Photoinduced Heterogeneous C-H Arylation by a Reusable Hybrid Copper Catalyst

被引：20

作者：

Choi, Isaac ^{[1
]}

Mueller, Valentin ^{[1
]}

Lole, Gaurav ^{[2
]}

Koehler, Robert ^{[3
]}

Karius, Volker ^{[4
]}

Vioel, Wolfgang ^{[3
]}

Jooss, Christian ^{[2
]}

Ackermann, Lutz ^{[1
,5
]}

机构：

[1] Georg August Univ, Inst Organ & Biomol Chem, Tammanstr 2, D-37077 Gottingen, Germany

[2] Georg August Univ, Inst Mat Phys, Friedrich Hund Pl 1, D-37077 Gottingen, Germany

[3] Univ Appl Sci & Arts, Lab Laser & Plasma Technol, Von Ossietzky Str 99, D-37085 Gottingen, Germany

[4] Georg August Univ, Geowissensch Zentrum, Goldschmidtstr 3, D-37077 Gottingen, Germany

[5] Georg August Univ Gottingen, Woehler Res Inst Sustainable Chem WISCh, Tammannstr 2, D-37077 Gottingen, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2020年 / 26卷 / 16期

基金：

欧盟地平线“2020”;

关键词：

C-H arylation; copper catalysis; heterogeneous catalysis; hybrid catalysis; photocatalysis; LIGHT PHOTOREDOX CATALYSIS; DIRECTING GROUPS; CROSS-COUPLINGS; BOND FORMATION; FUNCTIONALIZATION; ACTIVATION; PALLADIUM; BORYLATION; ALKYLATION; AMINES;

D O I：

10.1002/chem.202000192

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Heterogeneous copper catalysis enabled photoinduced C-H arylations under exceedingly mild conditions at room temperature. The versatile hybrid copper catalyst provided step-economical access to arylated heteroarenes, terpenes and alkaloid natural products with various aryl halides. The hybrid copper catalyst could be reused without significant loss of catalytic efficacy. Detailed studies in terms of TEM, HRTEM and XPS analysis of the hybrid copper catalyst, among others, supported its outstanding stability and reusability.

引用

页码：3509 / 3514

页数：6

共 50 条

[21] Electrochemical benzylic C-H arylation of xanthenes and thioxanthenes without a catalyst and oxidant
Gao, Hui
Chen, Xinyu
Wang, Pei-Long
Shi, Meng-Meng
Shang, Ling-Long
Guo, Heng-Yi
Li, Hongji
Li, Pinhua
[J]. ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (07): : 1911 - 1916
[22] Challenging Atroposelective C-H Arylation
Wencel-Delord, Joanna
Colobert, Francoise
[J]. SYNOPEN, 2020, 04 (04): : 107 - 115
[23] Advance in C-H Arylation of Indoles
Luo, Junfei
Xu, Xing
Zheng, Junliang
[J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (02) : 363 - 377
[24] Progress in Copper-Catalyzed Direct Arylation of Aromatic C-H Bonds
Liu, Wei
Bi, Yanlan
[J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (06) : 1041 - 1050
[25] C-H bond arylation of anilides inside copper-exchanged zeolites
Mathew, Bijoy P.
Yang, Hyun Ji
Jeon, Himchan
Lee, Jeong Hyeon
Kim, Jin Chul
Shin, Tae Joo
Myung, Kyungjae
Kwak, Sang Kyu
Kwak, Ja Hun
Hong, Sung You
[J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2016, 417 : 64 - 70
[26] DFT Studies on Copper-Catalyzed Arylation of Aromatic C-H Bonds
Wang, Meiyan
Fan, Ting
Lin, Zhenyang
[J]. ORGANOMETALLICS, 2012, 31 (02) : 560 - 569
[27] Copper-catalyzed free-radical C-H arylation of pyrroles
Honraedt, Aurelien
Raux, Marie-Audrey
Le Grognec, Erwan
Jacquemin, Denis
Felpin, Francois-Xavier
[J]. CHEMICAL COMMUNICATIONS, 2014, 50 (40) : 5236 - 5238
[28] Copper mediated decarboxylative direct C-H arylation of heteroarenes with benzoic acids
Patra, Tuhin
Nandi, Sudip
Sahoo, Santosh K.
Maiti, Debabrata
[J]. CHEMICAL COMMUNICATIONS, 2016, 52 (07) : 1432 - 1435
[29] A Meta-Selective Copper-Catalyzed C-H Bond Arylation
Phipps, Robert J.
Gaunt, Matthew J.
[J]. SCIENCE, 2009, 323 (5921) : 1593 - 1597
[30] A General Method for Copper-Catalyzed Arylation of Arene C-H Bonds
Do, Hien-Ouang
Khan, Rana M. Kashif
Daugulis, Olafs
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) : 15185 - 15192

← 1 2 3 4 5 →