Multicomponent Synthesis of α-Branched Tertiary and Secondary Amines by Photocatalytic Hydrogen Atom Transfer Strategy

被引：35
|
作者：
Qi, Xu-Kuan [1 ]
Guo, Lin [1 ]
Yao, Li-Juan [1 ]
Gao, Han [1 ]
Yang, Chao [1 ]
Xia, Wujiong [1 ,2 ]
机构：
[1] Harbin Inst Technol Shenzhen, Sch Sci, State Key Lab Urban Water Resource & Environm, Shenzhen 518055, Peoples R China
[2] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 11期
基金：
中国国家自然科学基金;
关键词：
REDUCTIVE AMINATION;
D O I：
10.1021/acs.orglett.1c01412
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A multicomponent carbonyl alkylative amination reaction is described. A variety of N-arylamines, aldehydes, and hydrocarbons have been examined as reaction substrates using tetrabutylammonium decatungstate as photocatalyst, providing the corresponding alpha-branched tertiary and secondary amines in good to moderate yields. The reaction proceeds through the generation of alkyl radicals by a light-promoted hydrogen atom transfer process followed by free radical addition to iminium ions generated in situ.
引用
收藏
页码：4473 / 4477
页数：5
相关论文
共 50 条
  • [31] SECONDARY AND TERTIARY STRAIGHT-CHAIN AND BRANCHED-CHAIN AMIDES AND AMINES - NEMATICIDES FOR PANAGRELLUS AND MELOIDOGYNE
    FELDMESSER, J
    THOMPSON, MJ
    ROBBINS, WE
    SPONAUGLE, RP
    JOURNAL OF NEMATOLOGY, 1975, 7 (04) : 321 - 322
  • [32] Facile Multicomponent Synthesis of Oxazolidinones from Primary Amines and Cesium (Hydrogen)Carbonate
    Fehr, Lorenz
    Sewald, Leonard
    Huber, Robert
    Kaiser, Markus
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (27)
  • [33] SYNTHESIS OF BRANCHED DEUTERIUM-LABELLED HYDROCARBONS CONTAINING DEUTERIUM AT TERTIARY CARBON ATOM
    PARNES, ZN
    KHOTIMSK.GA
    LYAKHOVE.YI
    PETROVSK.PV
    IZVESTIYA AKADEMII NAUK SSSR-SERIYA KHIMICHESKAYA, 1971, (07): : 1562 - +
  • [34] Photocatalytic Hydrogen Atom Transfer-Induced Arbuzov-Type α-C(sp3)-H Phosphonylation of Aliphatic Amines
    Lei, Zhexuan
    Zhang, Weigang
    Wu, Jie
    ACS CATALYSIS, 2023, 13 (24) : 16105 - 16113
  • [35] Total Synthesis enabled by Epimerization with Hydrogen Atom Transfer
    Okamura, Toshitaka
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2024, 82 (04) : 377 - 378
  • [36] Cobalt-Catalyzed Synthesis of Aromatic, Aliphatic, and Cyclic Secondary Amines via a "Hydrogen-Borrowing" Strategy
    Yin, Zhiwei
    Zeng, Haisu
    Wu, Jing
    Zheng, Shengping
    Zhang, Guoqi
    ACS CATALYSIS, 2016, 6 (10): : 6546 - 6550
  • [37] Synthesis of nitrogen heterocycles based on atom transfer carbonylation of bifunctional amines
    Kreimerman, S
    Ryu, I
    Minakata, S
    Komatsu, M
    COMPTES RENDUS DE L ACADEMIE DES SCIENCES SERIE II FASCICULE C-CHIMIE, 2001, 4 (06): : 497 - 503
  • [38] Synthesis of Chlorinated Oligopeptides via γ- and δ-Selective Hydrogen Atom Transfer Enabled by the N-Chloropeptide Strategy
    Nanjo, Takeshi
    Matsumoto, Ayaka
    Oshita, Takuma
    Takemoto, Yoshiji
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (34) : 19067 - 19075
  • [39] Atom elimination strategy for MoS 2 nanosheets to enhance photocatalytic hydrogen evolution
    Liu, Xia
    Hou, Yunhui
    Tang, Meng
    Wang, Longlu
    CHINESE CHEMICAL LETTERS, 2023, 34 (03)
  • [40] One-Pot Atom-Economic Synthesis of Thioselenophosphinates via a New Multicomponent Reaction of Secondary Phosphanes with Elemental Sulfur, Selenium, and Amines
    Artem'ev, Alexander V.
    Gusarova, Nina K.
    Malysheva, Svetlana F.
    Mamatyuk, Victor I.
    Gatilov, Yurii V.
    Ushakov, Igor A.
    Trofimov, Boris A.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (32) : 6157 - 6160
12345