Synthesis of Z-alkenes via visible light promoted photocatalytic E → Z isomerization under metal-free conditions

被引:71
|
作者
Cai, Wenbin [1 ]
Fan, Huaqiang [1 ]
Ding, Dazhong [2 ]
Zhang, Yongqiang [1 ]
Wang, Wei [1 ,3 ]
机构
[1] East China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China
[2] Qingdao Inst Food & Drug Control, Qingdao 266000, Peoples R China
[3] Univ New Mexico, Dept Chem & Chem Biol, Albuquerque, NM 87131 USA
关键词
PHOTOCHEMICAL-REACTIONS; ENERGY-TRANSFER; MECHANISMS; OLEFIN; METATHESIS; ACTIVATION; CATALYSTS; RING;
D O I
10.1039/c7cc07984b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A green approach for the synthesis of thermodynamically less stable Z-alkenes has been presented through the exploration of visible light promoted photocatalytic E-to-Z isomerization. This protocol features metal-free conditions, which is operationally simple, remarkably clean, and allows the synthesis of both electron-rich and electron-deficient Z-alkenes with diverse functional groups.
引用
收藏
页码:12918 / 12921
页数:4
相关论文
共 50 条
  • [41] Photocatalytic Cr(VI) reduction by metal-free photocatalysts under visible-light irradiation
    Xu, Xiahong
    Sui, Yan
    Chen, Wentong
    Li, Xiaodan
    Huang, Wei
    Chai, Lanxin
    Li, Yuntong
    Zhong, Hong
    JOURNAL OF ENVIRONMENTAL CHEMICAL ENGINEERING, 2024, 12 (06):
  • [42] Metal-Free Visible-Light Radical Iodoperfluoroalkylation of Terminal Alkenes and Alkynes
    Yajima, Tomoko
    Ikegami, Mako
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (15) : 2126 - 2129
  • [43] Facile metal-free visible-light-mediated chlorotrifluoromethylation of terminal alkenes
    Rao, V. Raghavender
    Patil, Kalpesh T.
    Kumar, Deepak
    Sebastian, Sharol
    Gupta, Manoj K.
    Shin, Dong-Soo
    MONATSHEFTE FUR CHEMIE, 2022, 153 (5-6): : 495 - 500
  • [44] Metal-Free Visible Light Hydroperfluoroalkylation of Unactivated Alkenes Using Perfluoroalkyl Bromides
    Yajima, Tomoko
    Shigenaga, Satsuki
    ORGANIC LETTERS, 2019, 21 (01) : 138 - 141
  • [45] STEREOSPECIFIC SYNTHESIS OF PURE [Z]-ALKENES AND [E]-ALKENES FROM ENAMINES VIA HYDROBORATION
    GORALSKI, CT
    SINGARAM, B
    RANGAISHENVI, MV
    BROWN, HC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1988, 195 : 242 - ORGN
  • [46] Peroxide promoted tunable decarboxylative alkylation of cinnamic acids to form alkenes or ketones under metal-free conditions
    Ji, Jing
    Liu, Ping
    Sun, Peipei
    CHEMICAL COMMUNICATIONS, 2015, 51 (35) : 7546 - 7549
  • [47] Visible Light Photocatalytic Metal-Free Perfluoroalkylation of Heteroarenes in Continuous Flow
    Straathof, Natan J. W.
    van Osch, Dannie J. G. P.
    Schouten, Arian
    Wang, Xiao
    Schouten, Jaap C.
    Hessel, Volker
    Noel, Timothy
    JOURNAL OF FLOW CHEMISTRY, 2014, 4 (01) : 12 - 17
  • [48] Visible Light Photocatalytic Metal-Free Perfluoroalkylation of Heteroarenes in Continuous Flow
    Natan J. W. Straathof
    Dannie J. G. P. van Osch
    Arian Schouten
    Xiao Wang
    Jaap C. Schouten
    Volker Hessel
    Timoth Noël
    Journal of Flow Chemistry, 2014, 4 : 12 - 17
  • [49] THE STEREOSELECTIVE HORNER-WITTIG REACTION WITH PHOSPHINE OXIDES - SYNTHESIS OF HINDERED Z-ALKENES VIA LUCHE REDUCTION
    HUTTON, G
    JOLLIFF, T
    MITCHELL, H
    WARREN, S
    TETRAHEDRON LETTERS, 1995, 36 (43) : 7905 - 7908
  • [50] Photocatalytic E → Z Isomerization of Polarized Alkenes Inspired by the Visual Cycle: Mechanistic Dichotomy and Origin of Selectivity
    Metternich, Jan B.
    Artiukhin, Denis G.
    Holland, Mareike C.
    von Bremen-Kuehne, Maximilian
    Neugebauer, Johannes
    Gilmour, Ryan
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (19): : 9955 - 9977