Copper-Catalyzed Hydrodefluorination of Fluoroarenes by Copper Hydride Intermediates

被引：83

作者：

Lv, Hongbin ^{[1
]}

Cai, Yuan-Bo ^{[1
]}

Zhang, Jun-Long ^{[1
]}

机构：

[1] Peking Univ, Beijing Natl Lab Mol Sci, State Key Lab Rare Earth Mat Chem & Applicat, Coll Chem & Mol Engn, Beijing 100871, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 11期

关键词：

C-F activation; copper; fluorine; homogeneous catalysis; hydrides; C-F BOND; CARBON-FLUORINE BONDS; ACTIVATION; RHODIUM; PENTAFLUOROPYRIDINE; HEXAFLUOROPROPENE; CP-ASTERISK-2ZRH2; PERFLUOROARENES; HYDROSILYLATION; FLUOROPYRIDINES;

D O I：

10.1002/anie.201208364

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Breaking bad: Efficient copper-catalyzed C-F bond activation has been achieved by replacing fluorine with hydrogen. A copper hydride is proposed as the active intermediate, which proceeds through a nucleophilic attack on the fluorocarbon, as determined by experimental and theoretical results (see structure; C gray, H white, Cu light red, F light blue; distances in Å). © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：3203 / 3207

页数：5

共 50 条

[21] Copper-Catalyzed Perfluoroalkylthiolation of Alkynes with Perfluoroalkanesulfenamides
Tlili, Anis
Alazet, Sebastien
Glenadel, Quentin
Billard, Thierry
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (29) : 10230 - 10234
[22] Copper-Catalyzed Regioselective Borylfluoromethylation of Alkenes
Wu, Nuo-Yi
Xu, Xiu-Hua
Qing, Feng-Ling
ACS CATALYSIS, 2019, 9 (06) : 5726 - 5731
[23] Copper-Catalyzed Semihydrogenation of Alkynes to Z-Alkenes
Semba, Kazuhiko
Kameyama, Ryohei
Nakaoa, Yoshiaki
SYNLETT, 2015, 26 (03) : 318 - 322
[24] Copper-Catalyzed Oxidation of Alkanes under Mild Conditions
Garcia-Bosch, Isaac
SYNLETT, 2017, 28 (11) : 1237 - 1243
[25] Copper-Catalyzed Olefin Aminoacetoxylation
Mancheno, Danny E.
Thornton, Aaron R.
Stoll, Armin H.
Kong, Aidi
Blakey, Simon B.
ORGANIC LETTERS, 2010, 12 (18) : 4110 - 4113
[26] Copper-Catalyzed Difluoroalkylation Reaction
Dong, Dao-Qing
Yang, Shao-Hui
Wu, Pei
Wang, Jin-Zhi
Min, Ling-Hao
Yang, Hao
Zhou, Meng-Yu
Wei, Ze-Hui
Ding, Cai-Zhen
Wang, Yan-Li
Gao, Jia-Hui
Wang, Shu-Jie
Wang, Zu-Li
MOLECULES, 2022, 27 (23):
[27] Copper-Catalyzed Hydrofunctionalization of Alkynes
Suess, Alison M.
Lalic, Gojko
SYNLETT, 2016, 27 (08) : 1165 - 1176
[28] Towards a Practical and Efficient Copper-Catalyzed Trifluoromethylation of Aryl Halides
Schareina, Thomas
Wu, Xiao-Feng
Zapf, Alexander
Cotte, Alain
Gotta, Matthias
Beller, Matthias
TOPICS IN CATALYSIS, 2012, 55 (7-10) : 426 - 431
[29] Copper-Catalyzed Innate Ethoxycarbonyldifluoromethylation of Electron-Rich Arenes
Belhomme, Marie-Charlotte
Bayle, Alexandre
Poisson, Thomas
Pannecoucke, Xavier
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (08) : 1719 - 1726
[30] Copper-Catalyzed Intramolecular Carbotrifluoromethylation of Alkynes for the Construction of Trifluoromethylated Heterocycles
Wang, Yanan
Jiang, Min
Liu, Jin-Tao
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (47) : 15315 - 15319

← 1 2 3 4 5 →