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

被引：23

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 125 条

[1]

Ackermann L., 2009, ANGEW CHEM, V121, P9976, DOI DOI 10.1002/ANGE.200902996

[2] Copper-catalyzed "click" reaction/direct arylation sequence: Modular syntheses of 1,2,3-triazoles [J].

Ackermann, Lutz ;

Potukuchi, Harish K. ;

Landsberg, Dirk ;

Vicente, Ruben .

ORGANIC LETTERS, 2008, 10 (14) :3081-3084

[3] Catalytic arylations with challenging substrates: From air-stable HASPO preligands to indole syntheses and C-H-bond functionalizations [J].

Ackermann, Lutz .

SYNLETT, 2007, (04) :507-526

[4] C-H ACTIVATION Following directions [J].

Ackermann, Lutz ;

Li, Jie .

NATURE CHEMISTRY, 2015, 7 (09) :686-687

[5] Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].

Ackermann, Lutz .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295

[6] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Kapdi, Anant R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826

[7] Photoinduced, Copper-Catalyzed Alkylation of Amines: A Mechanistic Study of the Cross-Coupling of Carbazole with Alkyl Bromides [J].

Ahn, Jun Myun ;

Ratani, Tanvi S. ;

Hannoun, Kareem I. ;

Fu, Gregory C. ;

Peters, Jonas C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (36) :12716-12723

[8]

Bagal D.B., 2015, ANGEW CHEM, V127, P7105, DOI DOI 10.1038/NCHEM.1222

[9] Trifluoromethylchlorosulfonylation of Alkenes: Evidence for an Inner-Sphere Mechanism by a Copper Phenanthroline Photoredox Catalyst [J].

Bagal, Dattatraya B. ;

Kachkovskyi, Georgiy ;

Knorn, Matthias ;

Rawner, Thomas ;

Bhanage, Bhalchandra M. ;

Reiser, Oliver .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (24) :6999-7002

[10] A NEW FAMILY OF MESOPOROUS MOLECULAR-SIEVES PREPARED WITH LIQUID-CRYSTAL TEMPLATES [J].

BECK, JS ;

VARTULI, JC ;

ROTH, WJ ;

LEONOWICZ, ME ;

KRESGE, CT ;

SCHMITT, KD ;

CHU, CTW ;

OLSON, DH ;

SHEPPARD, EW ;

MCCULLEN, SB ;

HIGGINS, JB ;

SCHLENKER, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (27) :10834-10843

← 1 2 3 4 5 6 7 8 9 10 →