 ]
机构：
[1] Hokkaido Univ, Fac Pharmaceut Sci, Sapporo 0600812, Japan
[2] Kyoto Univ, Grad Sch Sci, Kyoto 6068502, Japan
[3] Kyoto Univ, Hakubi Ctr Adv Res, Kyoto 6068502, Japan
来源：
ACS CATALYSIS | 2024年 / 15卷 / 01期
基金：
日本学术振兴会;
关键词：
Ruthenium catalysis; Asymmetric catalysis; Nitrene; C-H amination; Chemoselectivity; NITROGEN-ATOM TRANSFER; C(SP(3))-H AMINATION; DIRHODIUM TETRACARBOXYLATES; STEREOSELECTIVE-SYNTHESIS; BISMUTH-RHODIUM; BONDS; RUTHENIUM; AZIRIDINATIONS; FUNCTIONALIZATION; AMIDATION;
D O I：
10.1021/acscatal.4c06504
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
A catalytic asymmetric intermolecular benzylic C-H amination was achieved under paddle-wheel diruthenium catalysis. A chiral diruthenium catalyst incorporating (S)-TPPTTL (tetraphenylphthaloyl-(S)-tert-leucine) ligand exhibited notable enantioselectivity, and aminated products were obtained with up to 99% ee. Unique chemoselectivity of the chiral diruthenium catalyst was also found for allylbenzene and alkyl-naphthalene substrates, demonstrating the complementary synthetic utility of chiral paddle-wheel Ru(II)-Ru(III) catalysts to Rh(II) counterparts.
引用
收藏
页码：523 / 528
页数：6
相关论文
共 50 条
  • [31] Catalytic Intermolecular C(sp3)-H Amination: Selective Functionalization of Tertiary C-H Bonds vs Activated Benzylic C-H Bonds
    Brunard, Erwan
    Boquet, Vincent
    Van Elslande, Elsa
    Saget, Tanguy
    Dauban, Philippe
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (17) : 6407 - 6412
  • [32] Copper catalyzed benzylic C-H amination using simple amination reagents
    Wang, Anqi
    Emmert, Marion
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [33] Metalloradical catalysis for stereoselective C-H amination
    Zhang, Peter X.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
  • [34] Photoelectrochemical asymmetric catalysis enables site- and enantioselective cyanation of benzylic C-H bonds
    Cai, Chen-Yan
    Lai, Xiao-Li
    Wang, Yu
    Hu, Hui-Hui
    Song, Jinshuai
    Yang, Ye
    Wang, Cheng
    Xu, Hai-Chao
    NATURE CATALYSIS, 2022, 5 (10) : 943 - 951
  • [35] Enantioselective Radical Trifluoromethylation of Benzylic C-H Bonds via Cooperative Photoredox and Copper Catalysis
    Xu, Pin
    Fan, Wenzheng
    Chen, Pinhong
    Liu, Guosheng
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (30) : 13468 - 13474
  • [36] Stereo- and Enantioselective Benzylic C-H Alkenylation via Photoredox/Nickel Dual Catalysis
    Cheng, Xiaokai
    Li, Tongtong
    Liu, Yuting
    Lu, Zhan
    ACS CATALYSIS, 2021, 11 (17) : 11059 - 11065
  • [37] Rationalizing the Regioselectivity of Azolation of Benzylic C-H Bonds under Photoredox Catalysis
    Sanosa, Nil
    Montiel-Cervantes, Cesar
    Rubio-Munoz, Miguel
    Sampedro, Diego
    Funes-Ardoiz, Ignacio
    SYNLETT, 2024, 35 (10) : 1149 - 1152
  • [38] Site-Selective Electrochemical Benzylic C-H Amination
    Hou, Zhong-Wei
    Liu, Ding-Jin
    Xiong, Peng
    Lai, Xiao-Li
    Song, Jinshuai
    Xu, Hai-Chao
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (06) : 2943 - 2947
  • [39] Chiral polycyclic benzosultams from photocatalytic diastereo- and enantioselective benzylic C-H functionalization
    Zhang, Shaonan
    Dong, Shicheng
    Cheng, Xiuliang
    Ye, Ziqi
    Lin, Lu
    Zhu, Jun
    Gong, Lei
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (24): : 6853 - 6860
  • [40] Site selective gold(i)-catalysed benzylic C-H amination via an intermolecular hydride transfer to triazolinediones
    Bevernaege, Kevin
    Tzouras, Nikolaos V.
    Poater, Albert
    Cavallo, Luigi
    Nolan, Steven P.
    Nahra, Fady
    Winne, Johan M.
    CHEMICAL SCIENCE, 2023, 14 (36) : 9787 - 9794
12345