Semiheterogeneous Dual Nickel/Photocatalytic (Thio)etherification Using Carbon Nitrides

被引:103
作者
Cavedon, Cristian [1 ,2 ]
Madani, Amiera [1 ,2 ]
Seeberger, Peter H. [1 ,2 ]
Pieber, Bartholomaeus [1 ]
机构
[1] Max Planck Inst Colloids & Interfaces, Dept Biomol Syst, Muhlenberg 1, D-14476 Potsdam, Germany
[2] Free Univ Berlin, Dept Chem & Biochem, Arnimallee 22, D-14195 Berlin, Germany
关键词
OXYGEN-ATOM TRANSFER; REDUCTIVE-ELIMINATION; NITROUS-OXIDE; C-N; PHOTOREDOX; HYDROXYLATION; CATALYSIS; ARYL;
D O I
10.1021/acs.orglett.9b01957
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A carbon nitride material can be combined with homogeneous nickel catalysts for light-mediated cross-couplings of aryl bromides with alcohols under mild conditions. The metal-free heterogeneous semiconductor is fully recyclable and couples a broad range of electron-poor aryl bromides with primary and secondary alcohols as well as water. The application for intramolecular reactions and the synthesis of active pharmaceutical ingredients was demonstrated. The catalytic protocol is applicable for the coupling of aryl iodides with thiols as well.
引用
收藏
页码:5331 / 5334
页数:4
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共 39 条
[1]   Aerobic Copper-Catalyzed Organic Reactions [J].
Allen, Scott E. ;
Walvoord, Ryan R. ;
Padilla-Salinas, Rosaura ;
Kozlowski, Marisa C. .
CHEMICAL REVIEWS, 2013, 113 (08) :6234-6458
[2]   Selected Copper-Based Reactions for C-N, C-O, C-S, and C-C Bond Formation [J].
Bhunia, Subhajit ;
Pawar, Govind Goroba ;
Kumar, S. Vijay ;
Jiang, Yongwen ;
Ma, Dawei .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (51) :16136-16179
[3]   General and Efficient C-C Bond Forming Photoredox Catalysis with Semiconductor Quantum Dots [J].
Caputo, Jill A. ;
Frenette, Leah C. ;
Zhao, Norman ;
Sowers, Kelly L. ;
Krauss, Todd D. ;
Weix, Daniel J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (12) :4250-4253
[4]   The application of heterogeneous visible light photocatalysts in organic synthesis [J].
Chen, Jun ;
Cen, Jie ;
Xu, Xiaoliang ;
Li, Xiaonian .
CATALYSIS SCIENCE & TECHNOLOGY, 2016, 6 (02) :349-362
[5]   Triazine- and Heptazine-Based Carbon Nitrides: Toxicity [J].
Dong, Qi ;
Latiff, Naziah Mohamad ;
Mazanek, Vlastimil ;
Rosli, Nur Farhanah ;
Chia, Hui Ling ;
Sofer, Zdenek ;
Pumera, Martin .
ACS APPLIED NANO MATERIALS, 2018, 1 (09) :4442-4449
[6]   Strongly Reducing, Visible-Light Organic Photoredox Catalysts as Sustainable Alternatives to Precious Metals [J].
Du, Ya ;
Pearson, Ryan M. ;
Lim, Chern-Hooi ;
Sartor, Steven M. ;
Ryan, Matthew D. ;
Yang, Haishen ;
Damrauer, Niels H. ;
Miyake, Garret M. .
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (46) :10962-+
[7]   Palladium-catalysed hydroxylation and alkoxylation [J].
Enthaler, Stephan ;
Company, Anna .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :4912-4924
[8]   Metal-mediated C-O bond forming reactions in natural product synthesis [J].
Evano, Gwilherm ;
Wang, Jianjun ;
Nitelet, Antoine .
ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (12) :2480-2499
[9]   Heterogeneous photocatalytic organic synthesis: state-of-the-art and future perspectives [J].
Friedmann, Donia ;
Hakki, Amer ;
Kim, Hyejin ;
Choic, Wonyong ;
Bahnemannd, Detlef .
GREEN CHEMISTRY, 2016, 18 (20) :5391-5411
[10]   The toxicity of cadmium and resulting hazards for human health [J].
Godt, Johannes ;
Scheidig, Franziska ;
Grosse-Siestrup, Christian ;
Esche, Vera ;
Brandenburg, Paul ;
Reich, Andrea ;
Groneberg, David A. .
JOURNAL OF OCCUPATIONAL MEDICINE AND TOXICOLOGY, 2006, 1 (1)