Ruthenium(II)-Catalyzed C-H Activation/Alkyne Annulation by Weak Coordination with O2 as the Sole Oxidant

被引:225
作者
Warratz, Svenja [1 ]
Kornhaass, Christoph [1 ]
Cajaraville, Ana [1 ]
Niepoetter, Benedikt [2 ]
Stalke, Dietmar [2 ]
Ackermann, Lutz [1 ]
机构
[1] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
[2] Univ Gottingen, Inst Anorgan Chem, D-37077 Gottingen, Germany
基金
欧洲研究理事会;
关键词
benzoic acids; C-H activation; dioxygen; oxidation; ruthenium; AEROBIC OXIDATIVE CYCLIZATION; CATALYZED DIRECT ARYLATIONS; BOND ACTIVATION; MOLECULAR-OXYGEN; ALKYNES; ALKENYLATION; PALLADIUM; ARENES; ACIDS; FUNCTIONALIZATION;
D O I
10.1002/anie.201500600
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Aerobic oxidative C-H functionalizations of weakly coordinating benzoic acids have been accomplished with versatile ruthenium(II) biscarboxylates under ambient oxygen or air. Mechanistic studies identified the key factors controlling the elementary step of the oxidation of the ruthenium(0) complex.
引用
收藏
页码:5513 / 5517
页数:5
相关论文
共 81 条
[1]  
Ackermann L., 2009, ANGEW CHEM, V121, P9976, DOI DOI 10.1002/ANGE.200902996
[2]   Assisted ruthenium-catalyzed C-H bond activation: Carboxylic acids as cocatalysts for generally applicable direct arylations in apolar solvents [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Althammer, Andreas .
ORGANIC LETTERS, 2008, 10 (11) :2299-2302
[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]   Robust Ruthenium(II)-Catalyzed C-H Arylations: Carboxylate Assistance for the Efficient Synthesis of Angiotensin-II-Receptor Blockers [J].
Ackermann, Lutz .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2015, 19 (01) :260-269
[5]   Cobalt-Catalyzed C-H Arylations, Benzylations, and Alkylations with Organic Electrophiles and Beyond [J].
Ackermann, Lutz .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (19) :8948-8954
[6]   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
[7]   Well-Defined Ruthenium(II) Carboxylate as Catalyst for Direct C-H/C-O Bond Arylations with Phenols in Water [J].
Ackermann, Lutz ;
Pospech, Jola ;
Potukuchi, Harish Kumar .
ORGANIC LETTERS, 2012, 14 (08) :2146-2149
[8]   Versatile Synthesis of Isocoumarins and α-Pyrones by Ruthenium-Catalyzed Oxidative C-H/O-H Bond Cleavages [J].
Ackermann, Lutz ;
Pospech, Jola ;
Graczyk, Karolina ;
Rauch, Karsten .
ORGANIC LETTERS, 2012, 14 (03) :930-933
[9]   Cationic Ruthenium(II) Catalysts for Oxidative C-H/N-H Bond Functionalizations of Anilines with Removable Directing Group: Synthesis of Indoles in Water [J].
Ackermann, Lutz ;
Lygin, Alexander V. .
ORGANIC LETTERS, 2012, 14 (03) :764-767
[10]   Ruthenium-catalyzed aerobic oxidative coupling of alkynes with 2-aryl-substituted pyrroles [J].
Ackermann, Lutz ;
Wang, Lianhui ;
Lygin, Alexander V. .
CHEMICAL SCIENCE, 2012, 3 (01) :177-180