Visible-light photoredox-promoted desilylative allylation of α-silylamines: An efficient route to synthesis of homoallylic amines

被引:41
作者
Fan, Lulu [1 ]
Cheng, Fukun [1 ]
Zhang, Tingting [1 ]
Liu, Guoxing [2 ]
Yuan, Jinwei [1 ]
Mao, Pu [1 ]
机构
[1] Henan Univ Technol, Coll Chem & Chem Engn, Zhengzhou 450001, Peoples R China
[2] Henan Agr Univ, Coll Sci, Zhengzhou 450002, Henan, Peoples R China
基金
中国国家自然科学基金;
关键词
Visible-light photoredox catalysis; Homoallylic amines; Desilylative allylation; alpha-Amino alkyl radical; IMINO-ENE REACTIONS; AMINOALKYL RADICALS; DECARBOXYLATIVE ALLYLATION; ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITIONS; MEDIATED ADDITION; CATALYSIS; ACIDS; STRATEGY; COMPLEX;
D O I
10.1016/j.tetlet.2021.153357
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile and efficient synthesis of homoallylic amines by visible-light photoredox-promoted desilylative allylation of alpha-silylamines with allylic sulfones is described. A variety of alpha-silylamines derived from anilines, cyclic and acyclic alkyl amines reacted with a serious of mono or disubstituted allylic sulfones well to provide homollylic amines in good to high yields under very mild reaction conditions. (C) 2021 Elsevier Ltd. All rights reserved.
引用
收藏
页数:4
相关论文
共 71 条
  • [1] Photoredox-Catalyzed Site-Selective α-C(sp3)-H Alkylation of Primary Amine Derivatives
    Ashley, Melissa A.
    Yamauchi, Chiaki
    Chu, John C. K.
    Otsuka, Shinya
    Yorimitsu, Hideki
    Rovis, Tomislav
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (12) : 4002 - 4006
  • [2] Formal Allylic C(sp3)-H Bond Activation of Alkenes Triggered by a Sodium Amide
    Bao, Wei
    Kossen, Hanno
    Schneider, Uwe
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (12) : 4362 - 4365
  • [3] Diastereoselective allylation and crotylation of N-tert-butanesulfinyl imines with allylic alcohols
    Barros, Olga Soares do Rego
    Sirvent, Juan Alberto
    Foubelo, Francisco
    Yus, Miguel
    [J]. CHEMICAL COMMUNICATIONS, 2014, 50 (52) : 6898 - 6901
  • [4] Amine Functionalization via Oxidative Photoredox Catalysis: Methodology Development and Complex Molecule Synthesis
    Beatty, Joel W.
    Stephenson, Corey R. J.
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (05) : 1474 - 1484
  • [5] BORZILLERI RM, 1995, SYNTHESIS-STUTTGART, P347
  • [6] Heterogeneous Visible-Light Photoredox Catalysis with Graphitic Carbon Nitride for α-Aminoalkyl Radical Additions, Allylations, and Heteroarylations
    Cai, Yunfei
    Tang, Yurong
    Fan, Lulu
    Lefebvre, Quentin
    Hou, Hong
    Rueping, Magnus
    [J]. ACS CATALYSIS, 2018, 8 (10): : 9471 - +
  • [7] Olefin difunctionalizations via visible light photocatalysis
    Cao, Min-Yi
    Ren, Xiang
    Lu, Zhan
    [J]. TETRAHEDRON LETTERS, 2015, 56 (24) : 3732 - 3742
  • [8] Heterogeneous enantioselective catalyzed carbonyl- and imino-ene reactions using copper bis(oxazoline) zeolite Y
    Caplan, NA
    Hancock, FE
    Page, PCB
    Hutchings, GJ
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (13) : 1685 - 1688
  • [9] Transition-metal-free radical cleavage of a hydrazonyl N-S bond: tosyl radical-initiated cascade C(sp3)-OAr cleavage, sulfonyl rearrangement and atropisomeric cyclopropanation
    Chen, Yao-Zhong
    Liu, Teng
    Zhu, Jie
    Zhang, Hui
    Wu, Lei
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (24): : 3567 - 3573
  • [10] Studies Leading to the Development of a Single-Electron Transfer (SET) Photochemical Strategy for Syntheses of Macrocyclic Polyethers, Polythioethers, and Polyamides
    Cho, Dae Won
    Yoon, Ung Chan
    Mariano, Patrick S.
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2011, 44 (03) : 204 - 215